Staying in business can be difficult at times. Critical skills that are required to build a business exist and grow year after year. All business owners, at one time or another, find themselves struggling to keep clients (retention), to keep up with what customers want from the company (experience), and to add people (increase products).

Over the last 20 years, Jess Dewell has worked on many of these problems with companies and clients. When there is a chasm to cross, she points it out and cultivates the team to figure out how to build a way across.

Professional and thoughtful, she brings to the table.

Transcript of the Interview

Hugh Ballou: Greetings. Welcome to The Nonprofit Exchange. We are into the fourth year of this now, Russ. Russ, I know we’re on an audio podcast, but I don’t see your smiling face. All I see is a picture. One of your better pictures.

Russell Dennis: Well, I’ll fix that. I should be live.

Hugh: There you are. I’m traveling today. I’m at a hotel in Orlando. We have a live audience here. We are going to be watching with bated breath, and we will come in with a few questions. We do have a little background noise, so I’m going to mute myself. It’s probably a popular notion with some people, so we will mute our end so it will be quieter. Russ has got some really good questions for what I think is going to be an amazing interview today with- Jess, you know me, so I am just getting acquainted with you. I am going to pay attention.

Jess Dewell: It’s great how that happened. You meet somebody, and they tell you all about you and how you think, yet you have never met them before because of the personality and the ways that we get to communicate. I totally understand being in that place.

Hugh: Love it. Tell us about yourself and how come you do what you do. Then Russell will take it on and ask you some really interesting questions.

Jess: That sounds great. I am Jess Dewell. I founded Red Direction 14 years ago. It started out as something slightly different than what it became. It became building frameworks for resilience. What came up on the radio show that I host, which was live streamed right before we are live streaming here, we were talking about bounciness. The more struggle we face, the more that we fall down, the more risks we are willing to take, we get bouncier. I love the concept of that and how that fits into businesses. Businesses can get that concept of bounciness. Pick ourselves up together, and go forward together. The last seven years have really been dialed into what we do for organizations that are growing and changing. They are in these critical points of development, and their leadership got them so far, their skills got them so far, and now it’s time to infuse them with more. Turn them upside down. Look at them in different ways to maximize the work flow, learning, and experience that already exists to go forward with grace and determination and whatever words you use to describe your companies. That is what we do over here at Red Direction.

Russell: It’s all about establishing the great culture. There are a lot of things that go into culture. For our audience, what does culture mean to you in the sense that applies to organizations?

Jess: You could look it up on the Internet and get the definition that Google or whatever your search engine is will tell you. I define culture as how we work together, and the strength with which we are able to work together and its effectiveness.

Russell: Yeah. What are some elements of culture that make organizations successful?

Jess: What makes an organization successful? I am getting cues that your volume, Russ, is not as high as our audience would like. Since I got that message, I am going to pass it on to you right here. Will you repeat the question?

Russell: What are some of the elements that go into culture that make an organization successful?

Jess: Are you ready for this? Are you really ready for this, Russ?

Russell: Bring it on.

Jess: People, people, people. There might be a few more p’s, and we will just replace them with people and people and people. It’s the culture. It’s what do we look at, how do we react, and preferably, how do we respond, and of course, how are the other people that we are surrounding ourselves with doing those things? And an awareness of the fact that we play off of each other.

Russell: Because you work with a lot of organizations of all types, what do you find are the biggest disconnects in organizations that have problems culturally?

Jess: Are you ready?

Russell: I am ready.

Jess: People, people, people, people, people. So really, it’s we think we are doing one thing, and we are being perceived as something different. There is a break in our communication. We think somebody is doing something, but we never actually asked the clarifying question. Even some people go, “I have a dumb question.” You know what? The dumb question that goes unasked just leads to bigger misunderstandings, so might as well ask that and get rid of the qualifier at the same time. “I have a question. Did I understand this right?” We are thinking of culture, and we are thinking of how to work together as a team. We all have different reasons for being in the roles that we are at. A wise man once told me, “The people who work here choose with their own two feet every single day to come to work for us.” I thought that was really a fabulous thing, and understanding that everybody has a different reason for being here, to work together. Yes, we have all agreed to this goal; however, if we haven’t created some sort of an awareness of how all of us fit into that end goal, we end up getting bumps and scratches and slowdowns and stalls and U-turns also.

