When does a body of work reach completion? One answer is to end it by choice. This week in episode 356 you’ll hear the reasons behind our intentional ending of the Nerd Journey Podcast. We’ll rewind the clock and focus on the show’s trajectory and inflection points over time just like we’ve done for guests, share what we learned over the course of an 8-year journey from idea to consistently released show, and discuss our favorite moments. All of our content will remain online and accessible for listeners like you to go back and enjoy. Don’t miss our final call to action in this episode. Just because this body of work is complete, there is still work for all of us to do for our careers. Original Recording Date: 12-20-2025 Topics – A Purposeful Ending, Where We Started, Interview Format and Getting to Launch, The Why Behind the Ending, The Lessons We Learned, Our Favorite Moments, What to Expect from Us Moving Forward, There’s More to Be Done for All of Us. 1:01 – A Purposeful Ending We’ll give you the bottom line up front: this is the last episode of the Nerd Journey podcast. We still love the mission, but the time has come for us to complete this body of work. When we have interviewed guests on the show, we’ve talked through their career timeline and pulled out the lessons learned. Today, we’re going to do it for the show itself. 1:38 – Where We Started John was working as a sales engineer at VMware and was the co-host of the VMware Community Roundtable Podcast. He loved listening to podcasts, enjoyed the medium, and wanted to find a topic for a show. At the same time Nick was in the process of joining VMware, John and Nick were discussing all the things Nick needed to know to transition into sales engineering for a technology vendor. “In that conversation, I said ‘maybe we should start a podcast.’” – John White As Nick remembers it, this happened the weekend before Nick started at VMware in December 2017 (almost exactly 8 years before this episode’s recording). Nick wasn’t sure what he would talk about on a podcast. This suggestion from John started the ideation period, and our launch of the show was in July 2018. John talks about some of the initial ideas for the focus of the show. At that time, VMware podcasts and blogs were a great way to interact with the greater community. Doing something like this was also a way to become what John calls “nerd famous.” By the way, no one else can use that term now (trademarked by John). We initially considered talking about VMware news and our opinions on it since we both were going to be working at VMware. Both John and Nick came from small-to-medium business IT operations and eventually became sales engineers at a technology vendor. One of the things the show could be for is to talk about that journey and help others understand it was a possibility for them as well. John and Nick recorded about 10 episodes before launching to help hit the release cadence. Nick doesn’t remember why they chose a weekly release cadence but remembers the show launched while he was on vacation. John and Nick even recorded a podcast episode while Nick was on that vacation, which started a habit of Nick doing podcast work while on vacation. Because they had recorded so many episodes in advance, they were not going to be timely or points of authority on VMware technology. Both Nick and John’s roles were as technical generalists on the VMware side. “The only evergreen stuff that we had was the career stuff, so that became a little bit more the focus. I think that we were still thinking…we’ll just record more maybe VMware specific stuff later on…as that happens. For right now, here it is.” – John White Early episodes were very prescriptive about resumes and job interview processes at larger tech companies, for example. Nick points out that John had to carry the conversation in these early episodes because he was just learning to think about career focused topics (sort of like being new to lifting weights). But, Nick picked up a lot just from the conversations on the show. 7:50 – Interview Format and Getting to Launch Nick couldn’t remember what made them bring in guests originally, but Episode 13 with Tom Delicati was our very first guest interview on the show. John feels bringing in guests was always back of mind for him, and it was what he saw happen on the VMware Community Roundtable Podcast. “We’re just 2 people and we have our experience. But we can’t represent that as the full breadth of all of experience. That just doesn’t make any sense. So, we need to start exploring what other people’s career journeys have looked like and see if we can extract some knowledge and recommendations from that.” – John White Nick doesn’t remember having a prescriptive plan for interviewing guests but feels like they settled into long-form interviews as a style pretty quickly. John says this was a structure they hit upon in the beginning (talking through someone’s job history). The lessons learned from career inflection points like job transitions emerged from conversations with guests. John and Nick did not know this was going to happen when they began. Nick likes being able to highlight more of one specific guest’s story than otherwise could have been done if each interview was only 30 minutes with a guest. But we fully acknowledge people like different lengths of podcasts. “We wanted to tell interesting stories that had an arc: a beginning and an end and a journey in between. And we were able to find those even chopping people’s long 2-hour conversations up into 2 or even 3 episodes. I think that worked for us. I don’t know if it worked for everybody.” – John White “We probably spent the same time interviewing people as we would have. We just didn’t interview as many as if it had been 1 episode per person.” – Nick Korte We also didn’t want to release a 2-hour interview as one episode. That’s a lot of editing for just one episode release. People might not realize how much time goes into editing and production even after recording an interview. At the beginning, John had to give Nick advice on the kind of microphone to get. Nick started recording with a headset and then bought the same mic as John. They would each later invest in nicer microphones as the show progressed. “I knew nothing about editing and really not that much about how to make a podcast.” – Nick Korte, on beginning as a podcaster There were a lot of things we had to figure out just to make the podcast publicly available. John had researched some of the administrative things. He knew there was a WordPress plugin that could be used to turn MP3 files of released episodes into publicly available audio feed that would be the podcast. John says there were some mental blocks and hurdles he had to get through before launching the show, highlighting the fact that it took 6 months to go from idea to publishing. He was getting overwhelmed trying to figure out the back-end production and publishing process. John thinks it was Nick who kept asking what needed to happen for us to launch, and we went with WordPress and the plugin mentioned but never changed anything…because we had no time to go back. Nick and John learned that once you start a show and get it going, you will never run out of ideas. 13:58 – The Why Behind the Ending We never ran out of ideas. In fact, we still have ideas. So why are we stopping the podcast? We ran out of time. Nick has run out of time to work on editing and production. This has been a weekly show (up until the last couple months of our run), and it takes a large time commitment each week. For guest interview episodes, the intro and outro were not recorded at the same time the interview took place. These had to be recorded before the episode was released. The show notes are not AI-generated. Nick enjoyed writing them and adding in important links and references, feeling like it allowed him to remember the episodes better and internalize the lessons within them. Nick has a teenager now with many extracurricular activities and has had a workload increase at his job. “Probably for the last year I think I’ve been fooling myself at how much of a toll it’s been to just get an episode out each week.” – Nick Korte We even tried changing the release schedule to bi-weekly and have missed that cadence a couple of times. John ran out of time about 4 years ago and hasn’t had much time since to handle podcast related tasks. John experienced a job change and new baby at that time and couldn’t add anything else. He also moved at some point. John and Nick have been advancing in their own careers over time as well, which has added responsibility. John and his wife recently had a second child. He also left his job in June 2025 and has been doing a job search at the same time. Before Nick and John made this decision, Nick listened back to some previous episodes to get advice and perspective. Some of the advice that echoed the loudest came from Amy Lewis in Episode 302 – Ending with Intention: Once a Geek Whisperer with Amy Lewis (2/2). The idea of ending with intention stood out. “Rather than being spotty on our releases and not keeping our promise of how often we say we’re going to get the show out, we wanted to end it with intention and say, ‘ok, this is it.’” – Nick Korte “We haven’t lost the love of this task. We both want this to continue. But realistically, we can’t do it. And rather than sputter and peter out and never be heard from again, we just thought we’ll follow the lessons that we’ve learned from our bettors and do what they did. Let’s be intentional about the end.” – John White 18:02 – The Lessons We Learned John learned how much we can learn from the experience of others. He had ideas and biases about how we should handle specific aspects of our career, but doing the podcast allowed him to pressure test these ideas against the experience of others. John appreciates the breadth of background and experience our collective guests have brought to the show. It made him realize there are so many different ways to do certain things. Nick learned a ton about the mechanics of podcast production. It was around Episode 113 when Nick became the editor because John needed to take a break. If you want to hear more about how this happened, check out this blog post. Nick got hooked into podcast communities and even attended a podcast conference in 2025, meeting many other people who run their own podcast. Nick learned how much salesmanship is involved in getting a guest. You have to sell someone on the idea of being on the show and what they can bring to your listeners. How easy can you make it for them to say yes? John and Nick asked guests for 1.5 – 2 hours for an interview. “If you make it easy for someone to say yes and you build the outline of questions you might ask and you tell them what your show is about and what you want to cover, they’ll say yes. And they might give you more time than that…. I learned so much about different people that I never would have met otherwise. I am thankful for all the learnings of all the people who have been on the show. And I’m thankful for everything I’ve learned from you, John.” – Nick Korte John is grateful for the difference in skills he and Nick have and their ability to learn from one another just by co-hosting together. He likes to apply the idea of making it easy for others to say yes when he’s asking something of someone at work, for example. Nick learned how to beat perfectionism weekly. Something can always be edited more or re-recorded. There was a weekly ship date. “The deadline was always there to keep me honest.” – Nick Korte Seth Godin’s The Practice talks about keeping a promise to the people who follow you. Having a weekly release cadence meant we were promising to ship episodes weekly. “So, whether one person listened or a million people listened, we tried to keep that promise. And it was important to us to keep it, even if it was hard.” – Nick Korte “Having a million people listen to a specific episode or even hit the site in a specific week wasn’t the goal. I think the goal was the breadth of work and making it accessible and having people be able to benefit from it.” – John White We also had to learn how to tell people about the show in a clear, succinct way. When John or Nick would join video calls for work, people would see their microphones and ask if they had a podcast. We also used generative AI in our workflow for production a little bit, even if it was not for show notes. Doing the show has dragged with it some reasons to tinker with generative AI. With John’s help Nick learned how to build a Gemini prompt that would take the handwritten show notes and brainstorm titles, episode descriptions, and even create a prompt for a featured image based on the themes in the episode. John shares that we never wanted to use generative AI to take a transcript and generate an episode outline. We might lose touch with the content that way. John talks about the curse of being an audio editor. It’s impossible to NOT hear issues in other audio. Nick can hear mouth noises on Zoom calls like you wouldn’t believe. John says we can listen to someone else’s podcast and may be able to tell who is and is not the editor based on whether they speak into the microphone or move away from it and keep talking. 25:15 – Our Favorite Moments John says it’s hard to pick just one favorite moment. We got to meet some of our heroes in podcasting and other people who were “nerd famous” about their career stories. We had some great conversations with John Nicholson about how to evaluate a job offer and personal finance. Check out these for reference: Episode 224 – Tech Marketing, Interview Questions, and Executives as Wild Bears with John Nicholson (1/3) Episode 225 – Take Stock of Your Compensation with John Nicholson (2/3) Episode 226 – Negotiating Job Offers and Personal Finance Tips with John Nicholson (3/3) Having a podcast allowed us to have lengthy conversations with people who may not have otherwise had a reason to talk to us. John doesn’t think asking someone out of the blue for 2 hours of time without having a podcast would have worked well. John says he has a strong recency bias, often walking away from an interview with a guest thinking it was the best one yet. Nick’s favorite moments Nick remembers the first time we interviewed Mike Burkhart (in Episode 64 and Episode 65). He was having wifi issues and had to move everything into his living room floor to record the episode. John and Mike were kind enough to stay online and still do the interview. John and Nick live in different parts of the United States and have only been able to record together in person a handful of times. These times were special and rare. Nick remembers the time they recorded at VMware Explore and forgot to hit record…twice in a row! If John had to succumb to recency bias, he would pick the recent interview with Milin Desai. This set of interviews stands alone as the only time we were cold pitched a guest by someone we did not know, and it was a perfect fit. We got over 2 hours with a CEO! Episode 349 – Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3) Episode 350 – Scope and Upside: The Importance of Contextual Communication with Milin Desai (2/3) Episode 350 – Opt In: A CEO’s Take on Becoming AI Native with Milin Desai (3/3) People being both generous with their time and inciteful has been a pattern with guests. Nick and John got to have conversations with people both on the air and off the air. Nick appreciated having Dale McKay on the show (a mentor of his). You can find those episodes here: Episode 288 – Guardrails for Growth: A Mentor’s Experience with Dale McKay (1/2) Episode 289 – Enhance Your Personal Brand: Feedback as a Catalyst for Change with Dale McKay (2/2) Some other favorites from Nick: He enjoyed all of the conversations about the principal title and principal engineers. See also the principal tag for more of these stories. Nick also really enjoyed hearing the stories about why people went into leadership roles and why they moved away from them. One specific episode Nick highlights as a favorite is Episode 127 – Countdown to Burnout with Tom Hollingsworth (3/3). John mentions we all battle burnout from time to time, and having such great advice to go back to is a gift. Nick says being the editor is also a gift because you’re going to get to listen to the recorded discussion multiple times. Many times, the questions Nick and John asked in guest interviews were things they needed help with in their own careers. Hopefully the answers to those questions helped you as a listener too! John liked the fact that we were able to clip some of the times we messed up on the air and include those sound bites at the very end of an episode for people. To find these episodes, look for the Stinger metadata tag on an episode post. Nick mentions the Barry White intro stinger. It’s actually at the end of Episode 17. There are also some good stingers with guest Chris Williams. 31:05 – What to Expect from Us Moving Forward What are the things that will, won’t, and might happen in the future? The Nerd Journey site will remain online and accessible so our content will not disappear. You can still enjoy past episodes, browse the show notes, and leverage the Layoff Resources Page as well as our Career Uncertainty Action Guide. John and Nick can keep it online in a very cost-effective way just as they have to this point since the podcast was never monetized (not even Amazon affiliate links). John still has a dream of making sure we have transcripts of all the episodes and making these available in addition to the show notes. Maybe that could be extended to an AI chat bot that was trained on the transcripts. There would be some overhead involved in doing it, but John thinks it’s definitely possible. You can still reach out to John or Nick on LinkedIn or send us an e-mail. All current communication channels will remain in place. We are available for questions, if you want to talk, etc. We will definitely NOT restart this show. We have declared it complete. Even if we were going to do a show like this again in the future, we would do it differently. We might choose a different name, a different description, or a different format even. But we don’t have the time to do that right now anyway. We are NOT starting a new show (at least not right now). 34:59 – There’s More to Be Done for All of Us Just because the show is ending, that doesn’t mean your work is complete. None of our work is complete when it comes to career. “The things that we’ve talked about in curating your own career and being intentional about it always apply. We’re not going to be around to remind you of that every week, so I hope that people have learned those lessons and internalized them. But if not, do something to make those things intentional. You need to prioritize your career on a consistent basis.” – John White Here are some specific actions that you should take: Document your work. Generate proof of work. Show your work (similar to generating proof of work). John says this is what we were unconsciously doing when we began the podcast, sharing how we got to where we are and our job transitions so others can follow a similar path if they choose. The purpose of showing your work is so that others can learn from your experience and so you can remind yourself of what you’ve accomplished at a later time. Nick highlights that Episode 66: Three-Month Check-In as a Google Cloud Customer Engineer with John White, Part 1 remains the most downloaded episode in our catalog. Aim for small, iterative improvements. Turn information into knowledge. Some of this is through writing. We spoke several times on the show about writing being thinking, and it was specifically referenced in an episode with Josh Duffney – Episode 156 – Better Notes, Better You with Josh Duffney (1/2). Manage your knowledge in some kind of written form that isn’t in your head. Make it a knowledge management system of some kind. Practice Deep Work. It’s the most important work you can do because the skill of sustained attention will be the thing for which people are paid. Be mindful of technology waves and trends, and consider placing some small bets. Many guests have invested time and effort to become proficient in a newer technology before or as it was catching on. Don’t be afraid to tinker with those newer technologies. Consistently invest in your professional network. One way to do this could be via meetup groups or online communities. Reach out to use if you want to talk about careers, starting a podcast, or other fun topics. Nick can also tell you what it’s like to go through the John White School of Mentoring. We want to say a special thank you to every guest who took the time to be on the podcast and every listener who took the time to listen to an episode. If you’d like to read Nick’s reflection post about the show coming to a close, you can find it here – A Promise Kept: Choosing to Sunset the Nerd Journey Podcast. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Has organizational change redefined your job role? If it hasn’t yet, it will at some point. Whether acknowledged or ignored, every organizational change at a company impacts you. This is broader than just layoffs and more employees under a single manager. What are the organizational changes we might see, and what can we do to stand out and stay the course? This week in episode 355 we’re joined by guest Ryan Conley. Listen closely as we uncover different patterns of organizational change and provide practical tips to take action when those changes happen. Ryan helps us understand the corporate lifecycle and how to reframe this concept to understand where we are in the career lifecycle. You’ll hear from Ryan’s personal experience why the most resilient (and successful) technologists can identify and fill the gaps left after an organizational change whether that means working for a new boss, joining a different team, or changing job roles. Original Recording Date: 11-13-2025 Topics – Framing Our Focus on Organizational Change, Observations and Patterns, Defining the Career Lifecycle, When Colleagues Leave the Company, Layoff Resources, Working for a New Boss, Becoming Part of a Different Team, Shifting Job Roles or Job Level Changes, Parting Thoughts 2:58 – Framing Our Focus on Organizational Change Ryan Conley is a global field principal with 11p years of technical pre-sales experience. Before this, Ryan accumulated 13 years of systems administration in industries like education, finance, and consulting. In a recent episode of our show, guest Milin Desai compared organizations to living, breathing organisms that change. Nick posits that we don’t always think changes at our company will or can affect us as employees, but they do. Ryan references Aswath Damodaran’s writings about organizational change through the frame of a corporate lifecycle. We can relate by considering where our company might be in that lifecycle. As we experience the impacts of organizational change, Ryan encourages us to consider where we are in our career lifecycle. 4:19 – Observations and Patterns We see organizational change in different ways. What are some of the things Ryan has seen that he would classify as organizational changes? Let’s take a step back, past the current headlines, and look at the wider industry. Companies are growing inorganically (through mergers and acquisitions) or organically through investments in R&D (research and development), for example. Ryan has worked with companies that grew by acquiring 2 new companies each year to give an example. When you’re on the IT side of the acquiring company, there is a lot involved in the process like integrating e-mail systems, networks, and CRM systems. This process also involves getting 2 teams to work together. If one team needs to move from Office 365 to Gmail, it can be a big adjustment to employees’ daily workflow. The acquiring and acquired companies may have the same or very different cultures. In some cases, a company will want to acquire others with similar cultures, while some may not be concerned about the culture and choose to focus on the intellectual property (products or services, knowledge of how to build or manufacture something, etc.) of the company to be acquired. Nick says the experience for people on the side of the acquiring company and that of the company getting acquired can be quite different. Nick worked in IT for a manufacturing company for about 9 years, and over the course of his time there saw the company acquire several other companies. Nick usually had to go assess technology systems of companies that were going to be acquired and figure out how to integrate the systems in a way that would best service the user base. From what Nick has seen, some employees from the acquired company were integrated into the acquiring company, while others were eventually no longer with the company. Anxiety levels about an acquisition may be different depending on whether you work for the acquiring company or the acquired company. “The people are just as much of the intellectual property of the company as, in many cases, the actual assets themselves. And in some cases, that culture just isn’t a fit.” – Ryan Conley Ryan shares the example of someone he knew who left after another company acquired their employer because the culture was not a fit. Losing a key leader or a key subject matter expert after an acquisition could create a retention problem because others may want to follow them or start looking elsewhere. "So how do you protect the culture internally? How do you integrate a different culture in? But also, how do you kind of protect the long-term viability of the team as individuals, first and foremost, but then also the organization long-term? Depending on the intellectual property the acquiring company is after, we don’t usually know the level of due diligence completed to understand the key resources or subject matter experts who must be retained for longer-term success. Ryan encourages to imagine being the CTO or VP of Research and Development at a specific company that is suddenly acquired. People in these roles drive the direction of the technology investment for their company today as well as years to come. After being acquired, these people might be asked to work in lower levels of leadership with different titles, which could result in “title shock” and require some humility to accept. This scenario is a leadership change that happens as a result of an acquisition, but we might see leadership changes outside of acquisitions. Some leadership positions get created because of a specific need, others are eliminated for specific reasons, and some get shifted down or changed. Each of these changes has a downstream impact on individual contributors. Ryan talks about the positive impacts of leadership changes and gives the example of when a former manager was promoted to senior manager and allowed that person to hire a manager underneath him. There isn’t always internal mobility, but leadership changes could create these opportunities for individuals. Nick talks about the potential impact of a change in our direct boss / manager. If a boss who was difficult to work for leaves the company, getting a different boss could make a huge positive impact on our daily work lives. Similarly, we might have a great boss leave the company or take a different role, requiring that we learn to work for someone else who may operate very differently. Ryan tells us he has worked for some amazing leaders and says a leader is not the same as a manager. Ryan cites an example of getting promoted into a role that allowed him to have more strategic conversations about the focus of a team with his boss. We can choose to mentor members of our team so that when opportunities arise from structural change, they are equipped to seize those opportunities. Change can be viewed as an opportunity. A company’s overall priorities may have changed. Shifting priorities may require a company to operate very differently than it has in the past, which can cause changes to people, processes, and technology. Nick references a conversation with Milin Desai on constrained planning from Episode 351. Milin encourages regularly asking the question “is this still how we want to operate?” The way a company or team operated in the past may not be the best way to do it in the future. Changes to operations may or may not create opportunities for our career. Ryan loves this mindset of reassessing, which could apply to the company, a team, a business unit, the technology decision, etc. “I love the mindset of ‘what was best, why did we do it, and why was it best then?’ And then the follow up question is ‘is that still best today?’ And it’s ok if the answer is no because that leads to the next question – ‘how should we be doing it today…and why?’” – Ryan Conley, commenting on Milin Desai’s concept of constrained planning Ryan talks about companies reassessing their core focus. We’ve seen some companies divest out of a particular space, for example. Nick says this reassessment could result in a decision to pursue an emerging market which could lead to the creation of a new business unit and new jobs / opportunities for people. It could also go in the other direction where the company decides to shut down an entire business unit. 15:30 – Defining the Career Lifecycle Going back to the analogy Ryan shared about corporate lifecycle, we can reframe this and look at the career lifecycle. “Where are you at in your individual career journey? Where are you at in that lifecycle?” – Ryan Conley People close to retirement may be laser focused on doing well in their current role and hesitant to make a change. Others earlier in the career may want to do more, go deeper, or be more open to making a change. Ryan recounts speaking to a peer who is working on a master’s degree in AI. “With challenge comes opportunity, so do you want to try something new? And it’s ok if the answer’s no. But if there is an opportunity to try something new and you’re willing to invest in yourself and in your company, I think that’s worth considering.” – Ryan Conley We’ve talked to a number of former guests who got in on a technology wave at just the right time, which led to new opportunities and an entirely new career trajectory. Becoming aware of and developing expertise in emerging technologies can lead to new opportunities within your company (i.e. being able to influence the use of that technology within your company). “I think as technologists, whether you’re a business leader over technology, whether you’re day in / day out in technology as an individual contributor…emerging technology brings new challenges, just with a learning curve…. There’s hard skills that have to be learned. You get beyond the education it’s then also sharing with the peers around you…. So, what was best yesterday? Is it still best today? And tomorrow, we’ll ask the question again.” – Ryan Conley Ryan says this goes back to our analogy. Should we be doing certain things manually now, or is it better to rely on tools that can help automate the process? If we go back for a second to Ryan’s previous mention of integrating the technology stack for different companies, being part of the integration process might enable someone to learn an entire new technology stack. We might have to assess what is best between Google Workspace and Microsoft 365, for example, and develop the transition plan to move from one to the other and perhaps even capture the business case for using both within a company. To Ryan, this is an example of seeing a problem or gap and working to fill it. “If you want to be just a long-standing contributor to the team and your individual organization, I think it’s worth calling out…those who stick around longer and get promoted faster are the ones who see a gap and they plug it.” – Ryan Conley Ryan shares a personal story about a co-worker who attended a Microsoft conference on their own dime. This person worked over a weekend to setup a solution that saved the team significant time doing desktop imaging. But then, Ryan’s colleague took it a step further and trained the team on how to use it. Nick highlights the fact that we should remember to document our accomplishments to keep track of how we’ve changed as a result. We can use this information when searching for new opportunities or even in conversations with our leader. 20:34 – When Colleagues Leave the Company Another form of organizational change we’ve seen is outsourcing specific business functions. Daniel Paluszek spoke about companies outsourcing functions outside of their core business in Episode 338. If IT is outside the core business, a company might decide to outsource it. It doesn’t mean that’s the right decision, but it could be a possibility. Companies may outsource other functions like HR and payroll as well to give other examples. If IT was internal and it gets outsourced, that is an organizational change and will affect some people. Similarly, insourcing a function which was previously outsourced will have an impact. Ryan has learned in the last few years that some people are more adaptable to change than others. “And it’s not just looking at the silver lining. It’s recognizing the change. Maybe there’s a why, and maybe there isn’t a why. Or maybe the why hasn’t been clearly articulated to you. Being able to understand, what does this mean to me…. As an organization do I still believe in them? Do I still believe in the technology as a technologist? Do I still enjoy the people I work with? Those are all questions that come up, but ultimately you have to decide…is this change I want to roll with? Is this change I don’t want to roll with?” – Ryan Conley To illustrate, Ryan gives the example of a peer who left an organization after seeing a change they didn’t like in order to shift the focus of their role from technology operations to more of a site reliability engineering focus. While this type of change that results in a talented individual leaving an organization can be difficult for teammates to accept and for a manager to backfill, these types of changes that are beneficial to someone’s career should be celebrated. When we assess whether the changes made at a company are those we can accept and roll with, we can first make sure we understand what we are to focus on as individuals operating within the organization. We have an opportunity to relay that to other members of our team for the benefit of the overall team culture and to build up those who do not adapt to change well. Understanding organizational changes and what they mean for individuals may take repetition. While Ryan understands that he responds well to change, he remains empathetic to those folks to need to hear the message a few times to fully understand. Nick says we can learn from the circumstances surrounding someone leaving the company. For those we know, what interested them about taking a role at another company? Perhaps they took a role you’ve never thought about for yourself that could be something you pursue in the future. If a member of your team leaves the company, sometimes their role gets backfilled, and other times it may not. If the role is backfilled, you get to learn from a new team member. If not, the responsibilities of the departing team member will likely be divided among other team members. Though it would result in extra work, you could ask to take on the responsibility that would both increase your skill set and make you more valuable to the company. When Ryan worked for a hedge fund, the senior vice president left the company. This person was managing the company’s backups. Ryan had experience in this area from a previous role at a consulting firm and volunteered to do it. Shortly after taking on this responsibility for backups, he found that restoring backups from tape and needing to order new servers posed a huge risk to the company in a disaster scenario (i.e. would take weeks to restore everything). Ryan was able to write up a business plan to address the business continuity risk and got it approved by the COO. “Being able to see a gap and fill it is the central theme, and that came from change.” – Ryan Conley Ryan says if you’re willing to do a little more work, it is worth the effort to see a gap and work to fill it. 27:34 – Layoff Resources We acknowledged some of the byproducts of organizational change like layoffs and flatter organizations in the beginning of our discussion. We are not sidestepping the fact that layoffs happen, but that is not the primary focus of our discussion today. Here are a few things that may help if you find yourself being impacted by a layoff: First, know that you are not alone in experiencing this. “When a layoff hits, it’s important to remember…it’s extremely rare that that’s going to be personal. Once it’s firmly accepted, look for the opportunity in a forced career change. It’s there.” – thought shared with us by Megan Wills Check out our Layoff Resources Page to find some of the most impactful conversations on the topic of layoffs on our show to date. We also have our Career Uncertainty Action Guide with a checklist of the 5 pillars of career resilience as well as reusable AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed. 28:43 – Working for a New Boss Let’s move on to section 2 of our discussion. If you’re still at a company after an organization change has happened, we want to talk through some of the ways you can take control, take action, and succeed. We want to share a thought from former guest Daniel Lemire as we begin this discussion: “Companies are the most complicated machine man has ever built. We build great machines to accomplish as set of goals, objectives, or outputs. The better you can understand the value the company delivers…the faster you can understand where you fit in that equation. If you don’t understand where you contribute to that value, there’s work to be done. That work may be on you, may be on your skills, or perhaps it’s your understanding of where you fit into that equation.” – Daniel Lemire Let’s say that you’re impacted by an organizational change and will be working for a new boss. What can we control, and how to we make a positive impact? Ryan says we can be an asset to the team and support larger business goals by first giving some thought to who the new boss is as a person. Try to get to know them on a personal level. Ryan wants to get to know a new boss and be able to ask them difficult questions. Similarly, he wants a boss to be able to ask him difficult questions. Meeting a new boss face-to-face is ideal if that is possible, but this can be more difficult to arrange if your boss lives a large distance from you. Make sure you understand the larger organization’s mission statement. As individual contributors, we may lose sight of this over time. “If that is important to the team and the culture, I think it’s worth making sure you’re aligned with that. I think it’s worth understanding your direct manager’s alignment toward that and then having that kind of fuel the discussions…. What are you expecting of me? Here are my expectations of you as my manager. Where do you see change in the next 6, 12, 18 months?” – Ryan Conley, on using mission to drive conversations with your manager A manager may not have all the answers to your questions. They could also be inheriting a new team. Ryan encourages us to ask how we can help our manager to develop the working relationship further. This is something he learned from a previous boss who would close every 1-1 with “is there anything else I can do to help?” Nick says a manager may be able to contextualize the organization’s mission statement for the team and its members better than we can do for ourselves. For example, the mission and focus of the team may have changed from what it once was. A new manager should (and likely will) set the tone. Nick would classify Ryan’s suggestions above as seeking to learn and understand how your new manager operates. Back in Episode 84 guest Brad Pinkston talked about the importance of wanting to know how his manager likes to communicate and be communicated with. This is about understanding your manager’s communication preferences and can in some ways help set expectations. A manager may be brief when responding to text messages, for example, because they are in a lot of meetings. But if they tell you this ahead of time, it removes some assumptions about any hidden meanings in the response. Ryan gives the example of an executive who used to respond with Y for yes and N for no to e-mails when answering questions. We can also do research on a new boss in advance. We can look on LinkedIn to understand the person’s background and work history. We can speak to other people inside the company to see what they know about the person. Ideally, get a perspective from someone who has worked for the manager in the past because a former direct report might be able to share some of the context about communication preferences and other lessons learned from working with that specific manager. We can also try to be mindful of how the manager’s position may have changed due to organizational flattening. They may have moved from managing managers to having 15 direct reports who are individual contributors, for example. “Their time might be stretched thinner, and they’re just trying to navigate this new leadership organizational change with you.” – Ryan Conley The manager may or may not have wanted the situation they are currently in. How is your boss measured by their boss, and how can you help them hit those metrics? You may not want to ask this in the first 1-1, but you should ask. Ryan suggests asking your boss what success looks like in their role. You can also ask what success for the team looks like in a year and what it will take to get there. Based on the answer, it might mean less 1-1s but more in depth each time, more independence than you want, or even more responsibility than you wanted or expected. Ultimately, by asking these questions, you’re trying to help the team be more successful. We want our manager to understand that we are a competent member of the team. Understanding what success looks like allows us to communicate with our manager in a way that demonstrates we are doing a good job. Some of the time in our 1-1s with a manager will be spent communicating the things we have completed or on which we are actively working. We need to demonstrate our ability to meet deadlines, for example. Daniel Lemire shared this book recommendation with us – The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter. It’s a great resource for new leaders but also excellent for individual contributors. Ryan tells us to keep track of our wins over the course of any given year (something that was taught to him) so we have it ready for performance reviews. He encourages keeping a journal that we start in January. Keep track not only of what you did but the outcomes your work delivered and the success metrics. For example, if you gave a presentation, note the number of people present. The company culture may have some impact on the language you need to use to word your accomplishments (i.e. using “I” statements). “I didn’t want to be the only person who could do it. I’d rather learn it and then enable 5 other people to do it. And then those 5 people go do it, and that is a much bigger outcome.” – Ryan Conley, on the outcome of efforts at work and being a force multiplier Have a journal of the things you do at work that you update consistently. This could be screenshots, a written description, etc. “What are the metrics that you should be tracking? Mentally think about that because…when you have your annual review, you’re going to miss something. You’re going to miss a detail. You’re going to miss an entire line item versus if you started in January and you just get into the practice of ‘I did this.’ And then when you’re having your first annual review with this brand-new manager, it’s far easier to have a more successful conversation.” – Ryan Conley, on the importance of documenting our work in a journal somewhere Ryan reminds us it is ok to use generative AI tools to check our work. Use multiple different tools to get suggestions on how you might want to phrase the outcomes you delivered and the metrics you tracked. Nick says we should document our accomplishments as Ryan mentioned, but we should make sure we keep a copy of them so that we do not need to rewrite them from nothing in the event we are impacted by a layoff. If the journal containing all of your accomplishments is sitting in the corporate OneDrive or cloud storage, you will lose access to it when you leave the company. Be sure you have a disaster recovery plan for your accomplishments! The new boss is probably going to have team calls of some kind. While what you experience may vary from this, in Nick’s experience the first time a manager hosts a call with their team they will share some career background, how they operate, and give team members some idea of what to expect. This kickoff team call usually happens before 1-1s begin. Listen really carefully when this first team call happens. Write down some questions you can ask the boss in that first 1-1 conversation. The manager will have to lead that first 1-1 conversation a little bit, but coming into it prepared with questions will be far easier than trying to think of questions in the moment. A simple follow up question Ryan suggests is how the manager wants to handle time off. Is there a shared team calendar, a formal process, carte blanche, specific blackout dates to be aware of, etc.? We can handle the simple things about how this new manager operates and what their values are early on in our working relationship. Ryan tells us he learned far too late to ask how managers handle promotion / raise / career growth conversations. One of Ryan’s past managers scheduled a quarterly checkpoint to specifically talk about career growth items. Ryan was in charge of making the agenda in advance, and his manager would come prepared to talk about each agenda item. It’s ok to ask for these regular career discussions. If your manager has a large team, these may be less frequent than otherwise. Ask the manager about the best way for both you and them to come into these discussions prepared. Nick likes the idea of an individual owning the agenda for these conversations. Nick tells us about a manager who sent out 1-1s to team members and provided a menu of options for the types of things that could be discussed during the 1-1 time in the body of the meeting invitation. It helps give people ideas for things to discuss but also lets them know the overall intention of the 1-1s. For the very busy manager, we could ask to use a specific 1-1 to talk about career-related items rather than in a separate meeting (if needed). Nick mentions a recent episode of Unicorns in the Breakroom Podcast in which Amy Lewis talks about using a shared document for 1-1s to hold an employee accountable for bringing agenda items and to document what transpired in previous conversations. Along the lines of trying to be helpful to a new manager, ask how they want to handle team calls when on vacation. Will team calls be cancelled when the manager is on vacation, or are they looking for team member volunteers to host these calls? This may be an opportunity to step up and do more if you want that, especially if you want to gain some leadership experience. Ryan tells us at one point he was a team lead, and part of his responsibility was leading team calls in his manager’s absence. This involved leading the call, taking notes, and taking action on follow up items from the meeting. We should bring up time sensitive items to the boss quickly, especially if something needs attention. Communicate things that have a financial impact to the company (a subscription renewal, drop dead due date to exit a datacenter facility, point at which access to something will be lost, etc.). Do not assume your manager knows if you are unsure! Ryan recounts a story from earlier in his career when a CFO wanted a specific number of users added to the Exchange server. There were several cascading impacts of completing this task that went well beyond the scope of licensing and involved procuring more hardware. Ryan took the time to explain the implications. “This is a simple ask. You want the answer to be yes, but I’m going to give you more context…. There is a deadline. I want to make sure we hit it as a team, but there are some implications to your ask. I want to make sure you’re fully aware.” – Ryan Conley, on giving more context to leadership Share what you have in flight and the priorities of those items. The new manager may want you to change the priority level on some things. 45:21 – Becoming Part of a Different Team You could end up working on a completely different team of peers as a result of organizational change. You might work on the same team as people you already know but might not. You may or may not work for the same boss. Ryan and Nick have experienced very large reorganization events and ended up in different divisions than they were previously. Ryan had a change of manager, change of a peer he worked closely with, and joined a new team of individuals reporting up to the same boss all at once. “A little bit of the tough lesson is you go into a bigger pond…. I think it’s ok to take a moment and pause. For me, I had to kind of reassess and kind of figure out…what are these changes? What are the new best ways to operate within this new division so to speak? …within my team, no one on my prior team was on my team, so it was like this whole new world.” – Ryan Conley After this change, Ryan saw an opportunity to go deeper into technology and chose to take a different role. Ryan worked for a new (to Ryan at least) leader who was very supportive of his career goals. This leader helped Ryan through the change of roles. “If you do good work, even through change…if you’re identifying gaps, you’re filling it, you’re stepping up where the team needs you to step up, you’re aligning with the business direction to stay focused…I think there can still be good outcomes even if in the interim period you’re not 100% happy.” – Ryan Conley If you don’t know anyone on your new team, you have an entire set of people from which you can now learn. Does your job function change as a result of joining this new team? Make sure you understand your role and its delineation from other roles. Maybe you serve larger customers or work on different kinds of projects. Maybe you support the technology needs of a specific business unit rather than what we might deem as working in corporate IT. Maybe you focus on storage and high-level architecture rather than only virtualization. It could be a chance to learn and go deeper in new areas. Did the focus of the overall team change (which can trickle down and impact your job function)? Maybe you’re part of a technology team that primarily manages the outsourced pieces of the technology stack for your company. So instead of working with just employees of your company you now work with consulting firms and external vendors. Ryan says we can still be intentional about relationships and he illustrates the necessary intentionality with the story behind his pursuit of a new role. Ryan was intentional about his desire to join a new team after the reorganization, but it didn’t work out on the timeline he wanted. He remained patient and in constant, transparent communication with a specific leader who would eventually advocate for him with the hiring manager. Just doing our job can be difficult when we’re in a challenging situation like a manager we do not get along with, trying to evolve with a top-level strategy change, etc. This can involve internal politics. Stay the course. Ryan tells us about a lesson he learned when interviewing for a new role he wanted. “Maybe be a little bit more vocal. Pat yourself on the back in a concise way. Again…go back to your journal, know your metrics, and stick by them.” – Ryan Conley, on interviewing and humility Nick says the intentionality behind building relationships applies to your relationship with your boss (a new boss or your current boss that has not changed). This also applies to new teammates! What are the strengths in the people you see around you? Who volunteers to help? Who asks questions when others will not? Ryan shares a story about 2 peers who on the surface seemed to disagree a lot but ended up making each other better (and smarter) by often taking opposing sides on a topic. When one of them left the company, the other person missed getting that perspective and intellectual challenge. Ryan suggests we pay attention to the personalities of team members and the kinds of questions they ask. If a specific teammate tends to do all the talking in meetings, find ways to enable others to speak up who have valuable perspectives but may be quieter. This at its heart is about upleveling others. We can do that when we join a new team, but we can also do this for former teammates by keeping in touch with them over time. This could apply to former teammates who still work at the same company as well as those who have left the company. Ryan tells us a story about when he first made the transition from working in IT operations to getting hired at a technology vendor in a very different role. “It’s very different being face-to-face as a consultant, face-to-face as a vendor. And I had a buddy. He started going back 11 years almost to the day here. We were each other’s lifeline…. He would have a bad day, and he would call me. Most of the time I was just there to listen…. And then the next week it was my turn, and I would call him…. So having a buddy in these change situations I think is a great piece of advice.” – Ryan Conley It can be easy to fall out of touch with people we no longer interact with on a daily or weekly basis. This takes some effort. We’ve met people who try to setup a 1-1 with someone in their professional network once every 1-2 weeks. Ryan has a tremendous amount of empathy for others who have recently had a child, for example. We