After 100 Conversations About Leaving Well, Here's What Actually Matters


After four seasons and nearly 100 episodes, I'm closing the Leaving Well Podcast. Not because the work is done—far from it. But seasons end, and practicing what I preach means leaving while there's still intention and love for the work.

The final Season 4 episodes will release over the coming months. But first, I want to share what this journey taught me—and what it means for your organization's next transition.

What 100 Leaders Taught Me

When I launched in September 2023, I knew nonprofits needed different conversations about transitions. We spend decades pretending people don't leave, then scramble when they do, losing institutional knowledge we can't afford to lose.

Here's what emerged:

People leave. Full stop. The average nonprofit ED tenure is now six years, down from ten. Sixty-seven percent of executives plan to leave within five years. You can keep acting surprised, or you can build systems that expect and honor transitions.

Grief belongs in leadership conversations. Transitions involve loss. Pretending otherwise doesn't make you stronger—it makes you dishonest. The leaders who navigated transitions best acknowledged this reality instead of bypassing it.

Interim leadership is strategic, not stopgap. Bringing in a professional interim isn't admitting failure. It's acknowledging that transitions require specialized skills—skills that protect your bottom line and position your next leader for success.

How you leave shapes your legacy more than how long you stay. 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.

Rest is infrastructure, not luxury. Sabbaticals and actual time off shouldn't be reserved for the exhausted. They should prevent exhaustion. Organizations that embed rest as core value create cultures where people can leave well—or choose to stay.

Three Patterns That Showed Up Repeatedly

  1. Organizations in crisis mode make terrible transition decisions. Every failed transition started with reactive scrambling rather than proactive planning.
  2. The best transitions honor both past and future. They name what worked, acknowledge what didn't, and create space for what's next.
  3. Culture either supports leaving well or punishes it. Organizations that celebrate transitions, conduct stay interviews, and plan proactively retain institutional knowledge and attract top talent. Those that exile departing leaders lose both.

Why You Can't Do This Alone

Here's the truth: you cannot see your own organization's blind spots. You cannot objectively assess transition readiness when you're inside the system. You cannot facilitate your own departure while managing everyone else's feelings about it.

Only 27% of nonprofits have written succession plans. Nearly three-quarters are operating without proactive transition strategies. When leaders depart, these organizations scramble and make rushed decisions driven by panic.

The guests and experts on the podcast who shared the healthiest transitions 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, not crises
  • Search firms that brought rigor to hiring processes

This isn't about your organization being incapable. It's about transitions requiring specialized expertise that doesn't typically exist internally. The cost of external support is minimal compared to the cost of botched transitions, failed searches, prolonged vacancies, knowledge attrition, demoralized staff, and damaged reputations.

Why I'm Closing Now

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 (like online cohort spaces for nonprofit leaders, and full day succession planning retreats with a group of grantees). My client work is deepening in ways that require more focus.

I'm practicing what I preach—leaving while there's still intention, rather than waiting until I resent the commitment.

The Leaving Well framework doesn't need a podcast to survive. It needs leaders like you implementing it in real time with your boards, teams, and career transitions.

What This Means for You

If you're navigating a transition right now—whether you're leaving, managing someone's departure, or building proactive systems—the work matters. And you don't have to do it alone.

All episodes remain available on your preferred podcast platform and at naomihattaway.com. For direct support with nonprofit leadership transitions, interim executive leadership, and succession planning, reach out.

Seasons end, and this one {the podcast} is closing well.

Gravel Road, Chattahoochee Hills, GA 30213
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Leaving Well in the Workplace

Your Leaving Well guide to navigating workplace transitions 🧡 I normalize workplace transitions one organization + person at a time. Leaving Well is the art + practice of leaving in the workplace, with intention + joy.

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