Russell: Let’s look at the term “rules.” My good friend Dr. Hal Dibner talked with me the last time I saw him, we were actually talking about rules and how to move people to action. There are a lot of internal rules that each of us has that shapes the way we approach things and the way that we live. I think these rules can become internalized in the culture with an organization. What are some rules that you have seen that have become part of the culture of organizations that have hindered their progress?

Jess: I call those “elephants in the room.” The big elephants in the room. One of the things that Red Directions’ programs are really good at is finding the elephants in the room, pointing them out, setting up a little station, and inviting them to break them. Just being aware of what elephants are in the room. Another phrase might be “unwritten agreements.” We have done it this way. It’s worked all right, so this is the way that we do it. Whether that’s the case, or we are avoiding something, the elephants in the room, either way, when left unexplored, it can cause so many big problems. I have been a part of a company that has imploded because of that. I have also seen companies really unfortunately breed distrust and really feel fear around, “Am I actually safe in my role?” because of the unwritten agreements and insecurities and unknowns they cause. All that gets in the way of decision-making, which really when we are in business, is the ultimate goal: make decisions, nonprofit or otherwise, move toward an objective, make decisions, move toward an objective. Hit those goals and those signposts along the way.

Russell: I think that the way people view their work really impacts the culture. When organizations get stuck, in my experience, a lot of people don’t really like to be told what’s wrong. At what point do you find that organizations have hit a place where they are willing to have those conversations? How much does it generally take in your experience for somebody to reach that point?

Jess: It really varies. I have witnessed some other outlying symptoms if you will. If we were to look at symptoms that you are on your way down that rollercoaster, and you’re not sure if there is an up at the other side, is that everybody is tired. Everybody is behind. They are unable to keep up with the things that they have going on, with the commitments that they have made, and it becomes a drag. Those are the types of things that allow us to miss other cues. We are turned off from actually using our external perception, and it’s only stuck inside here. It can manifest other ways, too, besides the “I’m stuck,” “I’m overwhelmed,” or “I can’t meet my deadlines.” People leave. I’m burned out. People leave. “This is not what I thought it was going to be.” People leave, and then they are talking about their experience. They don’t talk about their experience until they leave. Nobody inside knew because there was a gap between each of the people, and there was “seemingly” to have a connection, but it was actually missing or had been broken.

Russell: A lot of our work focuses around leaders and how leaders interact and work with people and a common problem is leaders that overfunction.

Jess: Yes.

Russell: They take on a lot of things rather than train people. They find that it’s “quicker” just to do it myself than explain how to do it. Sometimes there is a fear of letting go of some control, not trusting people to do it. But if you bring people on to your team, you hire people because of the skills, knowledge, and abilities that will serve you, they have talent, and letting people actually do what it is that they do is a little difficult for leaders. That can get grounded in the culture. That creates burnout because you have a few high performers who are not being built to be better leaders, and they are just trying to do things instead of spreading them out, delegating, and building. The leadership skills of other people. We see that in nonprofits. Are you seeing that with-

Jess: In every organization. Every organization is susceptible to that. It’s interesting because yes, we hire for skills, knowledge, and ability. Most of the time, in most processes for bringing people on, what is left out, or what doesn’t have enough focus in that interview and onboarding process is what we mean when we say whatever we value. If service to a specific group, serving an underrepresented group in some way, if somebody comes on and they have the skills, the knowledge, and the ability, but they are only using this as a stepping stone, and they are exactly what you want for the job, part of the conversation becomes, “We know this is just a stepping stone on your path. Are you able to buy in? What do you like? What are we disconnected on what you’re doing while you’re here? Do you understand with where you’re going how this actually helps you get there?” You know what? A lot of people don’t want to face the fact that they are hiring someone who is going to leave. However, if we bring it up in the conversation, and we are talking about this, and it’s part of what we believe in, we know- We know we’re not going to do what we’re doing forever. We know we haven’t done what we’re doing forever. We have all had different experiences in the past. So why not just put that on the table? Then it’s never a surprise. Then it’s your performance reviews, your check-ins we’re having along the way, the conversations we are having before, after, and during meetings can still revolve around what are we doing in this organization? What is our mission? What is each of our parts in that while we are here? That type of collaboration is what is going to make somebody want to stay, but also it will prepare them to get them to where they want to go. As leaders, as employers, anybody with staff, it is our job to embrace and to love and get that person where they want to go because maybe this is the place, maybe it’s not, but we can do really well for them, for us, for our community, for our donors, for the people that we serve because of that small thing: having that type of conversation up front.