can buddy up with specific professional or life experience and take the opportunity to learn from them. Ryan refers to building an “alumni network” of people you want to remain close with over time. While this helps build our own set of professional connections, we can do this by mentoring others as well (a chance to give back, which is usually much less of a time commitment than we think). Ryan has mentored a number of new college graduates and managed to keep up with their progress over time. Listen to the way he describes the career progression of his mentees and the long-term relationships it produced. We might be mentoring others (on our own team or beyond). This could act as relatable experience for a future role as a team lead or people manager, but highlighting this experience to your manager is something you should do in those career conversations. In those 1-1s with your manager you are asking how you are doing but also how you can do better. Sometimes that means doing more of something you have done in the past. Ryan reminds us that the journal is a tracking mechanism for specific actions and their impact. Whether it’s mentoring or helping the manager with hiring or candidate evaluation, be sure to track it! There might be a gap in expertise on your team that you can fill (either because you have a specific skill or because you learned a new skill to fill that gap). When joining a new team, do some observing and stay humble before you declare there is a gap and that you are the one to fill it. Ryan says we can raise gaps with our manager. For example, maybe there is only one person on the team who knows how to do something. Could you pair with that person and cover them while they are on vacation? “I think it goes back to recognizing that you cannot learn it all and then revaluating…what do I need to learn? So, there’s certain functions that you have to know how to do, and that’s where your manager’s going to help you set those expectations…. We’re in technology, so as a technologist, what do you want to learn? What do you want to do more of? And that could be a gap that you see, and you have that conversation….” – Ryan Conley If there is not an opportunity at work to learn what you want to learn (i.e. your manager might not support you doing more of specific work, etc.), you can learn it on your own time and then re-evaluate longer term what you want to do. 59:46 – Shifting Job Roles or Job Level Changes We talked about this a little bit earlier. Maybe you stay an individual contributor, move into leadership, or change leadership levels entirely within an organization. Ryan talks about the new expectations when you change your daily role. There are expectations we put on ourselves and those expectations put on us by our leaders. There are both opportunities and challenges. Ryan shares that he has been approached in the past to lead a team, but when this has happened, he took the time to think through what he wanted (his career ladder, his motivations, and his desired focus). “Leading people is not something that I want to currently focus on. I know what I’m motivated by. I’m a technologist at heart. I want to keep learning, and I personally like the technology that I’m focused on right now. And it’s not that leadership would necessarily remove technology entirely…. It’s just it would be a different focus area. And I think in your career journey it’s worth just kind of keeping tabs on where you’re at in your career (the ladder of change that we keep mentioning, that lifecycle)…. Do you want to go up the ladder as part of your lifecycle and get into a management role? I think mentorship can be very fulfilling. I think leading people can be very fulfilling. But in my case, I’ve decided I still want to stay an individual contributor. There’s still aspirations that I have there….It’s ok to say no is really what I’m getting at…. Really think about the job that you’re in at the company that you’re in. What are the opportunities within? What motivates you? And stay true to that.” – Ryan Conley Ryan has said no to being a people leader as well as to technical marketing roles. He had a desire to get through the principal program. He encourages listeners to think about whether they would be happy in 1-2 years if they took a new role before making the final decision. Nick mentions the above is excellent when you have the choice to take a new role. But what if it’s forced on you as the result of an organizational change? We can recognize where we are in the career lifecycle even if an organizational change places us in a new role that was not our choice. Make sure you understand what the new role is, and think about how you can align it with where you are in the career lifecycle (including the goals you have and the things you want). Nick had a manager who encouraged his team to align their overall life purpose to the current job role or assignment. In doing this, it will be easier to prevent intertwining your identity with your job or your company. We may have to put out heads down and just do the work for a while. But maybe there is an opportunity to align with the things you want and the type of work you want to do which is not immediately obvious. In this job market, if you are employed, be thankful and do a great job. Ryan hopes listeners can think back to an unexpected change that happened which led to new opportunities later. “Pause, recollect, align your focus with your new manager, align your focus with either the changing mission statement or the current mission statement…. What is fulfilling you personally (your own internal values)? If they are being conflicted, I think there’s a greater answer to some of your challenges, but they’re not being conflicted how can you be your best self in a company without the company being all of yourself? …The cultural identity of the workplace and the home can sometimes be a little too close, a little to intertwined…. Maybe you’re just way too emotionally invested in your day job and it’s just a good moment to reset…. What is your value system? Why? And then how can you be your best self in your workplace? And I think far too often we want to have our dream job…. ‘A dream job is still a job. There are going to be days when it is just a really difficult day because it’s a really difficult job. It’s still your dream job, but every job is going to have a difficult day.’” – Ryan Conley Every job will be impacted by some kind of organizational change multiple times throughout your career. 1:06:18 – Parting Thoughts Ryan closes with a funny anecdote about a person who worked on the same team as him that he never had the chance to meet in person. In this case, the person invested more in their former team than meeting members of their new team. Maybe a good interview question for those seeking new roles could be something about organizational changes and how often they are happening at the company. Ryan encourages us to lead with empathy in this job market and consider how we can help others in our network who may be seeking new roles. Ryan likes to share job alerts on LinkedIn and mentions it has been great to see the formation of alumni groups. “Share your rolodex. Help people connect the dots. And lead with empathy.” – Ryan Conley To follow up on this conversation with Ryan, contact him on LinkedIn. Mentioned in the Outro A special thanks to former guest Daniel Lemire and listener Megan Wills for sharing thoughts on organizational change that we were able to include in this episode! Ryan told us we can lead with empathy when helping others looking for work in this job market, but Nick thinks it’s empathy at work when we’re asking a new boss or team member how we can help. If you want to bring more empathy to the workplace, check out Episode 278 – Uncovering Empathy: The Greatest Skill of an Inclusive Leader with Marni Coffey (1/3) in which guest Marni Coffey tells us about empathy as her greatest skill. It’s full of excellent examples. If you’re looking for other guest experiences with organizational change, here are some recommended episodes: Episode 210 – A Collection of Ambiguous Experiments with Shailvi Wakhlu (1/2) – Shailvi talks about a forced change of role that was actually an opportunity in disguise Episode 168 – Hired and Acquired with Mike Wood (1/2) – Mike Wood’s company was acquired, and the amount of travel went up soon after to increase his stress. Episode 169 – A Thoughtful Personal Sabbatical with Mike Wood (2/2) – Mike Wood shares another acquisition story that this time ended with him taking a sabbatical. Episode 84 -Management Interviews and Transitions with Brad Pinkston – Brad Pinkston shares what he likes to do when working for a new boss. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Imagine your work day starting off like any other only to find you’ve been laid off. What would you do next? Dave Stevens lived this reality a couple of years ago and joins us this week in episode 354 to share the lessons from that experience. We’ll take you through how Dave processed the news of being laid off, the warning signs he missed, when he knew it was time to begin searching for a new role, how he thought about what to do next, and the critical importance of his personal and professional network throughout this process. Regardless of your age or the size of your professional network, Dave shares actionable suggestions for building professional connections that we all may be overlooking. Original Recording Date: 10-28-2025 Topics – Background and the Impact of a Layoff Event, Initial Forward Progress and Reliance on a Professional Network, Skills Gaps and Unexpected Positives, Elements of the Personal and Professional Network, Reaching Closure and Reflecting Back on the Lessons 2:27 – Background and the Impact of a Layoff Event Dave Stevens is a Field Solutions Architect at Pure Storage. In this role, Dave is a technical overlay for pre-sales technical personnel at Pure across North America. This is the role Dave took after he was impacted by a layoff. What was Dave’s role before he was impacted by a layoff event? For context, the layoff event we discuss in this episode took place around 2.5 years before this recording. Dave was classified as a systems engineer or pre-sales technical resource at his employer supporting multiple account reps. It was more of a solutions architect type of role, and Dave highlights his entry into this organization and role was via acquisition. Was there an element of technical marketing to the role? Nick mentions that Dave often had to attend trade shows in this role. Dave had a virtualization background and went to a lot of events to discuss how his company’s products integrated with those different technology ecosystems. The day Dave was laid off started as a normal day at his home office. His boss was based in Europe, so most 1-1 calls were usually late in the day his boss’s time (early afternoon for Dave). A meeting popped up that was earlier than usual, but Dave didn’t think anything of it. Right after Dave joined the remote session for the meeting, someone from HR joined followed by Dave’s boss. Dave wasn’t quite sure what to expect and didn’t know what was happening. He didn’t know if it was a layoff coming or some other kind of situation happening at his company. When Dave was laid off, they told him it was not for performance reasons, but there weren’t really any other details provided on why he was being laid off. “So, at that point it was just like, ‘what do I do?’” – Dave Stevens, on receiving layoff news After receiving the news, Dave’s access to company systems like e-mail was quickly cut off. He went downstairs and spent the rest of his day relaxing. Dave did not want to talk about what happened any further that first day. Did Dave struggle with separating his identity from his employer or the job he held at all when this happened? Dave says he did, at least a little bit. Dave wanted to be successful in whatever role he found himself, and the reason he was in the systems engineering role at the time of the layoff event is a result of his drive to be successful in the years leading up to that role. “I also wanted to make sure that…the people that I worked with that I enjoyed working with. If I didn’t enjoy working with them, then there was no reason to continue staying there. So that’s part of my identity on how I interact with work.” – Dave Stevens In the early days of Twitter (now X), Dave defined an identity there. He also created a personal blog. Dave says his identity was often tied to where he worked. “Once this all happened, I just kind of cut that off. And I needed some time to really digest what I just went through that day.” – Dave Stevens Is there something Dave wishes people had done for him when this first happened? Dave says he wishes he would have listened to his wife. Before experiencing the layoff event, a number of colleagues who had entered the company through acquisition like Dave were either leaving or had been laid off (including his boss being laid off). At the time, Dave didn’t think much about these events. Dave’s wife had encouraged him to look for other jobs before the layoff happened, and he feels he should have listened. “It’s much easier finding a job when you have a job. There’s not as much pressure on you. You can take your time and really find the job that you want. That’s the one thing that kind of took me by surprise….” – Dave Stevens Did Dave’s wife also point him in a direction or provide feedback on the type of work he should pursue? We’ve spoken to previous guests who had spouses that provided insight into the type of work that made them happy. Dave feels like there has been an element of this in place since he and his wife got married. When Dave got a job opportunity to relocate to the New Hampshire area, his wife had some interesting feedback. “It’s great that you’re going to make more than you’re making at the job you are currently, but I don’t want you to take a job just because of money. I want you to take a job because it’s something you’re interested in doing and you’re going to be happy at. So, I’ve always kept that in the back of my mind every time I go and look for a job….” – Dave Stevens, quoting his wife’s advice Dave considered this same advice when pursuing his current role at Pure. Because he enjoyed meeting and speaking with people during the interview process, the decision to accept the role was easy. Liking the people he would be working with was more important than a pay increase. 10:53 – Initial Forward Progress and Reliance on a Professional Network How long did Dave need to process before taking the first actions toward a new role? For the first 3 weeks or so, Dave relaxed a little bit. There were a number of projects at home that he needed to do and some that he wanted to do. Working on the projects helped take his mind off what had happened. Dave mentions he was given a severance for about 3 months and wanted to find a new role within that time period if possible. But if he could not find something in that time period, it would not be the end of the world. Dave tells us it was easier to find work when he was laid off than it is currently. Close to the time of this recording, AWS announced job cuts for up to 30,000 people. He made the conscious decision after those first few weeks to spend the first part of the day searching for new jobs and then continued working on different projects in the afternoons. How did Dave know who to reach out to first? Nick argues that most of us likely don’t have a list of who we would call if something like this happened. When Dave came to the New England area, he started working for Dell in tech marketing. Through his work, Dave built a tight bond with many of his co-workers. Dave remembers sending a text message to many of his former co-workers (none of which were still at Dell) asking if they knew of any open opportunities. Dave wanted to understand what former colleagues were working on now and what the culture of their company was like. He started by seeking out people he already enjoyed working with and analyzed whether it made sense to go and work with them again. Was Dave open to different types of roles in his job search, or did that not matter? It had to be interesting work and involve people he wanted to work with or enjoyed working with. Dave says as long as it was something in the tech field, it didn’t matter too much. Dave began his career in systems administration and tech support and had experience in the storage industry, with backups, and with Active Directory to name a few areas. He had also done technical marketing and was open to returning to it. Dave also looked at pre-sales systems engineering or solution architect roles. What about taking roles that moved him deeper into a business unit like product management? Dave says product management is interesting work, but depending on the company, the work may not always have the technical aspects he likes. Many of the product managers at Pure are quite technical, but most of the product management roles he observed at other companies were not as technical as he would like. “It just didn’t interest me. It wasn’t technical enough in nature for me.” – Dave Stevens, on moving into product management It sounds like Dave had done a good job of keeping in touch with people in his professional network over time. “I have always made sure to have a small group of folks that I can just reach out to at any time and…chat about anything…. I’ve always made sure to have that…. I didn’t talk to them all the time, but we all interacted in some way, shape, or form whether it was an e-mail or text messaging…even some stuff on LinkedIn. We all kind of kept in touch…. I had people that I could fall back on and reach out to and get advice from if I needed to. This is the time where I really needed some advice on where to go to next.” – Dave Stevens Dave says he was lucky enough to find a new job before the end of his 3 months of severance pay. Dave’s wife commented that she wasn’t too worried about him. She knew he had a strong professional network. Did anyone in Dave’s professional network ask him what he wanted to do next, or did they just start making recommendations based on what they knew about him? Dave says it was a little bit of both. Some people pointed Dave to specific open roles in the same group where they worked (still in tech, of course), while others directed him to the company job site and offered to act as a referral for him. Dave tells us he’s very willing to give others a referral. “I want to make sure that people that I know and I like to work with come to work with me.” – Dave Stevens Dave says he also turned on the Open to Work banner on LinkedIn. While this did result in many recruiters reaching out to Dave, many of the opportunities they contacted him about were not interesting. Dave is hearing from many in our industry that bots are reaching out to people and trying to take advantage of them. His advice is that we need to be guarded in our interactions on LinkedIn as a result to avoid scams. 19:10 – Skills Gaps and Unexpected Positives What kinds of skills gaps did Dave see when seeking new opportunities? For context, this was roughly 2.5 years ago. Dave says at that time, AI wasn’t as helpful as it is today and was not something that was interesting to him. Dave tells us he uses AI heavily today compared to back then. Dave felt confident in the knowledge and skillset he had built through years of industry experience. Ideally, he would land a new role that overlapped those areas, but if a new role required coming up to speed quickly, he would do what was needed. Dave started looking at public cloud and certifications related to Azure and AWS. “Although it was interesting, it wasn’t really what I wanted to do.” – Dave Stevens, on public cloud technologies compared to the technologies with which he was familiar What were some of the unexpected positive outcomes of getting laid off even though it was difficult in the beginning? One positive, according to Dave, is the amount of people in his network he was able to reach out to on LinkedIn. So many people were open to helping. The only negative Dave thinks is maybe not acting quickly enough in starting his job search. “It’s really about building not only your personal network but your professional network. And my professional network really came to my rescue and helped me understand that…it’s not the end of the world. You’re going to make it. You’re going to do fine. But let me know if there’s any way that I can help you in that journey that you’re on right now.” – Dave Stevens Were there any things Dave and his wife had done (conscious or unconscious) to prepare for the layoff event based on market trends? Dave says his wife is very good at managing their home budget, and since they got married, they intentionally build a financial nest egg they could lean on in the event Dave was out of a job. 22:27 – Elements of the Personal and Professional Network What are some of the things Dave is even more intentional about now with his professional network than he was in the past? Dave received some great advice from a co-worker to reach out to one person in his professional network each week. Many times, Dave will do this on LinkedIn or even via text if he has the person’s number. “Keep that personal connection going. As much as AI is taking over, as much as we do a lot of things on Zoom, I’ve learned over my years of working in the industry that there’s nothing better than the face-to-face interaction…. It’s so much more fun and relaxing to just get out of the office or home office…and just sit down with people and keep that personal connection going.” – Dave Stevens Dave mentions he likes to get together with co-workers in the area every now and then, even if they have the same conversation in person that they would have had on Zoom. It’s different and more relaxing. How can younger listeners who may be trying to break into the industry build a professional network when they might not have a deep contact list or large network like someone in the industry for a long time? Nick and Dave talked about this before hitting record and thought it could be helpful to share during our discussion. Dave has a newfound perspective on this from being around his nephews and nieces. The job market is very different today than when Dave first began his career. “Nowadays, resumes just go into a black hole, and you don’t necessarily know if you’re still in the mix for a current job.” – Dave Stevens Dave has encouraged his nephews and nieces to leverage their personal network to build a professional network. He may know someone who knows someone in the field they want to pursue, for example. “There’s no shame or harm in utilizing all your resources…. Utilize your personal network because you don’t have the professional network built up yet to help you get that foot in the door.” – Dave Stevens Young people could even use their parents as a way to broaden their own network. It’s an opportunity to get introduced to others. Dave uses the example of a chance meeting at a concert that could result in a new connection for someone. Nick would encourage younger listeners to get out to in-person meetup groups on any interesting topic. Go ask people what they are learning, why they work where they work, how they got there, and see if they have advice for you. Dave agrees and has leveraged both local professional groups and meetup groups in the New Hampshire area to meet new people. This is expanding your local professional network as Dave calls it (not to be confused with your global professional network) and is a great thing to do when you move to a new place. You never know when a conversation at a local meetup might help you get a warm lead on a job that will be posted soon. Did the layoff come up in interviews at all? How did Dave handle that? Dave says some people brought it up. In other cases, he brought it up in conversation, wanting people to know he was not let go for doing something wrong. 28:22 – Reaching Closure and Reflecting Back on the Lessons How did Dave know he had reached closure on the layoff situation? Dave thinks he was motivated to take action toward finding a job due to a fear of boredom. He had been working on various projects but knew he would run out of them at some point. Dave had enough time to adjust to not having a job, and he was ready to begin doing some kind of work again. “I didn’t want to get bored. I hate being bored. I hate being bored at work. I hate being bored in general. That’s really what the impetus was for me to go out and start looking…that fear of relaxing for too long and being bored.” – Dave Stevens At this point Dave reached further into his professional network beyond that first group of friends and former colleagues he mentioned earlier. Does taking action in a direction mean we’re ready to move on from what happened? Is it when we have to discuss what happened in an interview, or is it something else? How do we measure this? Dave says it was easier to accept and felt mostly behind him when he was actively looking for a new position. He knew only he could take the actions to move forward. The feeling of what happened before went completely away when Dave accepted a new job at Pure. Dave feels he was very lucky to find a role. Lining up multiple interviews gave Dave momentum and a feeling of positivity. “I feel that people understand that I have the skills for these jobs. Otherwise, I wouldn’t have gotten 5 job interviews as quickly after I really started taking action to look for a job. So, I got lucky.” – Dave Stevens If Dave had to do it all again, what would he do differently? Dave feels he has about 10 more years left working in the tech industry. For now, Dave enjoys the job he has, wants to excel doing it, and wants to continue growing. Dave currently works for the best boss he’s had to date. “He not only pushes me, but he pushes our entire team to just get better….” – Dave Stevens, on his current manager Dave tells us he does not want to be a people manager or a product manager. “I want to continue to excel and expand my depth of knowledge across the virtualization industry and the storage industry.” – Dave Stevens The work at Pure is very interesting to Dave, which is also motivating him to continue learning and excelling. Part of this is using more AI-focused tooling as it becomes available to use. What does Dave think the role of AI tools is in helping with one’s job search? There are a number of tools out there we can leverage to analyze our resume. Dave suggests keeping track of which tool we’ve used to analyze our resume because that could be used to train a model. In addition to this, use AI to research companies. Use them to help you understand what companies are like and what their culture is like. Many people in a sales role within Pure, for example, use an AI tool of some kind to learn more about their customers. Nick reiterates the nuances of acquisitions. Dave worked for a company that was acquired by another company. Over time there was a pattern of people from the company which was acquired being laid off. Perhaps this is a sign we should watch for and prepare. Dave says we need to be looking at and listening for the signs coming toward us. He listens to his wife more intently when she makes a suggestion. Dave continues to check in with people in his professional network and offers advice when they need it. Dave would encourage all of us to use our personal and professional network if we end up in the situation he was in (experiencing a layoff). “Not everybody is going to be able to help you or is willing to reach out and help you, but when someone does…don’t just brush it aside as they want something out of this. They probably genuinely want to help you. So, take advantage….” – Dave Stevens If you want to follow up with Dave on this conversation, Connect with Dave on LinkedIn Check out Dave’s blog site Mentioned in the Outro The three week period Dave took to work on projects may have been what gave him the clarity on the type of work he did and did not want to do once he began his search. Dave mentions getting some great advice from his wife and her emphasis on him pursuing roles that would make him happy and be enjoyable work. This echoes something similar to what Brad Christian shared in Episode 264 – Back to Basics: Technology Bets and Industry Relationships with Brad Christian (2/2) when it came to choosing what to do next after a layoff. If you enjoyed this format and want to hear other stories of people recounting their layoff experience, check out these episodes featuring Jason Gass. He talks about the lost art of supporting others in episode 343, which aligns very well with Dave’s advice on building our personal and professional network. Episode 342 – Planting Seeds: Networking and Maneuvering Unexpected Job Loss with Jason Gass (1/2) Episode 343 – The Lost Art: Marketplace Heartbeat and Finding Closure after a Layoff with Jason Gass (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

