673. Shift 3 — People Leave: Make Transition Readiness Part of Your Culture - Naomi Hattaway
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This episode is part of 12 Shifts in 2026 for Social Impact.
Overview
People Leave™ — and in 2026, the pace and intensity of transition is accelerating. In this episode, Naomi Hattaway, interim leader and organizational health builder, shares what it actually takes to build nonprofit health through uncertainty before someone resigns. We talk about the hidden fragility that uncertainty exposes (founder dependency, undocumented roles, disengaged boards), and the practical foundations that help teams stay aligned when everything feels on fire.
You’ll walk away with concrete tools for transition readiness, including how to:
Treat turnover as normal — not a crisis — so you plan for departures instead of getting blindsided
Build real financial resilience with reserves and budgets that account for searches, interims, and transition support
Create simple documentation so critical knowledge isn’t trapped in one person’s head
Grow “endings literacy” by talking openly about departures, loss, and what it means to leave well
Center humanity in hard moments with grief-aware practices, dignified layoffs, and stay interviews
Because healthy systems don’t stop people from leaving — they make it possible for people to leave well.
Homework:
Naomi’s One Good Thing + Homework:
90-Day Focus: Document one critical role function as if its owner just won the lottery and said "peace out." Deliver scrappy, operational "here's how" steps—no nonprofit jargon. Use screen recordings (many auto-generate SOPs) for easy functions first. Bonus: Announce you're doing this and invite your team to pick one function each.
Year-Ahead Shift: Normalize endings conversations. Add "strategic sunset scenarios" or "landscape analysis" to quarterly board agendas—not to plan closure, but to sharpen present decisions through future possibility.
Naomi’s 4 Must Haves for the Year:
Honest Infrastructure
Document via recordings of tasks, relationship maps (who matters, why, contacts), brain dumps, transition memos (wins, stuck points, pending decisions), and drafts reviews.
Endings Literacy
Discuss board terms and past exits (rights/wrongs, team responses); prioritize stayers and open conversations about departures.
Financial Truth-Telling
Budget for transition costs like searches, interims, stipends, severances, and delays; establish reserves policies.
Distributed Knowledge
Spread info beyond individuals using scrappy docs, Looms, or notes to prevent single points of failure.
Dive Deeper:
“If I win the lottery tomorrow, how do I want to leave my work to someone else?”
Episode Transcript
Download Full Episode Transcript Here
Episode Highlights
Understanding Uncertainty in 2026 (02:06)
Proactive vs Reactive Approaches (05:39)
4 Must Haves for this Year (5:26)
The Importance of Infrastructure (07:54)
Endings Literacy: Navigating Transitions (13:30)
Creating a Culture of Grief and Loss (22:00)
Leaving Well: The Art of Transition (28:26)
Human-Centered Change in High-Stress Environments (31:25)
Naomi’s One Good Thing (35:07)
Powerful Quotes
“What can you do today that is good for you, your organization, your community, and your team?” -Naomi Hattaway
“Plan as much as you can around what it looks like if and when you end can help you make honest decisions about today and your present.” - Naomi Hattaway
“Truth tell with compassion. Speak openly and transparently about what is going on.” - Naomi Hattaway
“How would you ever want to leave your legacy or the mission of your organization without documenting what’s in your head?” - Naomi Hattaway
“If I can do my part to leave an organization better than I found it, to me that is something that doesn’t need to have a leader stamp of approval.” - Naomi Hattaway
“Holding space for grief and holding space to talk about loss is usually something that people are so uncomfortable with, because it’s not something that’s normal in our workplaces.” Naomi Hattaway
“Healthy systems don’t stop people from leaving, they make it possible for people to leave well.” - Naomi Hattaway
“Take one function of your role today... pick one function of your work and start to just line out what someone else would need to know if they were given that role to do the next day.” - Naomi’s One Good Thing
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