About a decade ago, I helped a once multimillion-dollar nonprofit with about 50 employees close its doors, and before it was over, board members wrote personal checks to cover money owed to the IRS. In this episode, I share the five lessons I took from that work. And these lessons are essential for chief executives and board members alike: keep a cash flow projection, cut staff or expenses long before payroll is at risk, treat your audit and government filings as sacred deadlines, never let your directors and officers insurance lapse, and watch for the small missteps that add up to insolvency. I also answer a question from the live audience about whether cutting staff actually keeps an organization open, and share a free cash flow projection template to get you started. You can get my free cashflow projection template at www.successfulnonprofits.com/cashflow This episode answers questions like: How do I know if my nonprofit is headed for financial trouble? What should I do if I'm worried we won't make payroll? When should a nonprofit lay off staff to stay afloat? Can we pay employees their net checks now and catch up on payroll taxes later? Should our nonprofit use a line of credit to get through a cash shortfall? Links mentioned in this episode: Free cash flow projection template: https://successfulnonprofits.com/cashflow/ Board retreats and board development: https://successfulnonprofits.com/build-the-board-you-need/ Executive coaching for nonprofit chief executives: https://successfulnonprofits.com/individual-coaching/ Curious about a board retreat or executive coaching? Contact me using the contact form: https://successfulnonprofits.com/contact-us/ Looking for more? Check out these other amazing episodes: How to Deliver Bad News to Your Board Without Losing Trust: https://successfulnonprofits.com/deliver-bad-news-nonprofit-board/ The CFO Crash Course with Tosha Anderson: https://successfulnonprofits.com/portfolio/the-cfo-crash-course-stepping-up-your-nonprofits-accounting-game-with-tosha-anderson/ Top 5 Mistakes Nonprofit Executive Directors Make with Marvin Webb: https://successfulnonprofits.com/portfolio/top-5-mistakes-nonprofit-executive-directors-make/ Join the live virtual audience for podcast recordings (and bring your question for the Q&A). Topics, guests, and times are announced in my newsletter, and you can sign up at this link: https://successfulnonprofits.com/newsletter-signup/

When your organization's biggest fundraising event is on the line, where should the chief executive lead, and where should she stay out of the way? Jai Ferrell, CEO of Girl Scouts of Greater Atlanta, transitioned a long-running luncheon in her first year to a gala that raised more than $500,000. In this episode she explains who should make an ask, how to choose honorees, and how she spends every minute of the event itself, including the "wrangler" who keeps her moving. If your event depends on you and you are not sure what that should mean, this conversation gives you a clear division of labor between you, your team, and your board. This episode answers questions like: What should an executive director do at a fundraising gala? Should I make every sponsor ask myself or ask team members or board members to do some? How do we choose honorees for a nonprofit gala? Should we replace our fundraising luncheon with an evening gala? How can a nonprofit host a gala without spending significantly more on the event? What does a nonprofit CEO do at a fundraising event? How do I get out of long and unproductive conversations at my own fundraising event? Links mentioned in this episode: Girl Scouts of Greater Atlanta: https://www.girlscoutsatl.org/ Jai Ferrell on LinkedIn: https://www.linkedin.com/in/jaiferrell/ Expect to Win by Carla Harris: https://www.penguinrandomhouse.com/books/303288/expect-to-win-by-carla-a-harris/ Looking for more? Check out these amazing episodes: Are Fundraising Events Worth Your Time? A 10-Hour-a-Month System with Mary Thompson: https://successfulnonprofits.com/portfolio/are-fundraising-events-worth-your-time/ Your Board's Fundraising Retreat: 6 Ways to Make It Count: https://successfulnonprofits.com/fundraising-board-retreat/ Join the live virtual audience for podcast recordings (and bring your question for the Q&A). Topics, guests, and times are announced in my newsletter, and you can sign up at this link: https://successfulnonprofits.com/newsletter-signup/