Hugh: Hey, Russell. We are having trouble hearing you.

Russell: It’s all about growth. That better? It’s all about growth. If you have a conversation about values, it’s important for both individuals and the organization to understand what it is that people want to get out of a relationship that you have. This is how you attract people, whether they are working for you, volunteering for you, coming to work as a staff member, coming to serve on your board. It’s having congruent values that will drive the day. The idea of growth is something that is fundamental to everything. To get better at what you do, you increase that level of support that you get. Culturally, with nonprofits, one of the things aside from the fact that you have some leaders that may overfunction, maybe they haven’t thought through all of their processes or systems or how they can actually get better at creating an experience because they are more effective and efficient at delivering their programs. Talk a little bit about your experience around that and some of the things that you would help people work around that.

Jess: I wouldn’t say work around, I would say work with and strengthen. The reason is that we all have a strength. When we can put a stake in the ground and say, “This is what I stand for,” wherever I work, whoever I work with, I know what I stand for in general. That allows me to have a guidepost when I show up in an organization and when I am working with other people. If other people are floundering around and are not sure, we put on that lens. What is important to me? What is my purpose here? What is my purpose in this situation? Maybe not my life purpose, but in this situation. How can I bridge that gap to move things forward? Those are the types of skills that we develop, programs that we create. The biggest reason for that is experience. Until we do it, we don’t know if we are good at it. Until we do it, we don’t know how to apply our personal strengths to the work that we’re doing. When we find our strength and can focus everything through that, it becomes easier as managers, as directors, to find the strengths in others and be curious and be willing to try a few things here to be curious with others to find their strengths as well. Maybe it’s a strength. A lot of people know that they can stay behind an idea. In a nonprofit, I come to work for a nonprofit, I volunteer at a nonprofit, I give money to a nonprofit because I care about the idea they are working on. When it comes to actually doing the infrastructure, taking the action to make all that possible-

You mentioned your values, how do we bring all of our skills together to get something done? But also you talked about processes and systems. Processes and systems are great on paper. As soon as you add people to them, you add what they are thinking in that moment, what their past was, what their dreams are, and what is on their mind right now in that situation. It may not be those things that are most important to working on an organization to develop it. Processes and systems are really impacted by all of the things that we care about, all of the things that we face. I am all about efficient systems, efficient processes. However, when we stop, when we weave what we care about, how we do our work together here at this organization, allows us to then be able to have a deeper conversation, a quicker conversation, which improves efficiency in a whole different way than just pushing the levers of a process.

Hugh: How about a question from Florida?

Danna Olivo: Yeah, Jess.

Jess: Bring it.

Danna: Bring it on. It’s funny that we’re talking about this today because- My name is Danna Olivo, and I am a business strategist. I work with early-stage micro-companies and medium companies. I work on those processes, the systems, and things like that. But one of the things that was really fascinating to me was you were talking about communication styles and hiring and things like that, talking about skills and values. One of the things that a lot of companies don’t take into consideration when hiring are the behavioral and cultural characteristics that are inbred in the people they are looking to hire and making sure that those cultural characteristics match the organization. Therefore, in order to do that, what we have done is we are trying to make a concerted effort to try and match those cultures to the behavioral characteristics to get a better understanding of their fit within the organization.

Jess: May I ask you a question?

Danna: Yes.

Jess: When you’re thinking about that, that means an organization really has to know.

Danna: The whole thing just dropped.

Jess: That means an organization has to really know where they stand. They understand that what they’re doing is already working. Do you find that a company is going to need some other help and some other work actually figuring out where they stand as an organization versus just being able to put this on top of what already exists?

