Leaving Well Podcast - The Final Season: What Nearly 100 Conversations Taught Me About Leaving Well
After four seasons and nearly 100 episodes, I'm closing the Leaving Well Podcast. Not because the work is done—it's not. But because seasons end, and this one is ready to do just that.
Over the next several months, I'll release the final Season 4 episodes. These conversations with leaders and experts carry the same clarity, care, and courage that made me fall in love with hosting this podcast in the first place. But before we get to those, I want to share what this journey has taught me about the very thing I set out to explore: Leaving Well.
What We Talked About (And What Really Mattered)
When I launched this podcast in September 2023 with a conversation with Shannon Watts, the founder of Moms Demand Action, I knew nonprofits needed different conversations about transitions, and leaders needed to hear different examples of leaving well. We've spent decades pretending people don't leave, then we scramble when they depart, and end up losing institutional knowledge we can't afford to lose.
In those episodes, here's what emerged:
People Leave. Full stop. The average nonprofit ED tenure is now six years, down from ten. Sixty-seven percent of nonprofit executives plan to leave within five years. We can keep acting surprised, or we can build systems that expect and honor transitions. The guests on this podcast—from interim executive directors to organizational psychologists to founders closing their organizations—showed us what the latter looks like. Expecting and honoring transitions.
Grief belongs in leadership conversations. Dr. Jaiya John taught us that workplace culture is a garden requiring constant tending. When we ignore the grief that accompanies change, we're letting weeds overtake the entire ecosystem. Several guests - including Kemi Ilesanmi - named what most organizations avoid: transitions involve loss, and pretending otherwise doesn't make you stronger or a better leader—it makes you dishonest.
Interim leadership is strategic, not stopgap. Joan Brown, Ingrid Kirst, Katie Mendez, and others helped reframe interim roles from "we're desperate" to "we're intentional." Bringing in a professional interim isn't admitting failure. It's acknowledging that leadership transitions require specialized skills—skills that support knowledge continuity, protect your bottom line, and position your next leader for success.
How you leave shapes your legacy more than how long you stay. I used to agree with the societal norm that long tenure equals transformational leadership. Nearly 100 conversations corrected that assumption. Your final act of leadership—the graceful transfer of authority—may be your most consequential. It determines whether your successor inherits a mess or a foundation. It also determines how seamless the continuation of the organization’s mission can be.
Rest isn't a luxury or a reward. It's infrastructure. Multiple guests emphasized that sabbaticals, actual time off, and energy conversations shouldn't be reserved for the exhausted. They should prevent exhaustion. Organizations that embed rest as a core value rather than a perk create cultures where people can leave well—or choose to stay.
Conscious closures matter. Camille Acey's work on conscious nonprofit endings challenged our field's assumption that every organization must exist in perpetuity. Sometimes the most responsible thing a board can do is sunset the nonprofit organization, and close well. That requires the same intention, planning, and care as any other transition—maybe more.
The Patterns That Emerged
Season 1 brought guest stories. Season 2 introduced the Leaving Well framework. Season 3 featured game changers and colleagues’ wisdom in this work. Season 4 delivered expert insights and framework deep-dives.
Across all four seasons, three patterns showed up repeatedly:
Organizations in crisis mode make terrible transition decisions. Every single guest who discussed failed transitions pointed to reactive realities, rather than proactive planning. Boards are left to scramble and fill vacant ED roles, teams promote internal candidates without interim support, and founders leave without succession plans..
The best transitions honor both past and future. Guests who left well didn't trash their organizations on the way out, but also didn’t pretend everything was perfect. They named what worked, acknowledged what didn't, and created space for what's next. That's the work.
Culture either supports leaving well or punishes it. Some guests described workplaces where announcing your departure meant immediate exile—no goodbye gatherings, no knowledge transfer, no acknowledgment. Others agree with my love for stay interviews, proactive succession planning, and celebrations of people's next chapters. Guess which organizations retained institutional knowledge and attracted top talent?
Why You Can't Do This Alone
Organizations that try to handle transitions internally, without external support, consistently make preventable mistakes. And boards that think they can DIY succession planning end up scrambling when their ED gives notice.
In Episode 51, I laid out why interim executive leadership requires professional expertise—not just a willing board member stepping in. It’s so tempting as board members know the organization, care about the mission, and have some institutional knowledge. Perfect interim candidate, right? Wrong. Board members serving as interim staff create governance nightmares, blur accountability lines, and often can't provide the objective assessment a transition requires. Professional interim leaders bring specialized skills: stabilizing chaos, protecting institutional knowledge, assessing what's actually happening (versus what the board thinks is happening), and positioning the organization for its next permanent leader.
The data backs this up. Organizations that bring in professional interim support experience significantly less productivity loss during transitions. They retain more staff. They onboard permanent leaders more successfully. Interim work isn't just "keep the lights on"—it's strategic intervention during a vulnerable moment.
Episode 40 tackled a different angle: protecting your own heart when you're the one leaving. This is where external support becomes personal rather than organizational. Too many leaders I've worked with tried to navigate their departures alone—managing their own grief, their team's reactions, their board's anxiety, and their uncertainty about what's next. Simultaneously and without support. That's not strength, it’s instead a recipe for burnout, regret, and departures that damage everyone involved.