Join the live virtual audience for podcast recordings (and bring your question for the Q&A). Topics, guests, and times are announced in my newsletter, and you can sign up at this link: https://successfulnonprofits.com/newsletter-signup/ Whether or not you like AI, you are already using it, from spell check to your social media feed. Yet most nonprofits have barely put it to work where it could give leaders time back. In this episode, I share six roles AI can play in a small or mid-sized nonprofit without significant new spending: admin support, IT support, research, marketing, finance, and management systems. Every example comes from real use, from a scheduling agent that coordinated five time zones to a monthly website scan that caught about a hundred typos. I also cover how to check a 990 before you sign it, how to respond to audit findings with policies that fit your actual staff, and why none of this works without clear instructions and supervision. This episode answers the following questions: How can a small nonprofit use AI without a big technology budget? What administrative tasks can I hand off to AI? Can AI help our finance office if we don't have a CFO? How do I research a donor or board prospect before a meeting? How can AI help me prepare for our nonprofit audit? Should I have AI review our 990 before I sign it? How are other nonprofits using AI to save staff time? What should a nonprofit consider before using AI with confidential information? Links mentioned in this episode: Free online training, Design an AI Strategy That Builds More Capacity (October 14, 2026, 1:00 p.m. Eastern): https://successfulnonprofits.com/trainings/ Curious about executive coaching? Contact me using the contact form: https://successfulnonprofits.com/contact-us/ Subscribe to the newsletter and join a live podcast recording: https://successfulnonprofits.com/newsletter-signup/ Looking for more? Check out these other amazing episodes: Stop Doing $25-per-Hour Work: https://successfulnonprofits.com/stop25work/ The CFO Crash Course with Tosha Anderson: https://successfulnonprofits.com/portfolio/the-cfo-crash-course-stepping-up-your-nonprofits-accounting-game-with-tosha-anderson/ The One Spreadsheet Every Nonprofit Manager Needs: https://successfulnonprofits.com/nonprofit-task-checklist/

A staff member unhappy with one of your decisions skips you and goes straight to the board chair. If the chair entertains it, your ability to lead takes a hit that is very hard to repair. In this episode I share when this happened to me as a chief executive, as well as what I've learned about responding in a way that strengthens the organization's effectiveness and my leadership. I also cover four ways to future-proof your organization, from a written plan with your board chair to a validated staff engagement survey, and four traps that look like solutions but aren't. Chapters: 00:00 When staff go around you to the board 01:24 The three moments it tends to happen 02:38 The first time: brought in to right the ship 05:47 The call on the last night of the conference 09:34 The second time, and my resignation 10:46 The third time, as an interim executive director 15:09 Three meetings to repair the damage 20:37 Four ways to future-proof your organization 26:07 Four traps that look like solutions 29:13 Homework, and what to do if it is happening now This episode answers the following questions: What do I do when a staff member complains about me to the board? Should my board chair meet with my staff without telling me? How do I stop employees from going around me to the board? When should staff go directly to the board of directors? How can a nonprofit board measure staff morale without undermining the executive director? Should my nonprofit use a 360-degree evaluation to evaluate me as executive director? What do I do when my board chair has undermined me with my staff? Links mentioned in this episode: Gallup's Q12 Employee Engagement Survey: https://www.gallup.com/q12-employee-engagement-survey/ Curious about executive coaching or board retreat facilitation? Email me using the contact form Subscribe to the newsletter and join a live podcast recording: https://successfulnonprofits.com/newsletter-signup/ Looking for more? Check out these other amazing episodes: Stop Being Your Team's Referee Building Strong CEO-Board Chair Relationships with John Fulwider The Supportive Board Chair with Monica Khant Join the live virtual audience for podcast recordings (and bring your question for the Q&A). Topics, guests, and times are announced in my newsletter, and you can sign up at this link: https://successfulnonprofits.com/newsletter-signup/