Danna: Yes, I do find that part of the whole process is we have to make sure that they have those working systems and methodologies in place. Part of that process involves bringing the team on that will work with them in order to do that. If they aren’t centered around the same cultural values that the company has set in place, you are going to end up with a divided approach to these systems and methodologies. Does that make sense?

Jess: It makes complete sense. In fact, sometimes, in an existing organization that is going back, they are going, “We are having this problem hiring the right people. We are having this problem keeping the people we want who have the skills in our roles.” When we get to that, it’s interesting because people are always like, it’s the people. It’s the talent we are facing. They forget to look inward. Those would be the things where I’d be like, How strapped are ya? Because you might be better off having somebody do some temp work just for a short period of time, stop to take a step back, and evaluate some other things. Those are the elephants. You’re talking about the elephants in the room right there, Danna, and being able to recognize what we are willing to incorporate right now for where we are. One of the things that I hear in the work that you and I do, people want me to come in, and they think I can change everything. The answer is no, I can’t change anything. I can only facilitate and create a program to educate to allow that change to occur within an organization.

The other thing that people think, in all organizations, both profit and nonprofit, I get a lot of work done from people who have just done a rebrand, thinking that rebranding will actually solve the problems that we are unclear about what we stand for. You probably are unclear about what you stand for, but the way you look and describe yourself doesn’t matter. It’s a Band-Aid, isn’t it?

Danna: I love the fact that you’re talking about this because we are all about education. What I teach my people is you can’t operate in a vacuum. You don’t have all the answers. You have to surround yourself with that team that will be able to help you reach those goals. You have to surround yourself with those people who will be able to say, “You’re off base.”

Jess: I keep pointing with two different colored pens because these are the notes that I take. Anybody listening is going to be like, “What is she talking about?” I have two pens to take notes on every conversation that I have because there are things I want in one color and other things in another color. All of my notes have been written on before by a third color. If I hold up pens at you, it just means I’m excited. Yes!

Nonetheless, I hear what you’re saying. You’re right. It is about education. You said something that made me think about a program that we have. We talk about ThinkTime. This is a combination of words, think and time, that might be heard in the same sentence, that are squished together with no spaces. ThinkTime. This is something that we do at Red Direction. We have a process. How do I, as the steward of this mission that we’re on, whether it’s an entire organization, whether it’s a business unit, whether it’s my particular role, how do I in the stewardship of my position have time to actually allow all the chatter to get out? Because all that chatter has to get out to have new creative thoughts. More importantly, ThinkTime, a lot of people are like great. I like a whole day; however, I don’t use a whole day. I use a half day to get started. I use four hours, once a week for four hours, closing everything out. This is how that system typically goes. I am going to give you all the steps. You guys can play with this as much as you want.

That is first, put it in a calendar, and guard it fiercely. Four hours, one time a week. The first month, the first four, maybe the first eight, you are going to think they are useless. They will feel useless. All you will want to do is catch up on email. All you want to do is clear up the clutter on your desk. All you want to do is return those phone calls. All you want to do is write out a report that needed to happen or think about reports. It takes some time. But after about eight to ten sessions of four hours, all of a sudden, you sit down. I remember this so clearly the first time I did this. This is going to work; this is so great! You sit down, and it’s like, Okay, I actually see the Red Direction vision. I actually see the actions that we’re taking right now. I can just experience what that looks like and have an idea of what problems we’re facing right now, where we’re doing really well, and then what are the things that we could be doing better or different? When we have that space outside of our ThinkTime is when we go, Let’s break it down into a problem. Do I have a problem here? What’s that problem? Let’s go through those four steps of problem-solving. Then we can go bright. When we get to the options, we get to make a decision. Being confident in a decision comes from not running around rapid, not thinking or knowing we are never going to have all the answers no matter how much information you know about it, but we spent the time upfront to decide what the decision was, what the problem is we are going to solve. We are evaluating the path, not just a solution, but the path to betterment, the path to what we want next.

The more we get to do that, that’s the second piece, the more we get to practice those steps, the more confident we become in our decisions, and we can make them quicker. We can evaluate and get rid of options that don’t work right now.