How can we help recruiters advocate for us in a tough job market? According to people industry veteran Christy Honeycutt, our guest in episode 353, it starts with being kind and translating your experience into something a recruiter can understand. And even more importantly, it takes practice. In part 2 of our discussion with Christy, she translates deep experience in talent acquisition and recruitment that gives us insight into the current job market. You’ll hear more details about the nuances of RPOs (recruitment process outsourcers), the difference between job hugging and job abandonment, and the importance of personal branding and differentiation. Stay until the end when Christy shares her reasons for turning down C-suite positions and how clarity on her long-term goals is carrying her forward into what’s next. Now that you’ve heard someone model it for you, how will you translate your own experience? If you missed part 1 of our discussion with Christy, check out Episode 352 – People First: Systematizing Go-to-Market for Your Role with Christy Honeycutt (1/2). Original Recording Date: 09-30-2025 Topics – A Deeper Look at Recruitment Process Outsourcing (RPO), Translating Your Experience with 3 Wins, Bad Actors and Leadership in the People Industry, Today’s Job Market and Life Outside the C-Suite 2:56 – A Deeper Look at Recruitment Process Outsourcing (RPO) When it comes to RPO (recruitment process outsourcing), is this a one-size-fits-all approach, or does it show up differently depending on what a company needs? In Christy’s experience, most RPO organizations offer services like executive search, but they may offer full RPO, which usually involves hiring more than 500 people per year. Normally an RPO brings a mix of skills to the table. A client may want the RPO to take only talent acquisition or may want to control offer management, but they may want the RPO to take everything (attracting new talent, offer management, coordinating with HR for new employee onboarding). “If a company wants it a certain way, they can stop it at a certain point…. But most RPOs, full RPOs, is attraction to offer accepted and then it tees over to the HR team.” – Christy Honeycutt John has worked for companies where the recruitment or talent acquisition personnel were marked as contractors in the internal global address book but had company e-mail addresses. Would this mean the personnel are contracting directly with a company or working through an RPO? Christy says it could be either scenario. When she managed an RPO earlier in her career, they were most successful when the client encouraged the RPO to brand as the company. Someone might indicate they do recruitment for a specific company on LinkedIn but be an employee of an RPO. Christy tells us how important it is for the RPO to understand an organization’s mission, vision, benefits, and culture because the RPO is often attracting talent and selling people on why they should apply and interview. “When you think about recruitment and talent acquisition, regardless, it’s a lot of marketing because you’ve got a really cool position and you’ve got to find the perfect fit.” – Christy Honeycutt 5:55 – Translating Your Experience with 3 Wins Right now, recruiters and talent acquisition professionals have a distinct challenge. Many resumes look the same because candidates are using AI tools. “What people think is helping set them apart is actually making them look more similar. So now you’ve got recruiters and talent acquisition; they don’t know if these are fake resumes. They don’t know if they’re real. And they’re getting on the call with these people and finding out they are fake; they don’t have any of this requirement.” – Christy Honeycutt Christy shares a little secret about learning recruitment. She gives the example of a recruiter needing to recruit for an executive level role in technology. Recruiters are encouraged to seek out and find the C-players to practice asking them questions, understand nuance, and grasp the terminology. This is a training exercise. Following this process, a recruiter would then have more credibility once they speak to the A-players they actually want to hire. “What I would encourage is if you are a C-player, you’re not going to know it. Just be kind and know that the person you’re talking to has never held a technical role (probably, most likely)…and might not understand half the stuff that you guys do. The acronyms aren’t going to be the same. Just be gracious with them because the more you can help them translate your experience, the better you’re going to be positioned to get you over the line…. They don’t want to talk to 10 people to get 1 hire. They want to talk to 3 people to get a hire…. And remember that the TA, HR, recruiters, whatever you want to call them…there’s a pretty good chance that they want to help you and that they’re doing the job because they like people. And I think they get a bad rap.” – Christy Honeycutt Christy tells us about something called a slate (a group of 3-5 individuals who apply for a job that a recruiter will go and interview). Recruiters are using AI to help filter through applications. “The biggest thing I can tell you is be your own person. Be your own, authentic person. Have your stories of how you’ve shown up and shown out…. I tell everybody for every job that you’ve worked at, you need to have 3 wins…. Figure out…your top things that you accomplished at each role and have that and be ready to speak to it. And then…ask questions. Interview them too…. Make sure it’s a culture fit for you.” – Christy Honeycutt Christy says things like the great resignation and quiet quitting are just behaviors that get repeated over time. Right now, there is a fearful state of job hugging. “We’re job hugging. No one is hugging a job. People are trying to stay employed in the market. That’s all it is.” – Christy Honeycutt Christy says if you are staying somewhere because you have a job and are not happy, figure out how to make yourself happy by determining it is not a fit, understanding your passions, and beginning your exit plan. “Companies are not our families. They are going to let us go. It’s going to come down to the business.” – Christy Honeycutt It’s important to keep the human element in mind if we are seeking a new role (the human element on both sides). Christy tells the story of a senior recruiter who called her about a conversation with a job candidate, and Christy knew the person was burned out, bored, and curious. “High performers are always open minded and curious, but if you fall in that category, figure it out sooner than later so you’re not burning yourself out because then you’re in a very dangerous situation. That job hugging is going to be job abandonment. You’re going to get to boot. It’s not going to be the other way around. It’s just kind of level setting with your psyche.” – Christy Honeycutt 11:28 – Bad Actors and Leadership in the People Industry Going back to recruiters getting practice and experience from interviewing candidates, Nick looks at this from the lens that everyone needs at bats to gain experience. Though it may be batting practice for a recruiter, it is also practice for the candidate. We don’t practice interviewing very often. Christy agrees it is practice on both sides and emphasizes that kindness is key. She’s had multiple conversations with recruiters who didn’t understand why a hiring manager did not want a specific candidate. We might never know all the effort a recruiter put into promoting us with a hiring manager. Some recruiters, however, should not be in their roles. Christy tells us about a time in her career when she was referred to as “The Kraken.” Christy managed a tight team of talent acquisition professionals who respected and loved her as a boss. They knew she had high expectations of her team. Christy’s team members would have to launch programs for global clients within 30-60 days sometimes, for example. “So, my team had to be kind of like special ops because we managed the globe, and it was high pressure.” – Christy Honeycutt As she progressed in her career, Christy would be given individuals who were not performing on other teams. Before managing someone out of the business, Christy always gave people a chance to redeem themselves because until she met the person and they worked for her, she was only hearing one side of the story. Christy recounts being asked to join an RPO to clean it up. She met with each recruiter to understand the key metrics and performance indicators. Christy tells us that for any job opening (or job requisition) a recruiter was carrying at this time, they should be submitting 3-5 candidates for each job, and a manager would expect this within 2 weeks of the job opening. There was a specific recruiter who only submitted 2 candidates per week across 15 job openings, and Christy recounts the performance conversation with this person. “There are some people that are in roles that they shouldn’t be that take advantage and kind of sit back….” – Christy Honeycutt As people gain seniority in talent acquisition and recruitment, sometimes you deal with people’s egos. This is the exception and not the rule. John mentions it would probably be difficult to coast based on one’s reputation in talent acquisition. Based on the metrics for success and open job requisitions, it should be obvious who is doing well and who isn’t. Christy says this goes back to leadership. Maybe these individuals never had a boss who would hold them accountable. “If we go back to managers and leaders, most of them aren’t trained, and a lot of them want to be liked.” – Christy Honeycutt Christy is the daughter of a Marine. This means the mission gets accomplished no matter what with the fewest amount of casualties. It’s her job as the leader of a team to keep them focused on the mission and accomplishing it. Removing someone from the team may be the best option to keep the rest of the team on track in accomplishing a mission. “You’re only as strong as your weakest link, so if your weakest link is not holding themselves accountable and respecting their team, then they’re putting everybody else’s jobs at risk. And unfortunately, there are bad actors in every industry, in every role, in every organization…and we’ve all seen them. They are like cancer. They really hurt retention. They hurt elevation. They are usually the ones taking credit, taking too long at lunch, whatever the case may be…we’ve all seen them…. It all comes down to behaviors.” – Christy Honeycutt Christy thinks leaders want to be liked and are afraid of having a complaint filed against them. For example, people might file a complaint because they were not doing their job and their manager held them accountable for not doing it. “It’s weird to be in the people industry for so long because it’s just behaviors. It’s just humans.” – Christy Honeycutt Before someone shows up for work, we have no idea what may be going on in their life outside work. Christy encourages us to meet one another with more grace. “Those of you out there, if you’re lucky enough to have a job and be employed, do the job. Because there’s a lot of people that don’t that will come in and do a better job than you. Honor yourself, honor your employer, and show up. But unfortunately, there’s bad actors.” – Christy Honeycutt John directs the conversation back to hiring cycles. He has heard it’s beneficial to apply for a job opening quickly and to be in the first wave of candidates but didn’t really think about the why behind it. Christy tells us this varies based on the position, the job requirements, location, salary, and other factors. In fact, recruiters often have to reset unrealistic expectations from hiring managers (i.e. what a specific role salary should be). “If you think about a client and them opening a position, they probably needed that position 30 days before it was ever approved. So, there’s already a ticking time on the recruiter whether that’s fair or not because in the manager’s mind that role opened the second they thought they needed it. Not when they requested it, not when it got approved, but when they realized in their brain, ‘I need this position filled,’ that’s when the clock starts for them. So, it’s an unfair disadvantage for a recruiter.” – Christy Honeycutt Listen to Christy’s description of a best-in-class 4-week process from job opening to making the right candidate an offer. 20:45 – Today’s Job Market and Life Outside the C-Suite If we look at this through the lens of the current job market, how much do recruiters need to sell candidates on roles when there are hundreds of applications to sort through for a single job opening? “Tech is like recruitment, like marketing. It’s always the first to go…until they realize…it went, and we need it. So, it’s a boomerang effect with those industries…always has been, always will be.” – Christy Honeycutt Christy tells the story of being at the HR Tech conference with a young lady who was recently laid off from a tech company. This person walked from booth to booth and began networking with people in search of new roles and was able to leverage Christy to get some introductions. She had 5 interviews over the course of the 3-day event. “In the job market today, with recruiters not able to tell if it’s an AI resume or not, with them being overloaded with a vast amount of resumes…the best thing that anybody can do is make sure that your personal brand is on point. Make sure that whatever it is that you’re doing…you’re sharing, you’re engaging your community, and that you’re seen doing it.” – Christy Honeycutt Christy was part of the same tech startup mentioned above and also lost her job. But she had been working on her personal brand before that happened. Christy was speaking at events, sharing with her community, doing podcasts, and doing many go-to-market things on behalf of her employer. Christy’s heart goes out to others in her field who have been out of work for multiple years. Within 3 days of losing her role, Christy was offered 3 different C-suite positions. She turned them all down. “I’ve had that moment where I’ve realized that where I want to go and where I am are 2 different places…. If I put my focus on something, my energy is going to flow in that direction, and I need to make sure that’s the direction I want to go…. Do I want to go be c-suite and kill myself for the next 4 years? …But the reason that gave me confidence is I’m 3 days without a job. I’ve got several job offers. And I realized, they don’t care how I work with them. They just want to work with me, so why don’t I go out on my own?” – Christy Honeycutt, on the internal discussions she’s having after encountering job loss Christy understands she’s in a gifted place only because she put in the work of giving back to her community before she was in a tough spot. Her efforts include things like hosting Inside the C-Suite and doing free mentoring and coaching for others. “It’s because of all the goodwill I’ve done. My community paid it back tenfold. So set yourself apart in whatever it is that you’re doing…. Where we are today is you have to have a differentiator, or you’re going to be sitting on the shelf for 5 years.” – Christy Honeycutt Christy mentioned previously that it’s lonely when someone takes a C-suite role. How did her conversations with executives on Inside the C-Suite together with her experience in talent acquisition and recruitment impact her decision to not take a C-suite role? Christy knows that she doesn’t do anything halfway. If she were to take a C-suite role, she would be working 80 hours per week and traveling nonstop. Christy and her partner want to slow the pace down for their family, take time to travel, and do more purposeful things. She shares a story about Matthew McConaughey wanting to make the shift from romantic comedies to more serous roles to illustrate a shift of priority and focus. “Yeah, it crossed my mind. But it does not align with my long-term goal…. I realized I have a choice. You know, the universe has brought a lot of stuff to me. Is it because it’s meant for me, or is it noise?” – Christy Honeycutt Christy has shown up, given to her community in a visible way, and found her voice. But taking a C-suite role right now is not where she wants to be. Some of the job offers Christy received came from people who had been on her podcast. Christy tells more of the story of being at HR Tech and the reactions people in the industry had to her being on the market. Christy plans to continue conversations with those people about ways they can work together moving forward. “I’m really good at certain things, which you guys have broken down and helped me understand. I repeatedly get asked for those things, and those are the things I like to do. So why not go do that? Why not go be a consultant and do the things that I really like to do for people and not do the things I don’t like to do…? …I can just go do the fun stuff that they need my specialization in.” – Christy Honeycutt Christy wants to stay true to herself and honor the decision to increase bandwidth for her family. Many of the C-level executives Christy speaks to on her podcast love what they do, but they’ve had to learn to put themselves first. “I hear this more often than not. When they first start their organization, it’s business business business. Their health fails. Their family fails. So, the ones that actually made it and recovered through that little spike and actually make it out on the other side very quickly flip to ‘take care of my body (my temple), my soul, my family, then my business. It’s a battle for them.” – Christy Honeycutt At the time of this recording, Christy is thinking of starting her own firm, so she hopes she can take it slow enough to avoid these pitfalls. When we decide to slow the pace and do more of what we enjoy, can reflecting on those 3 wins from each previous job help us be confident that we can still get those wins without running at a hectic pace? Did Christy do this when thinking about what she wanted to do? Christy says she did not think about these for herself even though it would be her coaching to others in need of advice. “What I found interesting is that when you’re looking for an answer, if you actually open your eyes, it’s right there. It plays back to you. It plays back to you in conversations you have with people…. You often say what you need and what you want and where you’re at, but you don’t comprehend it. But if you hear someone you love, that you trust, repeat it back to you…it’s almost like it gives you permission to accept it.” – Christy Honeycutt Sometimes instead of giving people advice, we need to act as a mirror and reflect back what they’ve said. Christy didn’t need a C-level title. She doesn’t need to go do something to prove she can do it. She’s already done it. Christy understood she was ready for something different, even if it’s a little bit scary to consider going out on one’s own. “It’s scary to put yourself out there like that, but if you don’t, you’ll never know. I’d rather try and fail and learn than regret and not know.” – Christy Honeycutt If you want to follow up with Christy on this conversation, you can find here: On LinkedIn On her website On the podcasts she hosts – Inside the C-Suite and StrategicShift Mentioned in the Outro Do you have 3 wins from each job or at least the past several jobs you’ve held? And do you know the stories that go along with these? There are prerequisites that must be met before we can speak to our wins in an interview. It starts with documenting our accomplishments on a regular basis. Consider what the 3 wins are from your accomplishment list. Maybe you have more than 3 or need to use a different set of 3 based on a job to which you’re applying. Consider writing the story that goes with each win. It could be a resume bullet, but think of it as more detailed and something you can share in an interview. This is part of drafting a career narrative like Jason Belk suggested in Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2). We should not only write the draft but gain practice sharing the stories verbally in interviews, possibly conversations with our manager, and maybe even in conversations with industry peers at networking events (if and when appropriate). This is an iterative process! We like looking at conversations with recruiters as opportunities to practice telling our win stories. In the discussion with Christy, we heard about her experience losing a job. In Christy’s case she had been giving to her network long before this happened in a very visible way. Maybe you are doing this in a less visible way. Consider documenting that work, but make the overall intent to help others and impact people positively. It will pay off later when you need help. Christy shared an exercise in finding clarity. She knew a C-suite role would not match the pace that was aligned with what her family wanted. It wasn’t just about personal ambition. Remember to check out Christy’s podcasts, Inside the C-Suite and StrategicShift. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Go-to-market strategy is something we often associate with a company or its products / services, but what if we could apply go-to-market to our job role? Christy Honeycutt, a talent acquisition veteran and our guest this week in episode 352, has used this mindset as a personal differentiator starting with her first job in the banking industry. We’ll follow Christy as she describes early experience as a people manager, learn why she developed a people first mentality, and recount the events that kickstarted her career in recruitment. This story helps us understand what is required to systematize the work we do and how difficult it can be for things that seem easy. Christy will also educate you on the importance of developing AI competence and the impact of recruitment process outsourcing on job candidate experience. Original Recording Date: 09-30-2025 Topics – Meet Christy Honeycutt, A Go-to-Market Perspective, Beginnings in the Banking Industry, Learning to Systematize and Duplicate Yourself, A People First Approach, Getting into Recruitment 2:10 – Meet Christy Honeycutt Christy Honeycutt has 20 years of talent acquisition experience, go-to-market experience, and some marketing experience sprinkled throughout. Christy is also the host of two different podcasts: On Inside the C-Suite, Christy interviews executive leaders to gain insight from life in these roles. StrategicShift is focused on the future of work, innovation, and AI. 3:17 – A Go-to-Market Perspective How would Christy define talent acquisition and recruitment and the differences between them? Recruitment should be thought about as more active. There is a job open with specific requirements which need to be filled based on time constraints. Talent acquisition is more strategic according to Christy. This would include understanding why a role is vacant, the succession plans, cultural initiatives, and workforce planning. Christy refers to this as “engaging passive pipelines for long-term goals.” Personnel in talent acquisition and recruitment are usually in those roles because they want to help people, but these roles may look slightly different across companies of various sizes and in different industries. How would Christy define go-to-market? We hear this term quite often but are not confident that everyone truly understands what this means. For context, Christy talks about looking at this with a lens across many different departments / internal organizations – marketing, recruitment, and even sales. “Go-to-market is understanding what is the product and who is the end user…. Am I filling a job? Then I’m going to market for that candidate that fits that job. Am I working for a tech company (which I most recently did)? Then, yes, I need to understand what is our product, who is the end user, who is the buyer…and how can I get this to market for them…to see, to use to buy, and to be delighted in? The go-to-market is really kind of a Frankenstein effect in my opinion. It’s really understanding the value and how it translates and then how you can connect the dots…. Go-to-market for me has just kind of been at my core since I was a kid.” – Christy Honeycutt For recruitment, the go-to-market is usually set based on an organization’s vision, mission, values, and culture. Christy uses the example of negotiating with her father (a former Marine) to get what she wanted when she was younger to illustrate that go-to-market can mean understanding how to sell. 7:01 – Beginnings in the Banking Industry Christy was a cheerleader in high school and got a fully paid scholarship to college, but at age 17, she was diagnosed with cancer. As a result of the diagnosis, she was not able to attend college. Christy always wanted to be a mom and did not want to ruin her chance to have children. Christy married her college sweetheart and became a stay-at-home mom of 2 children. She is now heathy, happy, and thankful she was able to have children. Christy’s father owned a nonprofit, and even while she was a stay-at-home mom, Christy was involved in marketing for nonprofits as a result. Christy also was part of the boards of her children’s schools, did volunteer work, and even taught pre-school. After moving to a new state, Christy needed to get a job to support her children. After applying at a bank, she landed a manager job. Within 6 months, the bank branch where she worked was the highest producing in the state of Texas. Christy came up with marketing initiatives to get customers to visit the bank. She gives the example of a yearly Halloween contest. At one point, the bank was robbed, and Christy learned to lead in stressful situations through this experience. She also learned that she has a photographic memory. Christy tells us her career really began in banking and then transitioned into marketing. Listen to the story about one of her clients who was a mortgage broker. Christy had 2 boys in various sports and was wearing herself out between work at the bank and home life. This mortgage broker sent an e-mail to help Christy get interviews for a role at a different bank. Christy tells the story of interviewing in the mortgage division of another bank (Prime Lending) close to Halloween. She was dressed as Lucille Ball for an event at her employer and ended up going to the interview in costume. The people who interviewed Christy loved it, and she was offered the job on the spot. 11:40 – Learning to Systematize and Duplicate Yourself “But the really interesting thing that happened is they said, ‘we want you to hire 3 of you…. What you’re doing is working, so what we’d like you to do is go have a think about how you can multiply that into other branches….’ Can you imagine sitting down and going, ‘what is it that I did today and how did I do it?’ …And, just really creating a job description, a profile, how they’re going to be successful…and then find the people and train the people? So that was my very first…experience with recruitment.” – Christy Honeycutt After removing the shock of being told to multiply herself, Christy began a process that she would repeat over and over in her career – thinking outside the box to create something special that she could automate or systematize. At that first bank, Christy managed people but had no prior training as a manager. How did she figure out how to manage people, and then how did that translate to the role in which she was asked to create job descriptions and multiply herself? We’ve heard from some guests that most first-time managers do not get training. Christy echoes this sentiment. Large banks will train you on laws and procedures, but Christy tells us she had to train herself on the people side. Mainly, she needed to learn how to manage the people, their schedules, and learn how to encourage them. Despite being the boss, Christy was still friends with the people who worked there. In being asked to multiply herself, Christy had to systematize the job she was already doing. She tells us it was a daunting task. “When you’re really good at things, what I’ve found is they seem natural to you, and they are not that hard.” – Christy Honeycutt When asked to duplicate herself, Christy downplayed her contributions a little bit. She advises all of us to step back and really think about the work we have done because we might not immediately recognize it and may downplay it in a similar way. As humans, we might at first feel like it is bragging to share the factual things we have done. Christy had to think about what she did, simplify it, and figure out how to translate that to the people she needed to hire. Christy was working for the mortgage division at a bank, and they needed to get more loans. She first sought to understand the sentiment of the bank’s customer base and if they had any needs. Step 1 was hosting a customer appreciation event. The customer appreciation event generated direct feedback on the bank’s processes and product offerings. Next, Christy sought to understand the bank’s target market, which was real estate agents. She thought about how to get real estate agents to use this specific mortgage broker. New real estate agents need help with marketing, so Christy got certified and began teaching marketing classes to real estate agents. All of the agents would eventually begin using the bank. “It’s just kind of understanding what’s in it for someone else…. I just…went step by step by step and built the framework….” – Christy Honeycutt The framework Christy mentions above outlined where the opportunities were for the bank (i.e. who might need their services), allowed for dividing up the work across divisions, and provided insight into the key performance indicators (KPIs) for measuring success. In many ways, Christy acted as a liaison between the bank, the real estate agents, and end customers. When seeking to hire people to do the work, Christy looked for empathetic people who were interested in helping others. Another avenue for the bank to increase the number of loans was working with first-time home buyers who might have poor credit. This would help real estate agents who needed home buyers. The bank started doing credit repair seminars to generate new leads. “I was bringing in buyers, delighting previous buyers, and then also going after the vendors that would help participate. Honestly, that model…has kind of been my two step my whole career.” – Christy Honeycutt Nick thinks Christy’s process is actually a three-step with the third being supplementing the above with the type of education which will both Christy and the audience she seeks to serve. Nick thinks this pattern will probably be repeated somewhere in her story as well. Christy says it actually does repeat. She recounts getting an AI-focused certification when this technology wave started catching on. “In the next 12-18 months, over 80% of all organizations globally will have adopted AI if they haven’t already. So, if you’re looking for a job, and you don’t understand the basics…AI has a lot of different names. I want you guys to think about that. That’s usually marketing.” – Christy Honeycutt Christy tells us AI agents are mostly marketing and an attempt to make things more consumable and understandable rather than some flashy new invention. Christy recounts talking to executive leaders who have mentioned having AI in one’s toolkit even as a kid is important to be relevant in the future workforce. All of us need to have more than a bare minimum exposure to ChatGPT, for example. We need to play, create, and tinker with AI tooling to develop a point of view that is uniquely ours. Christy feels AI will take jobs but that they will be lower-level things that we probably wanted automated anyway. She gives the example of a communications outage impacting airports in Dallas / Fort Worth and the decision to go get information from an AI agent on the company website rather than call the help desk. For any job you go into, expect to get questions around AI. Christy mentions a recent visit to the HR Tech conference. Every booth was promoting some kind of AI, and Christy shared with executives at the conference that buyers don’t fully understand the difference between products because “everyone is saying the same thing.” Christy reminds us there are ways to get low cost or even free education on the topic of AI so we can develop competence and a point of view. Nick shares his perspective on what he calls the “double check mark,” which is looking to educate yourself or build skills in an area that can help you both at your current employer but also make you marketable and relevant in the greater job market. Something that only helps you with your current role isn’t quite as attractive as something that can help you later as well. Ideally, you span into both categories, but it is not always possible. Christy mentions this is a very tech answer and gives the example of making a suggestion to an executive leader while advising for a tech startup. She only brought suggestions that would be attractive to / helpful to many customers (not just a single customer). When Christy did research on what was impacting customer sentiment and spoke about understanding product market fit, was that all natural at the time she did it while working at the bank? Christy says it was natural at the time. As a single mom, she needed to be scrappy. “It’s funny because as I sit back and I think…I realize everything was kind of predestined. And at the moment it just felt like I was reacting and I was doing it, but…as I do my own reflection, I’m realizing that these cycles I’ve been on have always been for a reason, guiding me to where I’m at.” – Christy Honeycutt Reflection is one way to uncover our strengths, and Christy reminds us that just because something is easy for us does not disqualify it from being a strength. John mentions that performing a skill really well is different than being able to teach other people how to do it. When something comes easily to you, it might be difficult to know how to teach someone else to do it. But it sounds like Christy had to learn how to systematize the things she did so she could train others (i.e. it was not natural). Christy says it definitely was not natural. She remembers how she felt when asked to duplicate herself. It seemed like a crazy request at the time. One thing that really helped Christy through this process was looking at job descriptions for roles similar to hers at other companies and analyzing both similarities and differences. “Everything is a learning lesson. I don’t regret any place I’ve ever worked. I don’t regret any situation I’ve ever had because it was all opportunity for me to learn how to manage through a situation (good, bad, or indifferent) and reflect on it and how I would do it differently.” – Christy Honeycutt Christy mentioned earlier that no one learns how to be a manager. She is a forthcoming author and was recently signed with Postal Publishing House, and the book will be about leadership. In the book Christy talks about how no one is trained to be a leader and how people often just kind of fall into it. She feels it is a big gap. Even as people get up to the director level and maybe even the VP level, they are still learning. “No one sits you down and says, ‘hey, these really crazy things are going to happen, and you’re going to have to respond to these humans in a particular way. And by the way, you’re human, and you might have a really bad response to what you have to respond to….’ There’s lots of things that you deal with that I don’t think anyone could prepare you to deal with. And so, you learn on the job.” – Christy Honeycutt Did the need to create job descriptions and hire people to multiply herself make Christy enjoy management more or question whether she wanted to keep doing it? Christy tells us she questioned whether she wanted to keep doing it. Her responsibilities ended up expanding well beyond the go-to-market work she was doing, and things became more complex. Christy went from being in charge of 1 person to being in charge of 4 people trying to do everything using her methodology but with their own flair. “Frankly, I got kind of bored because I created something, I duplicated myself, multiplied myself…. Ok, I’m ready for the next thing. I can do this, and I’m ready for the next thing…. I’m constantly curious, and I always need something more just to kind of keep my attention. There’s a lot of people in the industry I think are that way, especially in tech…. And those are the people that employers are looking for. They are looking for the curious people. They are looking for the open-minded individuals that want to adapt and want to learn and do more because those are the ones that have the longevity.” – Christy Honeycutt Once we master things as technical people, we often want to move onto what is next (something new to learn, a new certification to chase, etc.). 26:23 – A People First Approach Did Christy’s background in cheerleading help her in marketing? Actually, yes. Christy gives the illustration of high school cheerleading and pep squads. These are made up of people who love community and love to empower and cheer on other people. Christy reminds us that cheerleading is a sport. For those in cheer or pep squad, it’s not about wearing cute outfits. There is a commonality among the people who participate: an enjoyment of collaboration, a desire to win, and a belief that there is power in the energy they are giving. Christy likes to look at things from an energy lens. “In every industry you’ve got really good players, and you’ve got bad actors. So not all recruiters, not all talent acquisition people are really kindhearted, love what they are doing, and in it for you…. But the majority of the people in the HR and TA (talent acquisition) space generally joined that type of work because they love people, and they are fearful right now because they think AI is taking their job. And some of them it probably will, but you’re never going to get away from the EI and the EQ piece that is required in the age of AI. We need to be more human now than ever.” – Christy Honeycutt Some people in these roles may hate their job. Some may love you as a candidate but be unable to get anything through. At what point did Christy realize that for her it was more about the people? “It’s always been about the people for me. Everything I do has been about people. I’m people first just in everything I do.” – Christy Honeycutt After getting the job where she needed to duplicate herself, Christy wanted to talk to all of the company’s customers as her first task. Christy mentions the concept of go-to-market is the same regardless of the company where we work. “Your customers are your biggest resource because they will either be the loudest complainers or your biggest fans.” – Christy Honeycutt Customers with a positive sentiment toward a company (or its products and services) can offer free insight on how to serve them better. This may come in the form of suggestions for new features and capabilities or advice on overall direction, for example, and provides a perspective that a vendor cannot otherwise see. Christy has been told she is too “client advocate friendly.” When selling a product or service to a customer, if users don’t adopt it, you are only as good as the contract. Christy calls this being a one trick pony. On the other hand, we can sell a product or service and care enough to check in with customers and make pivots to make the product or service more valuable. This creates what Christy refers to as a “client for life.” “And that’s, I think, where my specialty comes from is the human side, the people side. It’s just always remembering what’s in it for somebody else. Because we all have exchanges every day. What’s in it for the other person?” – Christy Honeycutt Christy makes a hypothesis that we do this podcast to help people and because we care, and at some point in our career we probably needed what we are giving. What would you have said is the reason for the podcast based on being a listener? “People are my thing. I get the heart. I get the energy, and I think at the end of the day, we all put our shoes on the same way.” – Christy Honeycutt Christy really enjoys hosting Inside the C-Suite because it demystifies what it is like to be an executive leader. “It’s understanding how you navigate and how your priorities change…what’s now, what’s next, what’s urgent always evolves as you grow in your career.” – Christy Honeycutt 31:52 – Getting into Recruitment How did Christy end up getting into talent acquisition and recruitment? Even with her hectic travel schedule hosting events for her employer, Christy never missed a little league baseball game in which her kids were playing. At a specific game, someone asked Christy what she did for a living and if she had ever thought about working in recruitment. The person who made the suggestion helped Christy see the similarities between recruitment and marketing. “Client needs a certain thing, and you go find the certain thing. And however you find it, you find it. That’s a lot like marketing. Exactly.” – Christy Honeycutt, describing an exchange with someone who encouraged her to pursue work as a recruiter Christy went to an interview for a recruiting role and got the job on the spot. The company was bought out by Kenexa(CEO was Rudy Karsan) which was later acquired by IBM (or “big blue” as Christy calls them). Christy did recruitment process outsourcing for this company (or RPO for short) and specialized in this area for many years. She led this at IBM and later at Korn Ferry. She tells us there are so many layers to recruiting that people don’t know. Staffing agencies, for example, often get a bad reputation. These agencies are predominantly focused on high-volume hourly roles or other short-term positions. Quality and candidate experience are not always the best. These recruiters have to move quickly because a successful placement is how they get paid. “And when you do that really, really well the clients think that you’re their internal recruiter…. I think over my career, not me directly but within my teams, I’ve probably placed around 30,000 individuals.” – Christy Honeycutt, on specializing in RPO Listen to Christy talk through an example of mapping through the workforce strategy for a client that wanted to outsource global recruitment on a tight timeline. She emphasizes that when we work with a recruiter, that recruiter might not work for the company where we are interviewing. “When an RPO does a good job, not only does the candidate think that they’re an internal recruiter, but the clients think they are an internal recruiter.” – Christy Honeycutt Christy talks about making a move from being a liaison manager for a client (focused on the client’s technology sales and marketing) to managing an internal team. The client thought she was their employee. Don’t miss the part where Christy mentions she wanted to take a role as a recruiter so she could understand how to be a better manager. “While your…audience is out there looking for jobs, just be mindful that…TA, recruitment, HR…depending on the size of the organization…you may be talking to an agency. You may be talking to an RPO. You may be talking to an internal recruiter. You can ask them. They don’t have to tell you.” – Christy Honeycutt Another challenge for the job seekers out there is the amount of fraud happening. On average, every US citizen has 7 points of fraud directed at them per day. Christy mentions getting multiple text messages from companies claiming to be Randstad, Robert Half, or some other firm about jobs. It’s all fraud. Don’t fall for it! When Christy worked for Korn Ferry and another tech startup, as part of the go-to-market strategy, she created a candidate application analysis tool which informed clients about the candidate’s experience. Some clients didn’t realize, for example, that their site was down and was preventing people from even applying. This tool also informed clients about how they showed up on sites like Glassdoor and what the biggest complaints are. The lowest scores 9 out of 10 times for a company are for leadership. Keep in mind rankings on Glassdoor are from job candidates and people who have worked at a specific company, and most do not take time to write glowing reviews of an employer. “We have to give the employers the benefit of the doubt. So when you know where the sources are coming from and you’re honest with yourself on when you give feedback and how you give feedback…until we can all step up as humans and start giving 2-3 good feedbacks a day, we’re never going to balance out the negative.” – Christy Honeycutt Mentioned in the Outro Christy did a great job emphasizing that we understand what is it for the other people we work with (incentives, metrics, what success looks like for them), and that was part of executing a successful go-to-market strategy in banking and other areas. Here’s how Nick thinks a go-to-market might look for someone working internal IT: Understand the technology landscape at your company (hardware, software, cloud services and subscriptions – the overall vendor landscape) Understand the end user base you support and the capabilities you are providing to them. Think also about the value being delivered through these capabilities to both internal users and external users if applicable. Think about the capabilities you provide like products. Can your products be enhanced based on end user needs and feedback, and are we willing to take the feedback? Christy modeled the importance of understanding customer sentiment that can help us here. Will an enhancement save time, decrease cost, decrease risk, or increase revenue? These are important impact metrics to understand (and document). If you change a hardware / software vendor (i.e. a tooling change), will it disrupt your customer base, or can you still provide the same capabilities? Make sure you understand this! Is there a new capability you could provide that delivers more capability? That’s part of the go-to-market. Are there members of the end user base who need education to get more value from the services and capabilities you’re offering? Don’t forget to check out the podcasts Christy hosts –Inside the C-Suite and StrategicShift. Nick feels podcasts such as Inside the C-Suite are great sources to gain perspective on how executive leaders operate. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

Original Recording Date: 11/2/2025 Expect a Change Moving Forward – The Schedule Hi everyone – thank you for being a listener. This is a brief reminder that episodes from this point forward will be releasing every 2 weeks for the time being. Life circumstances have demanded we make this change to keep producing the show. Don’t expect any changes to our content. We remain committed to serving the technology professional and helping them accelerate career progression, increase job satisfaction, and be more effective in their existing role. Thanks for coming along with us on the journey, and it will continue. Expect to hear from us every 2 weeks from this point. See you next week for another action-packed episode! If you have ideas for a topic we should explore or a guest we need to have on the show, feel free to contact us via any of the channels below. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

What does it mean to become AI native? It’s not about using every AI tool on the market. For Milin Desai, the CEO of Sentry, it’s about becoming familiar with the tools and opting in to use the capabilities that deliver practical value. This mindset was born while Milin was the general manager of a business unit at a software company. In this role, he had to manage a profit and loss statement, learning the art of constrained resource planning and organizational adaptability. In episode 351, our final installment of the conversation, listen as Milin describes both the gravity and different intensity of the CEO’s role compared to past roles. You’ll get insight into the strategy behind enabling an entire organization to shift and become AI native, how this translates into value for customers and employees, and how the individual contributor can be a better contextual communicator when speaking to busy leaders. Stick with us until the end to understand how a set of first principles can guide our career progression if we choose to actively participate in it. Original Recording Date: 09-29-2025 Milin Desai is currently the CEO of Sentry. If you missed parts 1 and 2 of our discussion with Milin, check out Episode 349 – Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3) and Episode 350 – Scope and Upside: The Importance of Contextual Communication with Milin Desai (2/3). Topics – Contrasting the Role of General Manager with CEO, Embrace Practicality with New Technology, Junior Personnel and a Return to First Principles, Shifting Organizational Focus to Becoming AI Native, Contextual Communication to Leaders and Parting Thoughts 2:41 – Contrasting the Role of General Manager with CEO General managers usually own a profit and loss statement (or PNL statement). How was this different than the things Milin had previously gone through? Milin says you do have to prepare yourself for it, and his experience as part of product teams was very helpful to gain familiarity with many of the elements of the general manager role (i.e. revenue protections, investing resources in specific efforts, etc.). Things get very interesting when you are managing PNL in a constrained environment. Milin gives some insight into annual planning and the behaviors he has observed during these times. “Very rarely do people come back and say, ‘I’ve got the same org. I’m going to reshape the org, move things around, and I’m going to do these new things with the same number of people.’ I think most leaders are not very good with that philosophy.” – Milin Desai In this role Milin tells us he learned how to do planning with specific constraints in mind (i.e. stress testing as if no resources / extra people could be added), and this idea of keeping teams lean taught him about the adaptability of an organization. “I really think every organization should do that, and then, you always have the ability to go add more people…. Structurally say, ‘is this how we still want to operate?’ And we rarely do that…. I knew the numbers, the resources, and everything else. We did a lot of planning. But what I learned I needed to get better at is this constrained planning…” – Milin Desai Milin loved working as a general manager and thinking through how to optimize even if the organization didn’t get everything it wanted. “What is the hardest thing to do? To say no. What is the hardest thing for a product manager to do? Shut down a feature. What is the hardest thing for a VP of engineering to do? To shut down a product…. I’m lucky enough to have a leadership team that…thinks along those lines. We are unconstrained, but we kind of try to make sure…let’s put some artificial constraints and see what we would do different.” – Milin Desai Nick mentions this is analogous to the employee who is no longer a fit and having to say no to that person moving on with the company. What is the contrast between being a general manager of a business unit and being the CEO of an entire organization? Milin remembers some of the conversations when he was considering becoming a CEO. “Milin, are you sure you want to do this? And it was not a capability question. It was, ‘do you understand what you are signing up for?’ …It is very different. You are responsible for everything. There is no other person. There is no other excuse. There is no other system I can blame. Something goes wrong at Sentry…I am it. And I have to go to sleep every day thinking about it. I wake up every day thinking about it.” – Milin Desai, quoting a question from former boss John Martin and speaking to the contrast of being CEO compared to general manager You have to know you want to be CEO. Many people think they want to do it until they are doing it and realize how difficult it is. Milin admits being CEO has been difficult, but having a great team has been very helpful. Before taking the role, Milin spoke to his wife about it. He describes the role as “a very different intensity.” Three months into Milin being CEO of Sentry, COVID showed up. That is a challenge he never would have expected. “It’s very different to be a GM versus being a CEO. You’re using your same skills, but it’s a completely different magnitude of responsibility and impact.” – Milin Desai As a general manager of a business unit, Milin could change the trajectory of his business unit. As CEO, mistakes are much more costly. But you cannot do it in fear. In fact, for Milin, the larger impact of his role is exciting. The right partners and team around you as CEO are very important as are taking and applying lessons you previously learned. Milin continues to push himself to improve over time even after reaching the CEO level. 9:22 – Embrace Practicality with New Technology John cites technology waves like virtualization, cloud, mobile, and generative AI. With generative AI, many of us get value from it. But many people are unconvinced of the value and are even fearful it will turn into something like Skynet (a reference from the movie Terminator 2). How does Milin approach people with this mindset? Milin is practical with his approach to technology. “The unconstrained view of what AI could do…we have seen it in movies already. So, I think the unconstrained aspect of this is what we can imagine or maybe even worse…. You can almost think about that and worry and not participate and be on the other side if that happens…. Or, just practically, on a day-to-day basis, figure out what aspects you want to opt in. So, I’m more in that camp…. On the AI front, just think about how it could practically help you on a day-to-day basis versus trying to worry too much about all the aspects, some of which you absolutely don’t even control…. I think it will bring productivity in ways that we don’t even know.” – Milin Desai For example, Milin doesn’t have a voice assistant, didn’t find them useful, and did not opt in. If you’re worried about supporting a bigger cause, Milin tells us that bigger cause is going to happen irrespective of us supporting it. Instead, we should think about how to practically use AI tools and become an active voice in it. Milin tells us his wife just started using ChatGPT and loves it. He asked her the value question on whether it was worth paying for it vs. staying on the free tier after she talked about how much it helped. She agreed that it was worth the money. Milin cites the potential for productivity gains we don’t even know or understand yet. For example, imagine a robot doing laundry for you so you can do something else. Milin thinks there will be some significant value points with robotics and AI. He’s excited at the potential for optimizing daily tasks that this could bring. “Just be practical in how you’re using it and how it will bring value to your life, and the ones that you don’t find valuable, don’t do it. I don’t try every AI tool…. But the things I care about, I lean in.” – Milin Desai We don’t control the unconstrained and should not worry about it according to Milin, but we can be a positive participant in this (AI) by participating in communities that serve the greater good in this area. Milin says the idea of an AI bubble bursting will be determined over time, but transformation is happening. There are business use cases in vertical industries for AI (i.e. for medical transcribing). It’s not just people doing personal research at home, for example. The intersection of AI and robots will be an exceptional thing. We have to figure out our place in all of this, which is a harder question. “I fundamentally believe you will still need engineers. You will still need certain things. But certain functions are getting automated…. You’re going to have to figure out where is the new value being created and how…you participate in the new value system.” – Milin Desai This comes back to curiosity, asking good questions, listening, watching for where things are moving, etc. We can apply those same principles to the field of AI. Milin tells us almost every company out there is willing to let you explore and learn when it comes to AI (which means. At Sentry, people are encouraged to use the tools they want to become “AI native.” “Leverage that. Lean into it. Don’t shy away from it.” – Milin Desai, on utilizing your job role and resources to learn AI tooling and the value it can provide 15:07 – Junior Personnel and a Return to First Principles Nick wonders how junior technology personnel can develop the expertise of someone who is more senior when the senior folks developed their expertise before AI existed? Can giving a junior employee AI tooling help them gain that same level of expertise? Milin says this is about getting more “at bats.” Someone could read all about running a company or working with top leaders, but until they have done it, they cannot really understand what it is like. For senior personnel, using AI tools will remove some of the tedious tasks and be more of an accelerant. Junior personnel do need to become AI native, but in addition to this, Milin recommends spending your time thinking through failure modes and other fundamentals. “If something breaks, will I be able to debug it? What are the failure modes for a user that is accessing the system? At what point in time will we have to look at scale aspects of the system…both just scaling versus architecturally? And then you start asking those questions and putting those pieces as learning building blocks…. I think you have to think again at first level principles, system level thinking.” – Milin Desai In addition to the above questions, think about the following: Is the user’s experience intact? Does good design documentation exist? Milin says these “first principles of system thinking” develop from writing, deep thinking, thinking through things from a user’s perspective, considering failure and scaling modes, etc. “And so you build those habits, even as a young engineer…. When you get to a point, you will start asking the right questions, and AI or no AI, you’re going to be successful and valued because you’re thinking in first principles. You have to develop that, but you can develop that with AI and with the folks around you.” – Milin Desai 17:47 – Shifting Organizational Focus to Becoming AI Native With Milin’s view on AI as not pure hype, how are organizations reorganizing priorities around how products get developed, tested, and shipped? Milin tells us over 150,000 organizations use Sentry from the smallest startups to the largest organizations. The customer base scale is massive, and the feedback is constant, fast, and iterative. “We have basically told the entire company, ‘You must become AI native….’ The number one thing we did was we unconstrained everyone to say, ‘go figure out how to become AI native.’ Whether you’re at Sentry or otherwise, this is a skill you are going to need. So, participate in it.” – Milin Desai Milin says employees were encouraged to initially choose the tools necessary to become AI native, and corporate constraints would come into play a little bit later after personnel had built a skill base. The Sentry team also had a set of people building AI-specific capabilities, but the intention was not to have a single, centralized AI team. “There is a set of people who are experts at fine-tuning…the models and how everything works. But, if you want to be the company of the future, it’s not an AI team. It’s everything in terms of what you’re building has a perspective of participating in an AI native world. It cannot be that…30% of the team that is working on AI stuff, and the others are not….” – Milin Desai AI is a tailwind for Sentry according to Milin. It was a goal to take some of the things the team was already doing (i.e. products they were building) and look for ways to make those products AI native. Milin spoke to some of the work new graduates at Sentry did to build session replay summarization. This was their chance to take a project from 0 to 1. Having an AI-themed “hack week” inside the company created a new energy and air of excitement. “And so where are we right now? We basically are like, ‘what does it mean for Sentry to exploit all the opportunity it is in software?’ …It’s not constrained to a team. It’s organization wide…. Pretty much across the board, every team is going to look at what they do and say, ‘Is it a version that brings the experience forward because we now have LLMs and AI and all this new tech?’ That’s the question you have to answer.” – Milin Desai The individual teams also have to think about where the experience in their product gets enhanced with these new technologies. It might be in the front end, back end, or something invisible to the user entirely. Milin also mentions there is an internal team that owns building the core AI and infrastructure elements separate and apart from their product enhancement focus. While everyone is moving in the same direction now, this shift Milin describes came in phases. It was introduced with a little guidance and happened over a period of 3-4 months. “But you have to bring people along for the ride versus… ‘here’s what you’re going to do.’ That doesn’t work.” – Milin Desai John says at first these steps sound like ways to modernize an organization, but in this case, it’s more to keep up with current trends and new ways to provide value. Milin says it is to stay relevant. “It’s to stay relevant. That’s why I made the statement – with or without Sentry, every employee has to become AI native…. What we did was let folks opt in into kind of new areas of the product, and now everybody’s opting in.” – Milin Desai Milin says they did not need to do unnatural things to leverage AI as a tailwind. If you are in a situation where a new trend like AI has come out of nowhere to impact what you do or threaten your relevance, it might require a pause and reset. John speaks to the technology adoption lifecycle. There are bleeding edge use cases that apply to only the innovators. Next comes the use cases for innovators and early adopters. John says we can be the late majority to some of the things happening and gives the example of e-mail summaries from AI being an extremely useful of a late majority feature. We can opt into late majority features without opting into everything or opting into the worst possible outcomes of using AI. Milin gives the example of Sentry shipping a grouping feature powered by AI that resulted in big efficiency increases for customers. Most people would not know it’s powered by AI, and it was one of the first capabilities they shipped after implementing some of the internal changes Milin described earlier. Milin says our attention spans are getting shorter and shorter, and some of the capabilities AI can bring are going to help with this. 25:35 – Contextual Communication to Leaders and Parting Thoughts We spoke about the importance of contextual communication from management down to employees at lower levels and even about how important this is when using generative AI tools. Where Nick sees a lot of people struggle is when they are an individual contributor trying to be a contextual communicator upward to leaders. How can we do this well when working with busy leaders in a world where attention spans are getting shorter? Milin says we don’t really think about this. We don’t think about the potential for running into a senior leader at a company and what we would do if they asked us a question. “What tends to happen is you run into somebody who is maybe 1 or 2 levels of ownership higher than you. They ask you a question. You are deep in the weeds of solving a problem, and so you’re so lost in that problem that when you speak to that person…you may miss an opportunity to talk about why you’re solving that problem…. Always remember and always ask early on in your career…why are we doing this? How does this help? Who does it help? Just knowing that and starting to believe in that is helpful.” – Milin Desai Milin says he’s had 1-1s with people who have told him something isn’t going to work. He would prefer them to speak up and question why something is being built if it’s not going to work based on those questions above. “What is the job of somebody two levels up? They are just asking the right questions. What do you think? Is it going to solve the problem?” – Milin Desai Knowing the fundamentals as Milin outlined above (why, how / who something helps) allows you to have a conversation with a leader on the topic, and you can bring a point of view. It helps with what he calls “asynchronous communication” where you end up getting those unexpected questions about how things are going. “Just always ask this – ‘why am I doing this? Who am I doing it for? And then as a result you’ll know the value, you’ll know the persona, and how does it fit in. Those questions then contextualize everything. It doesn’t matter level 1 or level N at that point in time.” – Milin Desai Milin hopes listeners can parse out the value from this conversation. "Just come back to first principles of all the things we talked about. Be insanely curious. Be insanely active. Participate. And then everything kind of flows from there…. At the end of the day, we are only as good as the people around us. And whether you’re a manager listening, you’re an IC…remember, it’s about the humans…. Those people can only help you if you want to be helped. So, you need to take charge and ask and drive the conversation. And there will be a point where you may not be satisfied. We all are impatient. We all want to reach the summit on the very next day. Sometimes it takes time, so you have to understand what level of patience you have. But you own your path, your narrative, your direction…and you need to make sure that you get the most of an organization. I think people tend to forget that. Organizations sometimes get busy. I am not making excuses for people like me and others, but what I am trying to get at is I didn’t get here by waiting for people to give me what I believe was mine…. I actively participated in that conversation. Of course, I then had great mentors who then helped me with it. It did not come right away. I had to wait, be patient. But I’ll tell you, for the most part if you work hard, you’re an active contributor, you’re curious, you have good people you’re working for…things come along. And that formula is going to work. " – Milin Desai We cannot assume an organization is going to do wonders but should be active in the story. Milin is living proof of this. To follow up with Milin on this conversation: Follow him on X – @virtualmilin Follow Milin on LinkedIn Follow what is happening with Sentry: Sentry Blog Mentioned in the Outro There are layers of opting in throughout this discussion: Opting in to use and learn about AI tools is one aspect, and opting in to leverage the tools for the use cases that provide value is another. Milin had to opt in when he moved into the CEO role, and he has created an environment at Sentry that has enabled people within his organization to opt in for leveraging AI to provide more value to customers. Remember those 3 questions Milin mentioned: Why are we doing this? How does it help? Who does it help? Due to life circumstances, our show is moving from a weekly release to releasing every 2 weeks for the time being. We want to make it on a schedule that is sustainable and at the quality we want. When you don’t see a release next Tuesday, it’s because of this change. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

When we use a generative AI tool, providing more context can often lead to better output. What if we could apply this to our communication with other humans? Milin Desai, the CEO of Sentry, says contextualizing communication will change the way you operate. This week in episode 350, we’ll follow Milin’s story of changing companies and pursuing different levels of leadership. Listen closely to learn about the importance and impact of active listening, how practice with written communication can help us develop a clearer narrative, the skills needed in higher levels of leadership, and how we can evaluate new opportunities through the lens of scope and upside. Original Recording Date: 09-29-2025 Milin Desai is currently the CEO of Sentry. If you missed part 1 of our discussion with Milin, check out Episode 349 – Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3). Topics – Customer Discovery and Active Listening, Contextual Communication and Iterating on a Narrative, Scope and Upside, Necessary Skills at Different Leadership Levels, Enabling Active Participation 2:49 – Customer Discovery and Active Listening What Milin said without stating it explicitly was that we need to do a better job of asking people more questions to understand where they are coming from and what they care about. This is what Nick refers to as doing discovery, and it applies to the person working a ticket in IT just as much as the product leader or sales engineer working with a customer. “AI is best when given the best context, so contextualize every conversation. And if you contextualize every conversation, it will change how you operate.” – Milin Desai Milin gives the example of a support technician doing the work to close a ticket for someone but then taking a proactive step to let the submitter know there are other related issues you could help resolve. He classifies this as the “extra step” that some people just do without being asked. Very few people are self-aware and like to rate themselves as the best at different things. “That self-assessment is super important…. That extra juice that people are looking for is that contextualization, that personalization, that dot connecting…that is what will change you. And that comes with being curious, asking the questions, listening…active listening.” – Milin Desai Milin says active listening is difficult for him, but it’s something he has become better at over time. John says sometimes the question a person asks is not the question that person wants the answer to. It’s not up to us to just answer the question that was asked. It’s up to us to go the extra mile and ask questions to get more of the context. Milin shares an anecdote for people in customer-facing roles. Validation that a product pitch is resonating with a customer comes from active listening and questions. But there’s even more. “But you forgot to ask a simple question…in the next six months, if you had a dollar to spend, would you spend it on this? We forget to ask the most important question. If I’m going to build it, will you use it? Will you buy it?” – Milin Desai Without asking the above questions, product teams may relay that feedback from a customer was nothing but positive and not understand why product activation numbers are low. We need to figure out why a customer would use a product or feature rather than assuming they will use it when it is pitched / suggested to them. Be intentional about understanding the customer’s priority as well. “The same principles apply to development and everything else in our lives too. If you only had an hour a day, what would you do with it? Start thinking that way, and it makes things very, very simple.” – Milin Desai Nick says we could also ask about priority when pitching an internal project idea to management. Would someone approve the project in the next six months? John suggests asking how far out in someone’s priority list a project would be. What if your project idea or the product you are pitching is not on someone’s priority list? Should you just stop there? At this point with time left in a meeting you have options. Asking to tell someone what you are building is a mistake, and so is just ending the meeting. “What if you spend the next 5 minutes asking, ‘what is the most important things you’re thinking through?’ Because yes, it may not be the current thing you are doing, but again, coming back to knowing what other people in the company are doing, it could be connected to another initiative, another project, another product that the team is building. So, coming back to the same curiosity we talked about, and knowing what’s happening around you, you may find something. Or you may just learn…. But you came ahead as a high IQ individual who is saving them time, who cares about them more than they care about selling a product.” – Milin Desai It’s important that we learn to pause in this way to gain understanding. Asking someone what they feel is important or what their priorities are after they’ve said something is not a priority is an acknowledgement that what you brought them isn’t relevant. Learning more about the priorities of your audience may bring about an opportunity for a different group / team if you’re plugged into what is happening in other parts of your organization. One option is nothing comes of it, and you learn something. Nick says once we learn what someone thinks is important, we might get a much better idea than what we originally came to the meeting with. 9:00 – Contextual Communication and Iterating on a Narrative John says this goes back to empathizing with the customer and living in their shoes. Part of this job is to collect customer priorities and report it back to your organization. This information might indicate a product a company is building does not solve the right customer problems or doesn’t align with customer priority. From a career perspective, people might think they need to do all of this alone – get on the customer calls, understand what customers want, and synthesize it to relay to other teams. When Milin was a product manager, he started pulling in other team members to be on customer calls with him. This began when Milin was at Riverbed, but Milin tells us he leveraged it much more during his time at VMware. “The interpretation of that conversation can be very different…. After that call is finished, you ask for their interpretation. Did they have happy ears? Did you have happy ears? But more importantly you as a team get on the same page about the opportunity.” – Milin Desai Milin is speaking about promoting collaboration between product managers and engineering teams by ensuring the engineering team members have access to the same set of information. Getting them to hear information straight from a customer helps promote alignment better than receiving feedback only via the product manager who spoke to the customer. Being part of the live conversation is also better than only having access to the recording. Letting other members of your team that you work closely with participate along with you is extremely important according to Milin. You don’t need to do it alone. “So, I think that participation is really important, and the second most important thing in any career progression, anything from non-tech or tech, is communication…contextual communication…. Talking to a VP versus an EVP versus a CRO…everyone is different. We as humans don’t spend enough time on contextual communication in our personal or professional lives. And I would say the single biggest thing I see people make a mistake on is not invest in communication, written form communication….” – Milin Desai If communicating to an engineering team, have them feel they were in that conversation. Give them a synthesis of the problems you talked about and what happened as a result. Storytelling and communication are important to provide your perspective on what happened to others. We can write our thoughts down and then iterate on them. When the thoughts are fully formed, we can share them with a group. Spend time writing down your thoughts, and contextualize them for the audience with which you are sharing them. When we write down our thoughts in draft form, Milin says it should feel natural and not take a lot of time. The story arc can be cleaned up as a next pass / next iteration. John mentions there is a difference between a transient idea and something you take the time to articulate through writing. The latter is something you can understand and have a conversation with others about. John talks about writing as something that enables fully formed thoughts and the evolution of those thoughts. Milin had the opportunity to work for Marin Casado (founder Nicira), and Martin encouraged people to write things down because “you don’t think in PowerPoints.” Milin has developed a habit of writing over time. When he gets an idea, even if it is sitting on a train, he might write it down and save it in his e-mail drafts folder to get it out of his head. Milin will then come back to it later (a day, a week, etc.) to refine it and then share with a larger audience. Martin Casado also encouraged people to think like a story. “The art of storytelling allows you to bring a point of view to the world.” – Milin Desai Nick says this idea of writing, letting it sit for a time, and coming back to refine what you wrote sounds like a great way to prepare for scenario-based interviews. Milin shares some of the feedback he gives people who have completed an internship at Sentry. “Make sure you have a narrative around this. If you choose not to come back to Sentry for a full-time job, when somebody asks you what you did, you have a compelling narrative around what happened and what you learned…. You’re absolutely right. You need to own the narrative and drive it. But you need to find that balance between too much, too little, too boasty, or not telling enough about yourself.” – Milin Desai As we develop a narrative, the brevity and depth might change as we change roles. In Milin’s case, he moved to product management but then began to move into leadership positions. How did he see his narrative change in depth and brevity over time? Milin says it has been the hardest thing. Written form communication is hard. We should be self-aware and self-critical but not let these things affect our confidence. “I just want to make sure everybody understands when I keep saying these things, it’s not about breaking your confidence. It’s knowing who you are and then improving on it.” – Milin Desai Milin tells us he is either very verbose or very succinct, and writing / narrating a full story has taken time to improve. Milin is very good with story arcs, but it’s writing the entire story which is the hard part. “That’s been my strength. I can get you to understand the core, the why, very quickly. But then when I have to make it medium form or long form, I continue to struggle in that. That’s been work in progress.” – Milin Desai This is the contextual communication piece of things. Milin talks about his experience doing all-hands calls as a general manager or as a CEO. Giving too much information in these cases will lose the audience. Most of the time you have to find a middle ground between too much and too little information. Milin says the question-and-answer section of these all-hands calls tells you where the gaps are. He would fill in the gaps either using offline mechanisms or a smaller set of meetings to address these questions. Milin also said it took him a while to get to this point. “And it takes practice to take 3 pages and make it 1 page and make it relevant. It’s really art.” – Milin Desai Maybe AI tools can help here, practice certainly helps, and knowing your audience helps. Knowing your audience is part of contextual communication. Milin says he’s done a lot of iteration and practice to develop these skills. 