A staff member knocks on your door and asks you to settle a disagreement with a coworker. Saying yes feels good, and it is one of the few things in your week that ends cleanly. It also teaches your team to bring you every dispute, and it pushes the fundraising, board, and strategy work that only you can do into your nights and weekends. In this episode I walk through escalate together, a practice I draw from Kim Scott's Radical Candor and use in every interim executive director engagement. Staff make a good faith effort to work it out themselves, and if they are still stuck, they come to me together. I cover how to set up the room, the two questions I ask once everyone sits down, the issues that belong in formal channels instead, and what to do about the frequent flyer who has escalated with eight different colleagues in a year. You will also hear what happened when I rolled this out on my first day at an organization with a long history of instability, and a team member knocked on my door about 90 minutes later. This episode answers the following questions: How do I stop my staff from bringing me every disagreement? What do I say when an employee complains to me about a coworker? Is it the executive director's job to mediate conflict between staff? How do I get my team to resolve conflict without me in the room? When does a staff complaint go to HR or an attorney instead of to me? How should a nonprofit CEO handle an employee who has conflict with everyone? Does any of this work with a fully remote team? How do I roll out a new management practice to my board chair and my staff? Links mentioned in this episode: Radical Candor by Kim Scott: https://www.radicalcandor.com/the-book (also on Bookshop.org) CEO Excellence by Carolyn Dewar, Scott Keller, and Vikram Malhotra: Bookshop.org The Netflix culture memo, where the team and not a family framing comes from: https://jobs.netflix.com/culture Curious about executive coaching, including the coaching library I send new clients? Contact me. Subscribe to the newsletter and join a live podcast recording: https://successfulnonprofits.com/newsletter-signup/ Looking for more? Check out these other amazing episodes: Conflict Can Be Good for Your Organization with Nate Regier The First Four Words: Starting Conversations with Confidence with Tucker Miller Timeless Tips for Working with Difficult People with Jody Foster Join the live virtual audience for podcast recordings (and bring your question for the Q&A). Topics, guests, and times are announced in my newsletter, and you can sign up at this link: https://successfulnonprofits.com/newsletter-signup/

Most executive directors put off planned giving because it feels like a time consuming and expensive project that requires a consultant, a gift acceptance policy, board training, a recognition society, and more. And after investing so much into planned giving, you won't receive a gift for years. Tony Martignetti has spent 29 years proving that belief is just not true. In this episode he walks us through his three-step, one-week launch; explains why three or four top prospects is a real planned giving program; and dismantles the objections that keep chief executives from closing the simplest gift there is (and the easiest one to ask for). We also get honest about what stewardship of your planned giving donors actually costs. If you are the CEO who wears many hats, this is the fundraising conversation that pays off long after your current grant cycle closes. This episode answers questions like: How do I start planned giving without a development director? Do we need a gift acceptance policy before we can ask for bequests? How many planned giving prospects can an executive director realistically handle? How do I identify planned giving prospects? When do I tell my board about a planned giving program? Is planned giving worth it for a small nonprofit with a tight budget? What do you say to a board member who is worried about a donor leaving us property we'll never be able to sell (like a toxic waste site)? How do I steward and cultivate planned giving donors over the long term? Links mentioned in this episode: Tony's book, Planned Giving Accelerated, plus a free chapter: https://plannedgivingaccelerated.com/ Planned Giving Accelerator: https://plannedgivingaccelerator.com/ Tony Martignetti Nonprofit Radio: https://tonymartignetti.com/ The Millionaire Next Door by Thomas J. Stanley and William D. Danko: https://bookshop.org/p/books/the-millionaire-next-door-the-surprising-secrets-of-americas-wealthy-thomas-j-stanley-ph-d/d2115bc2d7f2d07c?ean=9781589795471 Subscribe to the newsletter and join a live podcast recording: https://successfulnonprofits.com/newsletter-signup/ Join the live virtual audience for podcast recordings (and bring your question for the Q&A). Topics, guests, and times are announced in my newsletter, and you can sign up at this link: https://successfulnonprofits.com/newsletter-signup/

If you're in the chief executive seat long enough, something will eventually go wrong. A cash-flow crisis, the loss of a key funder, a serious audit finding, critical news coverage, or an on-site disaster can test both your leadership and your relationship with the board. In this episode, I lay out a practical way to deliver bad news to your board without creating a second crisis. I share who to tell first, the six questions your written board update must answer, and how to structure an emergency meeting so the loudest board member does not control the conversation. You will also learn when to stop weekly updates to your board and how to conduct a post-mortem after the issue is fully resolved. The central lesson is simple: bad news does not break trust, but surprise, avoidance, or inaction will.