Tell me this, Danna, and whomever is sitting next to you, and Russ. When you are sitting here and looking at all these problems you’re looking at all these things that are going on. I can choose any one of them. I don’t know what this means; you have too many options. Does that happen to you? Occasionally, sometimes, all the time.

Danna: Oh yes, even as a strategist, I find that I have to take a step back and decide, Okay, which one do I need to focus on right now? First of all. Secondly, what is the fastest way to come into a solution? By taking that step back sometimes and evaluating what is my talent, what is it, my talent that can help me come up with that solution? If I can’t find the talent within me to provide a solution, then I have a resource of people around me who I reach out to. I am not afraid to bring them in. You can’t operate in a vacuum. You said this. Our capacity as an entrepreneur only extends so far.

Jess: That’s right.

Danna: This happens to me. Jose Belen here, has a new nonprofit that he is starting called Mission Zero. Great nonprofit. We happen to be meeting Hugh here so we can get some tips and learn and stuff like that. Do you have any questions for her?

Jose Belen: No. Actually, this has been very informative. We have been around for about six months. Mission Zero is an organization dedicated to helping veteran suicide. That was part of the initial invasion into Iraq in 2003. Since I was honorably discharged in 2005, I have been fighting PTSD and suicidal thoughts. Every 80 minutes, there is a veteran somewhere in America committing suicide. We are dedicated to making a difference. So Mission Zero hopefully one day will stop veteran suicides. We appreciate any support and like-minded individuals. Thank you.

Danna: So they took the advice that you are giving. They have been surrounding themselves with the people who can help them get this off the ground rather than trying to do it all themselves.

Hugh: Jess, you probably know more about me than I know about you, but I’m quite amazed at the synchronicity of what you are talking about. I will give it back to Russell. I hijacked his questioning here. But it’s the synchronicity of what you are talking about and what we teach at SynerVision. This whole culture piece is core to transformational leadership and how we empower leaders. Thank you for such a passion around this. Love it. So, Russell, remember the old age and mental condition? I will give it back to you.

Russell: Almost escaped without that. He loves that one. That is his trademark thing. I don’t know why. It’s not true. He likes it. He entertains himself with that story. He’s going to find out as he gets to spend more time with you and learn more about you how remarkable you are. We haven’t known each other very long, but I love what you’re doing. What you’re talking about is creating safe spaces and collaboration. Collaboration is something that I think people are slowly starting to get. It’s a really important piece of everything that we do. It’s about people. I just had a mastermind this morning with other business leaders who were talking to me about helping me and my business. It doesn’t matter how many people you meet. A lot of times, there is that little piece of us that resists. Talk to us a little bit about how you help businesspeople, nonprofit leaders, some of the tools that you use to help them face that inner resistance. That is the one thing an organization, it’s all about people. We have this built-in resistance. Part of it is to change and some other things. Talk a little bit how you equip people to deal with that resistance and what they should look for.

Jess: Such a loaded question. There are like 212 ways—that is when water boils—we could start this conversation. I think ultimately the point is that water will boil. If we resist long enough, we have no choice, just like water in a pan on a stove. It doesn’t matter how long you leave it there. It will eventually reach 212 degrees and boil. I feel like when, so tools.

Let’s talk about tools. A lot of the tools that we teach are soft skills. The reason we teach soft skills is because I can come up with a process just like all of the other processes out there. Some would be good, and some would not be as good as the other ones out there. We all work differently. When we all work differently, and we are thinking about how we do what we do, we don’t give ourselves grace. We resist what our own strength is and how we work.

We are going to go back and use me as an example. There were five people in my family, three kids and two adults. Every Sunday, we would sit at the dining room table after dinner and we would look at the whole next week. If it wasn’t on the calendar, it did not happen. It was the time to ask questions, get permission, do all of this stuff. I grew up with this time management concept. I grew up with this concept of, Okay, we know who the decision-maker is, the person who can drive. If it doesn’t fit in their calendar, it can’t work, so I have to make a really good case that my stuff is more important than my sister’s.