17:57 – Scope and Upside Regarding Milin’s transition away from Riverbed… Milin says he really enjoyed his time at Riverbed but had hit a wall. In aggregate from a dollars and cents perspective, making the move to VMware was a step down. Six months after making the move, Riverbed stock doubled and split. “But I had zero regret, and this is super important. Why did I move? I moved because I had wanted to spread my wings more, and it looked like the organization that I loved could not make that happen. So, I had to do something about it. I waited, and then I moved on…. I had to take a step down to make that step up. I got lucky…good choice, great people, great mentors at VMware…. I had reached a point where I needed to spread my wings, and that opportunity was not showing up. So, I made the call.” – Milin Desai Everyone has their own reasons for leaving a company. Milin would first encourage us to be patient and not make abrupt decisions. We should seek to leave a company better than when we joined it. When Milin made the decision to leave Riverbed, people immediately thought it was because something was wrong. Nothing was wrong with the company. Milin needed to spread his wings. “Career trajectory does not always have to be a step up. It can be sideways or…down. You look at the opportunity…. I looked at scope, upside, and then I believed that if the scope and upside would work out, things would work out for me. And they did.” – Milin Desai Milin had the opportunity to go and focus on networking at VMware at a time when this was an emerging area of focus within the company. It was a chance to build upon his existing expertise. Milin talks a little bit about his first manager at VMware (Ushan) and how that person’s support accelerated his progression within the company. When the time came, this manager supported Milin taking on a different role within the company. “It’s crazy. I’m telling you…people make people.” – Milin Desai, on having great managers Milin would encourage listeners to optimize for scope and upside, even if you need to take a small detour. In Milin’s case, he did not know many people at VMware when he made the move from Riverbed. It was a risk he took based on the scope of the role he would be in, and it worked out. 21:20 – Necessary Skills at Different Leadership Levels John asks Milin about the difference in skills for each of the roles he has held from individual contributor to first-line manager and upward. John says getting to the next management level does not mean all the skills you had to that point are going to help you (i.e. new skills may be required). “The first thing I am going to tell you is that management is hard. You should know you want it because it’s more than you…. I want everybody kind of walking into that role to realize that it’s a lot of work, and it will never get easy.” – Milin Desai A manager has team members working for them, but there is an additional burden that requires translation of the greater organization’s expectations to your team. Milin says the skills you need as a manager are not something you can take a class to gain but rather something you learn over time. We can also learn from the great managers we’ve had. Milin knew what great managers looked like. They let him be himself, allowed him to take initiative, had high expectations, and they gave him context. Milin found it easy to manage people who were like him, but his biggest lesson was adjusting to the different ways in which people on the team operate and bring value. It was important to create a forum to enable all types of people to succeed. John says we learn how we as individuals are managed well (because it is modeled for us) but not necessarily how to best manage people who need to be managed differently (i.e. needing different types of guidance / structure / guardrails, etc.). Milin continues to struggle with this. Milin likes to be pointed in a direction by a manager, and he can do the rest. Milin would come to a manager with problems when needed, but he will figure out how to get what he wants from a manager. Milin reminds us of the time he was asked to go find a new role and how much it changed him. Learning how to manage people different than you is a skill that takes time to acquire. “There’s a point in time when it’s not about you or what you bring to a team. It’s about who you can hire….” – Milin Desai, on an aspect of rising to more senior leadership levels When Milin was moving up to senior vice president, it became more about whether he could bring in exceptional senior talent. This kind of caught him by surprise, but Milin knew he could go and figure out how to do it well even though it might not have come naturally to him. This was a new aspect of leadership after he had gained experience running a business unit and making it profitable. “If you bring in the right people, you automatically become potentially a great manager because they unburden you. They understand you really well.” – Milin Desai Milin says we should be willing to bring in people who are smarter than us, and we should be ok with that. He’s never had an issue with it, but some people do. Hiring the right people is a form of leaving an organization in a better state than you found it. Moving on from people is also something you learn as you move up. Milin calls this active management. “There’s a point in time where a person could be doing everything they are supposed to be doing. They have been with the organization, but the organization has shifted…. And this person is not able to adapt to it. It’s the company transitioning at that point. It’s not the person. And the ability for you to quickly recognize that for this phase of the journey…somebody you had loved before is not going to work out is probably one of the hardest things you will do as a people leader.” – Milin Desai When John was at Google, they talked about rearchitecting a product when the user base increases by a factor of ten. Similarly, the people organization has to be rearchitected. “There is a journey of an organization. It is a living, breathing thing, and it goes through its own phases. And through that phase, there are some people who grow through every phase and continue to be part of the organization…. There is a time when somebody who was a perfect fit no longer is a fit…. To identify that and to make that person successful in a different role in the company or something else…those were the things I had to…learn at these different levels. It’s hard.” – Milin Desai Some employees may only be part of 1 or a couple of phases of an organization’s growth / change. Milin gives the example of people later in their careers who are very self-aware. They might understand that the most enjoyment for them is found when they work in startups that have between $10 million and $100 million in annual recurring revenue, for example. Milin shares the example of bringing in someone to work with him who helped build a specific team and then others who helped scale the team and greater organization. Other senior leaders taught Milin that bringing in the right kind of senior talent would free up some of his bandwidth to be spent in other areas. Milin says he has luckily not needed to let people go because a business was not profitable. “Through that journey, the thing that has inherently worked, continues to work, is writing down my intention for the org, for the team, for the company…what we will bring to the table and keeping that written and clean 24 by 7. It doesn’t become stale…. That has been the consistent point of help besides having great people to work for.” – Milin Desai According to Milin, someone can write an 18-month strategy, but they should go and clean it up every 3 months. 29:55 – Enabling Active Participation Nick says by maintaining clarity on all of these things, it cascades to help leaders like Milin understand what the roles and job requirements within the organization should be, even if they are not formally changed. Milin says having it written down helps with everything. “It’s super hard to cascade a point of view or a vision. You have to repeat it multiple times, in multiple forums, and everything else. But if that itself is stale…it becomes really hard. So, I still to this day tell everyone, ‘give me a one-pager of where you’re taking the team for the next 3-6 months. If you don’t have that, how will you be effective?’” – Milin Desai The one-pager Milin mentioned is different than a feature or function to be built. It’s more about outlining the set of problems a team will solve in the short term (i.e. next 6 months) and then coming up with the measurements of how to do it within that specific time frame. He suggests highlighting the longer-term problems the team wants to solve as well. These things are written down and get revisited regularly by the team (maybe every 3 months) to determine if they are still relevant. Milin calls this “active participation.” “Are these still relevant? I want you all to think about it. Active participation, right? Now they get a point of view on the 3 things next six months we agree and the 4 things long term maybe we need to change or something like that. So that allows for active participation. I would say that’s another great thing I learned as my roles started getting bigger and the scope started getting bigger.” – Milin Desai Mentioned in the Outro Contextual communication has many layers to it. We can share context verbally with others but also gain it from them in the way we ask questions. We can also provide context to others through writing. Milin has done this for a long time. He will write a draft and iterate on it regularly to keep it fresh and clear. Duncan Epping uses writing to learn Episode 303 – Write to Learn and Learn to Present with Duncan Epping (1/2) Jason Belk emphasized developing his narrative through writing before talking about it Episode 284 – Draft Your Narrative: Writing and Building a Technical Portfolio with Jason Belk (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

How curious do you think you are at work? Take a second to rate yourself. After today’s conversation with guest Milin Desai, you’re going to want to dial that curiosity up a notch. Milin is currently the CEO of Sentry, and one of the keys to his success from the very beginning was allowing the scope of his curiosity to expand over time…beyond specific projects and even beyond his job role. Perhaps without realizing it, Milin was doing the work to build and maintain professional relevance. Listen closely in episode 349 as we follow Milin from his early days as a computer science student through roles as a QA tester and software developer all the way into technical marketing. You’ll hear advice for expanding your own curiosity inside your current company, ways you can provide value to a mentor, and an empathetic approach to customer conversations that can help you build relevance and develop a strong reputation. Original Recording Date: 09-29-2025 Topics – Meet Milin Desai, A Unique Trait, Internships and Job Interviews, Curiosity and the Importance of Control, Mentorship as a Stream of Active Conversations, Beyond the Scope, Becoming Relevant in Something Different 2:40 – Meet Milin Desai Milin Desai is currently the CEO of Sentry. Sentry helps teams find where code is broken in production and helps them fix it fast, and with AI, fixing it faster is greatly accelerated. 3:15 – A Unique Trait Around 7th or 8th grade Milin recognized how much he enjoyed math and science in school. Milin had an affinity for STEM (Science, Technology, Engineering, and Mathematics). Milin cites his dad, a mechanical and electrical engineer, as a big influence. Going into 10th grade, Milin thought he would pursue mechanical engineering. Milin’s cousin Rajiv (who had worked for NASA) would come visit and began showing Milin some of the work he was doing. This is the point at which “everything changed” for Milin, and he decided to pursue computer engineering / computer science. Milin also tells us he built hundreds of websites in India during the time of dial up modems. Milin pursued an undergraduate degree at a school in Mumbai, but his family knew he wanted to come to the United States. Milin came to the United States in 1999 and attended USC (University of Southern California) to purse a master’s degree. The potential for opportunity and the vastness of the United States captivated Milin. Did Milin ever ask Rajiv what he should study, or did he naturally gravitate toward those areas? Rajiv would have conversations with Milina and show him the work he was doing. Milin started working for Rajiv while pursuing his undergraduate degree. He was building websites for companies in India. The building of the websites was interesting to Milin, but he was also doing the selling part. Milin had to make a pitch to companies explaining what a website could do for them, share the price, and collect the check if they said yes. “Not only did he influence me in kind of figuring out…this is where the opportunity is and inspire me…but he also went on to tell me that I have a unique trait where I can talk business tech selling, and I know the technology part. And I can bridge the two worlds. He was one of the early people to recommend that in the long run I may want to think about the business side or…the entrepreneurship side of things when it comes to tech, not just the programming or the systems side of things. And he in fact felt my combo made me more relevant…in that lane versus just staying a programmer.” – Milin Desai Rajiv gave Milin these cues early on in addition to inspiring him to do the work. As people who work in sales engineering today, John and Nick agree that the combination of technology and business value is very valuable. 7:49 – Internships and Job Interviews Milin began working for Veritas after he finished his master’s program as an entry-level software engineer. Pursuing an advanced degree can give you the chance to pursue internships, and Milin had a family friend working at Veritas who introduced him to the hiring manager for a quality assurance (or QA) internship. After successfully getting the internship at Veritas, Milin was doing QA for software-defined storage volume management. Milin’s work during the internship led to a full-time offer from Veritas upon his graduation. “The first break is always hard, by the way, to get. I see it even to this day with folks coming out of school. Not everyone…lands in the perfect opportunity right away, and the dots need to be connected. I’ve been fortunate enough to have people open doors and open opportunities…. But I remember being rejected a lot.” – Milin Desai Milin tells us he struggled in job interviews as a new graduate. Many of his friends from school had multiple job offers from these conversations, and compared to them, Milin had much less success getting offers outside of the one from Veritas. From a timing perspective, this was around the time of the market crash following the events of September 11, 2001. “Even timing-wise, the difference between graduating with your master’s degree a year and a half versus 2 years. That six months made all the difference. A little luck, a little timing, and a lot of support.” – Milin Desai Did the degree program Milin pursued prepare students for job interviews at all? Milin tells us that a school doesn’t really prepare you for the conversation you have in an interview. While you do learn deep systems concepts in school, for example, the interview questions are often situational. “You definitely use those concepts, but you’re never in that setup until you go through that process. And I think interviewing is a little bit of an art form. Some folks are really good at it, and some folks even study it. There is some element of that. But I think the school prepares you with fundamentals. It doesn’t necessarily prepare you for that interview per se, and you have to kind of connect the dots…. You can prepare for it. Some people are just naturally good at it, and some people like me just suck at it.” – Milin Desai Milin feels interviewing is sort of an art form. You can work to prepare yourself Did Milin think of interviews as somewhat similar to pitching a company on a website? The selling part is easy according to Milin. In this motion you are telling a story, bringing a problem statement, and delivering value. It’s less about solving some kind of algorithm but rather trying to figure out if what you have to offer will address someone’s pain point. Milin emphasizes the storytelling element of the sales process and the collaborative problem solving you’re doing with someone. It’s more of a conversation. Selling is not about getting into an extreme level of detail like a technical interview can be. Someone could easily make a mistake in a technical interview when describing a specific step in the process and get off track. People can feel a great deal of pressure when in a job interview. Milin feels job interviews are much more difficult than a business conversation. The latter is about human connection and building rapport with the other person. Milin tells us his interview style is more about building human connections than testing the limits of a person’s technical depth. John mentions the difficulty in choosing a technical interview style that is well suited for effectively evaluating multiple job candidates. Does having a portfolio of code that is applicable to the role help with this? John also brings up LeetCode style interviews if you’d like to read more about them. Milin says quickly assessing a fit can be a challenge. It can be a combination of skills and experiences with other things layered on top. Milin says the first interview might be more focused on solving some basic elements. But it’s helpful if a candidate can talk about and contextualize other work they have done (like working on an open-source project, for example). "But to get in, there has to be a common baseline, a language, a form…. " – Milin Desai, on early round interviews If interviews are challenging for you as they have been for Milin, you have to work through them over time. “In the later stages what I would tell you is what is most attractive is people who have been from what I call 0 to 1 project where they start something are through the end. The end is not shipping actually. Shipping is just an intermediate point. End is adoption and the scaling and all of those elements. And to be through that journey 1, 2, 3 times is interesting to almost every organization out there…because through that you learn a sense of people, ownership, outcomes.” – Milin Desai Early on the baseline is some kind of entry test. When looking for people with more experience, interviewers will ask about projects people have written about on their resume or elsewhere and how they solved problems within those projects. At this point, the portfolio becomes more interesting and can help you get an opportunity. We emphasize the importance of a portfolio of projects and not just a portfolio of code. 16:16 – Curiosity and the Importance of Control How did the role Milin had at Veritas shape the rest of his career? Milin says this was his first job and was an amazing experience that has filled him with fond memories of that time. Milin emphasizes the importance of help from others during the course of his career. The Veritas experience gave Milin the chance to work with great people, but he also found mentors within his area at the time (software volume management). Milin mentions a mentor named Mark who remains a dear friend to this day. “He kind of took me under his wing and explained stuff and was just there. And he didn’t need to do that…. Please, when somebody…experienced takes the time to go that extra mile you make sure you better jump on and do what’s needed. That was a friendship and mentorship I would say on a regular basis that really helped shaped my system thinking…. It was just the way we would talk about systems and concepts, and it really kind of expanded my mind…. The discussions are not always about this piece of code as much as how does this work with this part of the system…?” – Milin Desai Mark was in a leadership role at the company and understood other projects that were in the works. Milin really enjoyed learning about those things even though they were outside his area. Milin emphasizes the importance of curiosity that extends beyond what we own and even what others own. This ever-expanding curiosity was one of the most helpful things in addition to mentors early in Milin’s career. We should also be willing to raise our hands to volunteer to solve a problem or work on something extra. This quality, in conjunction with being curious and having effective mentors, was essential to Milin’s success. After completing his first year at Veritas and getting a great review, Milin’s manager told him he needed to find a different role. This was not about job performance. “I’ll tell you the positive out of it. It basically made me realize that I need to control my destiny. I need to keep working at it, not assume anything. It was the best thing that happened to me…. At that point in time, I found a different role. I found another set of great mentors. And things just took off because my mindset shifted from not just being curious and raising my hand. It changed into…I’ve got to take care of myself. No one else will. It was a healthy sense of paranoia of constantly wanting to prove myself. Again, not lack of confidence, impostor syndrome…none of that stuff. It was just about ‘am I doing everything absolutely possible that I become unshakeable?’ That was the most helpful thing that person did for me, but it changed everything.” – Milin Desai Did the manager who mentioned Milin would need to find a different role tell him he needed to search inside the company or externally? Milin had to go do the homework to assess his options for new roles. It was up to him to make it happen. “Being curious means you work beyond your project scope, you talk to other people, you get to know other teams. They get to know you. So, when something like this happens it is not like you just showed up at their door. It’s all connected in a way when you are part of something bigger than your project, your team. You take interest. You have conversations. You have lunch with people beyond your team. You do things kind of outside just general scope.” – Milin Desai, on curiosity as a network builder When a job loss type of situation happens and people know you, it is a jumpstart on internal opportunities. A mentor, for example, might vouch for you as well when trying for a new role. “At the end of the day there are humans involved in the process, and that’s where the first connection happens.” – Milin Desai 22:43 – Mentorship as a Stream of Active Conversations As Milin looks back, how would he describe ways we can be an effective mentee to a mentor? It’s not about showing up unprepared and expecting magical wisdom to come from a mentor. It’s also not about taking a wide set of problems. “It’s an active conversation. It’s a relationship. And the relationship is not transactional…. It’s a constant stream of active conversations….” – Milin Desai We should go into a meeting with our mentor prepared just like a board meeting. Take with you a set of 1-3 things the mentor could help you with. Milin suggests we figure out how the mentor operates, and figure out how to leverage this. It’s about reverse engineering what a mentor brings to see if they can bring value to you. “And it’s not like they are going to help you suddenly go from point A to point B. I think that’s another big misnomer around this. It’s just somebody as a guide point, as a reference point of…additional data.” – Milin Desai When Milin looks back at the people who have helped him, most mentors were within the same company, but there were external mentors as well. People tend to think a mentor only helps them (a unidirectional relationship). Throughout Milin’s career, he tried to find ways to help his mentors (i.e. taking something off the mentor’s plate). “It became a mutually beneficial thing where they were being successful as well in spending time with someone like me…. It’s various phases, but I always tell people there is no professional mentor. There are professional coaches. That’s different.” – Milin Desai Milin says active mentorship on scenarios or career things requires someone be in the business with you (in the same company), and it also benefits the mentor. People confuse mentors and coaches, but any given person may need both an external coach and internal support systems (like symbiotic relationships with mentors). Was it the series of active conversations with mentors that pushed Milin in the direction of product management? Milin encourages us to think back to his time focusing on storytelling and selling before graduating and put it together with his curiosity during his first year at Veritas. Milin mentions spending time with leaders who worked across different functions of the company and how interesting it was to learn about interconnected projects across the company. Now we fast forward to the time after Milin needed to find a new role. “By the way, I was an average coder, but I made up for it with a lot of testing – making sure that it worked, it worked in different scenarios, the UX, the experience…. That’s where I learned…everything is about the user, not about me writing code.” – Milin Desai Milin would send e-mails to product leaders inside the company asking if they had explored specific problem domains. He would make these messages thoughtful and include research. He would also ask questions offline after all-hands calls. Milin mentions names like Jeremy Burton and Mike Spicer as leaders who took the time to respond to his messages. The continued dialogue with product leaders helped Milin realize he wanted to try something different. “I wanted to kind of go to the product definition side because I was really enjoying it, but it was a series of all of these coming together to that culmination. That encouragement, that active encouragement from the folks I just mentioned definitely also helped….” – Milin Desai 29:52 – Beyond the Scope Did Milin have any conversations with his manager at the time about pursuing product management before he made the move? Milin feels he may have been operating like a product manager in some form by asking the right questions and being a little disruptive. He thinks people started to see this. Milin’s next role was a technical marketing engineer at Riverbed. He did have the option to become a product manager under Symantec but chose to go to Riverbed. “I made the shift first to a technical marketing engineer, and within a year they said…move over to product management…. I think people realized my aptitude, the way I was spending time, the contributions I was bringing…. I think I had to just make up my mind and start making that choice, which is what I did in 2006.” – Milin Desai John emphasizes that we do not always know how the puzzle pieces of experience will fit together later. Without exposure to different things, there is no way to put these together when it’s needed. Milin says many people want to join startups because it will allow them to do many different things in an organization with fewer people. While this is true, not everyone takes advantage of everything a startup can offer in this regard. While it is likely harder in a large organization to do this (do many different things to gain different experience), it is not impossible according to Milin. In fact, he’s changed roles within large organizations to do different things over the course of his career. “There is so much you can learn by just inherently listening for the signals, being curious about it, having lunch with different folks.” – Milin Desai Milin tells us that having lunch with different people or participating in extracurricular activities with your team can be a great time for networking. It’s something that takes you outside the scope of your role, and when you do it, you do not know where it might take you. Milin used to play soccer during lunch, for example, which gave him the chance to network with people in the bay area. Milin says we do not need to be extroverts and should do what is most comfortable for us. "If you’re a curious person and you want to learn a little bit about marketing, you can just ask. And most organizations have good people. They will respond, which is what I was telling you about when I was talking to…all these people who were like 7 levels above me in the larger organization…. They chose to take the time to respond, which created encouragement…. " – Milin Desai John says these are practical tips in going from 0 to 1 in one’s own career management. 