If you are a CEO responsible for moving your mission forward in a polarized environment, this conversation will sharpen how you lead. Your ability to communicate with people who don't share your or your nonprofit's values and views can determine whether your organization gains traction or stalls out. In this episode, I speak with consultant and former executive director Chandra Brown about how leaders choose words and framing that build alignment with board members, donors, policymakers, and community stakeholders. You'll hear a real-world example of a messaging misstep that backfired and what it reveals about how different audiences interpret the same issue. You'll walk away with practical ways to communicate across political divides without compromising your values. This episode answers the following questions: How do executive directors communicate with stakeholders who disagree with them? How can I get board members or donors to support an issue they're skeptical about? What's the best way to talk about controversial issues without alienating my supporters? How do I build alignment across my nonprofit's politically divided constituencies? How do I prepare for conversations with policymakers who oppose my position? Links mentioned in this episode: Influence Advocacy (Chandra Brown). Influence Advocacy and Chandra can give your issue a helping hand using data driven strategies that support your issue campaigns.

Can one board retreat turn reluctant board members into fundraising superstars? Anyone promising that is selling something they cannot deliver. But a well-designed retreat can still move board fundraising forward. In this episode, I explain how to diagnose the real barriers first, then share six practical retreat activities that can help a board align expectations, understand its fundraising options, practice useful skills, map its networks, and make specific commitments. I also outline the post-retreat work that turns your board members' commitments into results. This episode answers the following questions: Can a board retreat actually get board members to fundraise? Why is my nonprofit board not engaged in fundraising? What fundraising activities can we use at a board retreat? How do we set and enforce fundraising expectations for board members? What should staff and board leadership do after a fundraising retreat? Links mentioned in this episode: Bring Dolph into your next board retreat. I design and facilitate board retreats that are interactive, practical, and built around the board's real barriers. Retreat topics can include fundraising, governance, board evaluation, planning the board's work, crisis or contingency planning, and strategic planning. To discuss your next retreat, reach out to me at successfulnonprofits.com.

What recurring tasks does each person on your team actually own? It's almost impossible to remember everything a team member is responsible for, and a job description usually won't tell you. When that information lives only in someone's head, onboarding gets harder, performance conversations get murkier, and an employee departure can create unnecessary chaos. In this episode, I share my simple, one-tab staff task checklist I use when leading nonprofit teams. It documents each position's recurring work and how often it needs to happen. It also becomes a practical tool for interviewing candidates, onboarding new employees, managing performance, cross-training staff, reviewing job descriptions, and being ready for staff departures. You'll also learn how this simple exercise can expose tasks only one person knows how to do, processes that still lack documentation, and responsibilities that have quietly changed over time. This episode answers the following questions: How do I keep things from falling through the cracks when an employee leaves? What should I document before a key employee quits? How do I onboard a new employee without constantly answering questions? How do I know if important tasks depend too much on one employee? How do I hold staff accountable when responsibilities aren't clear? How do I cross-train employees at a small nonprofit? How do I update job descriptions when staff roles have changed? Links mentioned in this episode: The checklist in an editable Excel format: https://successfulnonprofits.com/checklist Free Online Trainings for Nonprofit CEOs: https://successfulnonprofits.com/trainings/ Looking for more? Check out these amazing episodes: Why Our Team Members Fail with Dr. Tiffany Slater 12 Ways You Can Recruit and Retain Top Talent Stop Doing $25-per-Hour Work