This happens in business. This same thing happens in business. We get together, whether we are using time management skills or not, it comes down to how persuasive are we, how passionate are we? Can we clearly communicate the beginning, middle, and end of an idea to move it forward? Some people use time. I am really good at time and time blocking, and ThinkTime is a part of that. I am also really adept, and the programs we teach around soft skills are also around time management because we can only scale so much. We can only scale so much with one person. Each person can only scale so much. The whole purpose of being in an organization is to be able to understand what is my purpose, how do I leverage my time? What is their purpose, and how do we leverage their time? Have a good time doing it. Enjoy being together. You mentioned the word “ collaboration.” I think collaboration fits in a lot of different ways here. We are talking about- By the way, everybody who thinks collaboration- I am going to stop what I was going to say and talk about collaboration.

I have a bad taste in my mouth when somebody says collaboration because I remember when, and we can all do this, I remember a time I was on a collaborative cross-functional team, and I did all the work. Now you know- You’re a driver. You’re going to do what it takes. Right? So we have to let that go. Those of us who feel that way, and other people are like, Ooh, collaboration. I give ideas, give ideas, give ideas, and I don’t have to do anything. Let me just be an idea machine. Well, that only works to a point, too. Then there are the people who will take different kinds of action and throw in what some of us would call kinks in the wheel, but they are trying to make it better. They are poking holes in it. Can we get this to a point where we are seamless, we have something that can stick that we all agree on? Those people are really necessary, too. When we embrace not everybody does well, not everybody thinks well, not everybody wants to be the devil’s advocate, then we get to go, “Hey, we need everybody.” We can do this in a different way. We can have a conversation. Collaboration starts with a conversation. What are we doing? What can our parts be? How can we move this forward together?

Hugh: Jess, you have opened up a lot of topics.

Jess: I know, right?

Hugh: You’re in here because Russell invited you. I have to work hard so I can keep up with him. He’s a smart dude. What I’m going to throw out here is I’d like to take a couple of these themes and come back around and dig into some of these themes a little deeper. You have a whole lot of stuff to unpack here. We are coming to the top of the hour for this particular show. I want to talk about the sponsor moment here that makes it possible and give you a chance to wrap people’s heads around some of the major themes you want to leave us with. Then we will let Russell close us out. Does that sound good to you guys? Russ has been really diligent in helping us pull this together today with a whole lot of technical issues.

*Sponsor message for Rock Paper Simple*

Jess, how would you like to wrap this up and leave folks with? What is a profound thought you want to leave people with before Russ closes out this great session?

Jess: All right, we just upped the ante. The most profound thought you want to leave us with, Hugh. There is no low bars here. Everybody, I have listened to a few of these in preparation for this conversation. Of course, I know Hugh, and I know Russ. There is no going back; there is only forward. I think that that’s really a key piece of what culture and what we’re talking about when we are talking about these elements of culture is that we are always moving forward. We can embrace it. We can resist it. Either way, it’s coming. We can make it more fun. We can make it more effective, and we can serve more people when we get out of our own way and we recognize our own self and how we can show up and invite others to continue to join our party.

Russell: Great stuff. In conversation with what’s happening with anything that I touch has to start in the mirror. That is the X factor. That is the one thing I can actually do something about. The willingness to actually look at where we are as individuals energetically makes a big difference. We can find some compassion for ourselves in there and in other people and put ourselves in their shoes and say, “How can we create an experience? How can we get to the larger point? What are the things we need to put on the shelf to make this thing work the way it is built to work?” That is really where it starts.

Jess, as always, it’s been a pleasure. Danna, Hugh, all of our friends down at CEO Space, the July forum, wonderful organization. Being a part of that has changed my life. I have a contact in veteran suicide that is actually somebody that has been in Texas shining the spotlight on it. His primary thing is to get their stories captured. We will cycle back around and talk about that again.

In the meantime, I’d like to thank all of our listeners out there every week who join us here at The Nonprofit Exchange. We got a really good guest next week. He is going to be talking about conversations. He has an incredible tool that can help us look at the way we have conversations on a personal and professional level. You don’t want to miss this because he has got a brilliant tool called Conversations. Join us next week for that. Hugh.

Hugh: Thank you, Russ. Thank you, Jess. It’s been a great session. Thank you so much.

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