33:40 – Becoming Relevant in Something Different What led Milin to apply for the technical marketing engineer role? It started by being ready to do something different. “I don’t even remember how I applied for it, but all I can tell you is when I spoke to the team and the people I was like, ‘wow. This is going to be so much fun.’” – Milin Desai The role as a technical marketing engineer was really about telling people how to use a Riverbed product focused on WAN optimization. We might call it developer experience or developer advocacy today. In the job interview, there were no questions about coding because this was a technical marketing job. But they gave Milin a homework assignment as part of the interview to share how he would test something. According to the hiring manager at the time, (Phil), Milin went above and beyond for this assignment. In addition to explaining how he would do the testing, Milin built a PowerPoint representing the story he would use to educate people on this scenario complete with preconditions, advantages, etc. It was the extra push on this exercise that got Milin the job. At the time, Milin didn’t understand what it meant to work for a pre-IPO company (which Riverbed was at the time). “But I didn’t even think about all this stuff. I just literally loved the people and the scope of the role, and I felt like this would be exciting. And I took it…. There will be a point in time in your career where you can choose the people you work for and choose the people you work with, and there is nothing more important than those two things in my opinion when thinking of what you want to do next. Where do you want to spend your time? And most people don’t optimize for that. They optimize for everything else…. Day to day, you’re going to spend more time with these people. As soon as I got to know this group I am like, ‘man, I want to be with this group.’ …It was the people. Just like everywhere else…it starts with people.” – Milin Desai John mentions part of technical marketing roles as well as developer relations roles is being what he likes to call “nerd famous.” You have to be a little bit of a draw for attendees. Does this align with Milin’s experience in technical marketing? Milin says yes and no. He feels the people who succeed in these roles are there because they have depth. “That, I think, should not be lost. There have been a lot of people who have come and gone if you notice in that…what people call devrel or whatever…. The ones who have survived and thrived and continue to be respected are the ones with depth.” – Milin Desai Whether it’s writing a product design document or an engineering design document, Milin tells us it is a story very much like a movie script with a beginning, middle, and end. Great storytellers who can simplify things will do well in a technical marketing or similar role. Another thing to consider is whether you are bringing value. If someone comes to talk to you about cooking and you love eating but not cooking, the conversation is kind of pointless. “When you are not famous, the way you become relevant is you bring relevance to the other person in terms of what they care about and then to be able to help solve their problem.” – Milin Desai Milin says when it comes to people in customer facing roles (product managers and many others), it is easy to get into “the diarrhea of our mindset.” People get into the mindset that they are building a feature and need to tell the customer everything about it. And sometimes customers will just let you tell them. “If you pause a little bit, understand what the other side wants, do the storytelling from that standpoint…highly, highly transformational.” – Milin Desai Milin also tells us that keeping our word helps build our professional brand. Are we doing what we say we will do? Getting someone an answer because you said you would, even if the answer is no, build rapport and relationship. The personality aspect is needed to get the best opportunities according to Milin. Milin gives the example of posting some information on bulletin boards about using Riverbed and NetApp together. People got to know him through the content he had shared and the value it brought them. Listen to the specifics of what happened when people would meet him in person. “I feel like if you do it right, you do it for your audience, you know your audience…day in the life of…be in their shoes. I think that’s super important in that TME role, in the product manager role versus the internal, inside view of…we are building something. Nobody cares about your algorithm if it doesn’t work. So, tell me how I am going to use it. If it breaks, tell me when it’s broken…all of that fun stuff. Live in the life, live in the shoes of your customer. Understand what they want, empathize with that, and from there, magic will happen.” – Milin Desai Mentioned in the Outro There is a slow build of through Milin’s experience of developing that relevance. Examples would be: Discussions with early mentors to understand systems and how projects within the company were connected It takes curiosity to understand these things, and we need to have that same kind of curiosity when we help our co-workers or external customers with technical problems. The questions Milin would ask and suggestions he would make to senior product leaders Taking the time to put together thoughtful questions and suggestions made Milin relevant to those leaders, and they took the time to respond to his messages. That kind of thing does not happen unless you are bringing something relevant. Creating the content at Riverbed Milin was relevant to others because of the content he created. We can build relevance through content we create as part of our portfolio of work / public proof of work. Much of Milin’s relevance came after he listened well or listened actively to be thoughtful in his responses. This is what we should be doing in any role that has customers (externally facing or internal customers). If you’re in IT, your customers are the people whose problems you are trying to solve or those for whom you are trying to provide a technical solution. Optimizing who we work for and who we work with is another way to remain relevant. If we like who we work for and with we will want to provide value to them and therefore remain relevant as a member of that team. We talked about mentorship in Milin’s career and the bidirectional value flow between mentor and mentee, emphasizing that the mentee should try to bring value to a mentor. For more discussions about mentoring, check out episodes under the mentoring tag on our website. We would also point you to 2 specific episodes that represent a masterclass in mentoring: Episode 288 – Guardrails for Growth: A Mentor’s Experience with Dale McKay (1/2) Episode 289 – Enhance Your Personal Brand: Feedback as a Catalyst for Change with Dale McKay (2/2) Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.

As managers inherit larger teams inside flatter organizations, we might immediately point out the challenges. But what about opportunities? Despite the trend, those who seek to lead (in a management capacity or otherwise) have the chance to intentionally build a better culture. We pulled in former guests Shailvi Wakhlu, Neil Thompson, and Abby Clobridge in a roundtable format to get actionable strategies. In episode 348, we present actionable strategies for managers and individual contributors to thrive in this new environment. Listen closely to understand the importance of improving one’s communication skills, the unique opportunity and impact of the player coach / team lead, the critical elements of a manager’s role, and advice for job seekers in a tough market. Original Recording Date: 09-27-2025 Topics – Framing Part 2 of Our Discussion, Opportunity for the Player Coach, Modeling the Benefits of Improved Communication Skills, Management Support of Strong Communicators, Individual Contributors and Communication, Succeeding as a Manager of a Large Team, The Culture of Large Teams, Advice for Job Seekers in a Tough Market, In Closing 1:01 – Framing Part 2 of Our Discussion Last week in Episode 347 – Organizational Flattening: Understanding the Trend, Career Challenges, and Opportunities (1/2), we introduced a slightly different format that we’re continuing this week based on an industry trend. The trend of organizational flattening in our industry has been top of mind for us. We’re seeing the continued layoffs in tech often times result in fewer management layers and an increase in the number of people reporting to a single manager. This topic is too big and has too many angles for a single conversation. We wanted to bring together multiple expert perspectives on this issue in a single episode. We’ve reached out to a handful of former guests and sent them specific questions on this topic. Those guests were kind enough to record their answers and send them back to us. Consider this a Nerd Journey roundtable or collection of hot takes from trusted voices. Our goal is to amplify their advice and provide a diverse set of strategies for navigating this landscape. In the first episode (last week), we explored the trend of flatter organizations and the consequences for your career path and team culture. This week in part 2 we will focus on actionable insights for thriving in this environment. Here’s the full set of episode links we will share throughout the conversation if you would like to hear more from one of the former guests who participated: Shailvi Wakhlu Episode 210 – A Collection of Ambiguous Experiments with Shailvi Wakhlu (1/2) Episode 211 – Structure the Levels of Contribution with Shailvi Wakhlu (2/2) Self-Advocacy: Your Guide to Getting What You Deserve at Work by Shailvi Wakhlu A special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course can be found here. Neil Thompson Episode 193 – Communication for Specialists with Neil Thompson (1/2) Episode 194 – Question Askers and Problem Solvers with Neil Thompson (2/2) Teach the Geek YouTube Channel Abby Clobridge Episode 292 – Library Science: Information Architecture and the Synthesis of Details with Abby Clobridge (1/2) Episode 293 – Enterprise Knowledge Management: A Consultative Approach to Solving the Right Problems with Abby Clobridge (2/2) 1:42 – Opportunity for the Player Coach We’ll start by discussing the opportunity of being a player coach (another way we often reference the team lead or tech lead role). Shailvi Wakhlu is a leadership speaker and data consultant with experience building and leading large organizations, including structuring of job levels for career paths. We spoke to her in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work. Our question for Shailvi: As organizations flatten and there are less manager roles, does this create an opportunity for people to become a technical lead or team lead to help the manager scale? We would love to hear any perspective you have on how the team lead / tech lead (i.e. player coach type role) changes as a result of the org changes. Even without the trend of flattening or decreasing the number of managers, there has consistently been an opportunity for people to demonstrate the mindset of group leadership. Someone could be a project lead, a team lead, or a technical lead. The technical lead focuses more on technical standards to which a team needs to adhere. “I think anything that you do that helps your manager manage the team, scale the team, grow the output, or just have better focus…has always been a good way to get your foot in the door for those type of roles in the future.” – Shailvi Wakhlu Shailvi remembers working at companies where several people wanted to someday get into a management role. Even in times of heavy hiring, there is no way to accommodate everyone who wants to eventually do this. People stepping into those lead roles would have a leg up on other candidates for future management roles. “If I see somebody is doing a fantastic job of managing a project, I know that there is a subset of manager responsibilities that they’re able to handle. If I see them doing team events…if I see them stepping up on technical leadership, defining standards…all of these things kind of point to that same larger skillset. And I always encourage that even if there is no formal capacity in which you can do this, even if you create your own opportunity and showcase that…this is a space where I see our team could improve…even without the manager title I think you have plenty of options to contribute at that stage…and definitely in this type of a market where there are less manager roles.” – Shailvi Wakhlu Shailvi believes the job market will bounce back, and when it does, there will not be enough people who have been managers and have done things like performance management, skill assessment, and hiring. People who can showcase they have some of this experience and the right mindset have a good start toward landing a management role. Before Shailvi was a manager, she was the hiring lead on her team of 2 people. Shailvi defined the standards (measurements, rubrics, etc.) for the interview process. She tells us doing this made it far easier to transition into a full-time manager role. 5:25 – Modeling the Benefits of Improved Communication Skills We wanted a perspective on communication in this current climate and reached out to a former guest with expertise in this area. Neil Thompson is the founder of Teach the Geek, an organization that helps technical professionals in STEM (science, technology, engineering, and mathematics) improve their public speaking and presentation skills. He’s also the host of the Teach the Geek Podcast. We originally spoke to Neil in episodes 193 and 194. Here’s what we asked Neil: How do you think team leads or technical leads (sort of that player coach role) play into the development of strong communicators? Where do they help people where managers cannot? Players (or individual contributors on a team) don’t see themselves as managers and would not be modeling themselves after managers. A player coach is way closer to each member of the team’s current role than a manager. Player coaches who are adept at communicating well can model these skills for other members of technical staff and educate them on the benefits (and potential opportunities) of improving their communication skills. Neil points out it could very well be a player coach was moved into that role because of their communication skills. Technical staff members are far more likely to want to invest in improving their communication skills once they see and understand the benefits of doing so (thanks to the modeling of player coaches). 7:09 – Management Support of Strong Communicators Another question we had for Neil: "What challenges will managers face trying to develop good communicators when their team is huge, and what can they do to be more effective when this happens? With a large team, one challenge will be getting buy-in from all team members on the idea of improving their speaking skills. Assuming this is the case within your organization…Neil encourages leaders to let their direct reports know that improving speaking skills increases visibility within the organization, and opportunities tend to come to those with greater visibility. Technical people will not want to be passed over for opportunities based on something they can control, especially if they recognize the reasons others have been given new opportunities was due to improved communication skills. And they would certainly be motivated to improve communication with decision makers who can give them opportunity. As part of his work at Teach the Geek, Neil encourages companies to develop speaker training programs for developing technical staff members. One challenge to this approach is getting technical staff to agree on the priorities of this kind of training program. Neil suggests sending out a survey to technical staff members to make sure this is well understood. Technical staff may want to understand how to better engage an audience, get ideas for balancing technical depth and clarity, ways to minimize the use of jargon, etc. If you do take a survey of technical staff, incorporate at least the top 3 priorities as indicated by survey results into a speaker training program. 9:07 – Individual Contributors and Communication We also wanted to know from Neil: How can the individual contributor develop those strong communication skills to build rapport and communicate the value of their work to a busy leader? If technical staff members have gone through a speaker training program like was mentioned earlier, they will want to look for opportunities to practice continued development of those skills. Neil highlights the importance of organizations offering speaking practice opportunities for members of technical staff. One easy way to do this is through a lunch and learn. This forum is a great way to allow people to give presentations covering their work progress / accomplishments that both managers and even non-technical staff members can listen to and learn from. Neil points out the usefulness of this information for nontechnical staff members such as HR personnel responsible for screening job candidates. Sitting in on these presentations can, for example, improve the quality of those screening conversations and overall candidate selection rather than relying solely on job descriptions which may be outdated. 10:31 – Succeeding as a Manager of a Large Team Another question for Shailvi: What are your top suggestions for succeeding as a manager of a large team in this environment? Shailvi says in today’s environment, the definition of a larger team of direct reports has changed. “A few years back that large team definition was…more than 8. Nowadays I think it’s very common to see people who have 8, 10, 12, 15 direct reports…and nobody’s blinking an eye.” – Shailvi Wakhlu At her previous job, Shailvi had 6 direct results that trickled down to an organization of 30 people total reporting up to her. Success when you have a large number of direct reports takes a lot of intentionality. “What is your role as a manager? One is to provide clarity for your team to make sure they are aligned with business goals…to make sure they know what is going to be rewarded, what is not rewarded, things like that. The other big piece is making sure you are available to help grow the careers of everybody who has taken a chance on you and is putting the fate of their careers…in your hands. So how do you make sure you do those two pieces successfully?” – Shailvi Wakhlu Shailvi emphasizes the importance of streamlining communication and information sharing in both directions (from you to your employees and in the other direction). Make sure people know what they can expect from you. Do people know what you will communicate and when you will communicate it? For example, will you openly communicate the necessary context so that people can effectively recalibrate? Do people have the psychological safety to share their challenges and concerns with you? Are team members comfortable sharing their professional goals with you (i.e. opportunities and growth areas), and are you providing critical feedback to support pursuit of these goals? Shailvi also highlights the way a manager delegates as key to success. Having a large team means there is opportunity for people who want to move into some type of leadership role to gain experience. “It’s very important to make sure that you are public in your appreciation for people who help you in the smooth running of the team…. If it’s a non-promotable task…if it’s a housekeeping task that nobody’s ever going to get promoted because of…do not outsource that. I think you do a disservice to people’s careers if you’re asking them to do…general housekeeping and you’re basically asking them to do it above their existing job. And, you’re never going to consider that work important enough to actually think that they’re performing at a higher level. So, delegate work that is actually useful. Delegate work that is actually helping them improve their skills and their visibility in showcasing that they have leadership capabilities….” – Shailvi Wakhlu, on managers delegating responsibility which allows the right type of experience 14:48 – The Culture of Large Teams One last question for Shailvi: How can leaders create a culture that is impactful within their organization when the structure of the organization is designed to allow less time spent with each person underneath a leader? Shailvi feels this is extremely relevant in a world where managers have too many people reporting to them. There is often not enough time to get information flowing between the manager and direct reports for the benefit of the company. Some of the work Shailvi does as a consultant is with organizations who want to build strong teams optimized for performance, productivity, and profitability. “I feel that…leaders tend to anchor on the limited time they have with all the people who report up to them that they just sort of spend that in getting status updates…. It’s very one-sided.” – Shailvi Wakhlu Status updates can be shared in an e-mail or updated on a JIRA board. “The part that I encourage leaders to think about is how do you create a situation where everybody on your team understands the link between their work and business success…where there is no ambiguity about it, where they clearly understand…this is the part of my job that is going to help the company succeed? And that is how you build that excitement with people….” – Shailvi Wakhlu A sense of personal ownership usually breeds accountability. To them it won’t just be finishing a project but rather helping the company succeed with a specific goal. “Creating that culture of transparency, open communication…I think that is something that takes intentionality on the part of the managers. It takes repetition where you keep showcasing how you’re rewarding work, how you are setting expectations. You can’t have unevenness….” – Shailvi Wakhlu Leaders should use the limited time they have with employees to understand their motivations. Work to help your people with their careers, help them understand the opportunity in front of them, and consistently provide clarity. “How you show up as a leader is something that is more important than anything else that you say. Are you accountable for your own actions? Are you taking ownership of larger pieces that are under your area of ownership? When leaders can…structure what they want to spend time on, it goes a really long way.” – Shailvi Wakhlu 17:57 – Advice for Job Seekers in a Tough Market To close our discussion, we wanted some actionable advice for navigating a tough job market. We’ll hear once again from Abby Clobridge. Abby is the founder and principal consultant at FireOak Strategies and has deep expertise in the realm of knowledge management. Abby was a guest in episodes 292 and 293. Our question for Abby: In a tough job market, what do you think job seekers should be doing to stand out that maybe they aren’t right now? Treat your job search like you would a portfolio project. Show what you are doing and what you are learning by building something tangible. It could be automating something, creating a dashboard, or writing a blog describing how you would solve a problem. Abby says we can also host micro conversations made up of 3-4 peers, mentors, or formal colleagues in a roundtable format. These can be virtual or in-person. This can strengthen your network and benefit everyone involved. We can also practice visible curiosity by posting about a book we read or a tool we used. Abby calls this “learning out loud” and something that can act as a signal to future employers that we are engaged, adaptable, and someone who wants to connect people. 19:12 – In Closing We want to say a huge thank you to all of the guests who contributed to this episode! If you want to hear more from them, you can find the full conversations… Abby Clobridge was a guest in episodes 292 and 293. We spoke to Shailvi Wakhlu in episodes 210 and 211 She’s also the author of Self-Advocacy: Your Guide to Getting What You Deserve at Work. Here’s a special 15% off link for Nerd Journey listeners to Shailvi’s self-advocacy course. We spoke to Neil Thompson in episodes 193 and 194. What did you think of this format, and what other questions need to be answered on this topic? Send us an e-mail at [email protected] to chime in. Contact the Hosts The hosts of Nerd Journey are John White and Nick Korte. E-mail: [email protected] DM us on Twitter/X @NerdJourney Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_ Leave a Comment on Your Favorite Episode on YouTube If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page. If uncertainty is getting to you, check out or Career Uncertainty Action Guide with a checklist of actions to take control during uncertain periods and AI prompts to help you think through topics like navigating a recent layoff, financial planning, or managing your mindset and being overwhelmed.