External coaches, consultants, and thought partners create space for you to process what's actually happening. They ask questions your team can't ask, and give you permission to acknowledge that leaving something you built feels like grief—because it is. They help you distinguish between "I'm having a hard week" and "this role is no longer serving me or the mission." Without that external perspective, leaders stay too long, leave too abruptly, or exit without the closure that honors what they contributed.
In Episode 77, I delivered what I called a "podcast-style keynote" on the reality that People Leave™. This solo episode synthesized patterns I'd seen across the seasons of conversations and the last years of client work. Only 27% of nonprofits have written succession plans. Nearly three-quarters of organizations are operating without proactive transition strategies. When a leader departs, these organizations scramble. They make rushed decisions driven by panic rather than strategy. Then they wonder why the transition destabilized everything.
You cannot see your own organization's blind spots.
You cannot objectively assess your readiness for transition when you're inside the system.
You cannot facilitate your own departure and manage everyone else's feelings about it.
Boards cannot effectively plan for succession without external facilitation—too many competing interests, too much organizational history, too little distance from the day-to-day.
The guests who shared the healthiest transition stories consistently mentioned external support. Consultants who helped boards develop succession plans before they needed them. Executive coaches who helped departing leaders process their decisions. Interim directors who stabilized organizations so permanent leaders inherited functional systems instead of crises. Search firms that brought rigor to hiring processes. Organizational development experts who helped teams navigate grief and change.
This isn't about organizations being incapable. It's about transitions requiring specialized expertise that doesn't typically exist internally. Just like you shouldn’t ask your board treasurer to conduct your financial audit (conflict of interest, lack of independence), you shouldn't ask internal stakeholders to facilitate major transitions without external support.
The cost of bringing in expertise is small in comparison to the following costs:
botched transitions
failed searches
prolonged vacancies
knowledge attrition
demoralized staff
damaged reputations
legal risks from poorly managed departures
These aren't hypotheticals—this is reality.
Leaving Well requires support. Whether you're the person leaving, the board managing the departure, or the organization navigating change, external expertise isn't a luxury. It's infrastructure.
“The organizations that invest in Leaving Well don’t just survive transitions—they use them as opportunities to strengthen, clarify, and grow.”
What I'm Taking With Me
This podcast gave me the gift of learning from people doing hard things with integrity. I so enjoyed the conversations with leaders who left organizations they loved because staying would compromise their values. It as joyful to talk to fellow interim directors who stabilized chaos and then stepped aside. It was reassuring to hear from founders who closed and sunsetted nonprofits because the need had shifted or to pass along programming to a partner org. And beautiful to chat with vulnerable board members who admitted they weren't prepared for leadership transitions and did the work to change that.
Every conversation reinforced what I teach in my consulting and advisory practice: leaving well benefits everyone. It mitigates productivity loss, builds company loyalty, protects your reputation and your team's wellbeing, and … creates pathways for growth—yours and theirs.
Why Now
You might wonder why I'm closing a podcast that's resonating with its audience and generating meaningful conversations. The answer is the same reason I encourage clients to leave roles before burnout forces them out: I can feel the shift. My energy is pulling toward other projects. My client work is deepening in ways that require more focus. And I'm practicing what I preach—leaving while there's still love and intention, rather than waiting until I resent the commitment.
I also know that the Leaving Well framework doesn't need a podcast to survive. It needs leaders like you implementing it in real time with your boards, your teams, and your own career transitions. The nearly 100 episodes we've created - together - aren't going anywhere. They'll remain a resource for anyone navigating change.
What Happens Next
Over the coming months, Season 4's final episodes will release. These conversations deserve your attention:
Leaders discussing the intersection of succession planning and equity
Experts breaking down why most transition plans fail and how to build ones that don't
Real stories about walking away from toxic workplace cultures and protecting your heart in the process
Deep dives into the Leaving Well framework's key components
After the final episode releases, I'll keep doing the work that matters most—partnering directly with nonprofits on interim leadership, succession planning, and building cultures where transitions aren't crises.
A Practice, Not a Proclamation
Leaving well isn't about perfect exits or conflict-free transitions. It's about approaching endings with the same care and intention you bring to beginnings. It's about recognizing that change is guaranteed and trauma is optional. It's about understanding that 100% retention is neither realistic nor healthy.
Every guest on this podcast demonstrated some version of this truth. They left jobs that weren't serving them. They closed organizations that had completed their missions. They supported leaders through transitions instead of pretending departures wouldn't happen. They grieved what was ending and made space for what was beginning.
That's the work. And it's work worth doing.
Thank You
To every guest who shared their story: you gave this podcast its heartbeat. Your willingness to be honest about the messy, difficult, beautiful process of leaving well created permission for thousands of listeners to do the same.
To everyone who listened, shared episodes, and reached out to say "I needed to hear this": you reminded me why this work matters.
And to those of you navigating transitions right now—whether you're leaving, staying, or somewhere in between: may you find in these conversations the same clarity, care, and courage that hosting them gave me.
Seasons end. This one is closing. And I'm leaving it well.
The Leaving Well Podcast launched September 6, 2023, and will conclude with final Season 4 episodes releasing over the next several months into early 2026. All episodes will remain available on your preferred podcast platform and here on our website. For support with nonprofit leadership transitions, interim executive leadership, and succession planning, contact us.