Episode Overview
Theme:
“People Leave: Make Transition Readiness Part of Your Culture”
In this thought-provoking episode of the We Are For Good Podcast (Episode 673), hosts Jon McCoy and Becky Endicott are joined by nonprofit leader and transition strategist Naomi Hattaway. Together, they tackle the rarely discussed—yet inevitable—reality of staff transition in nonprofits. The conversation dives deep into why embracing and preparing for staff departures must become integral to organizational culture and health, especially amidst sector-wide uncertainty.
Key Discussion Points & Insights
1. Normalizing Turnover (00:00–03:50)
- Naomi Hattaway opens by addressing the elephant in the room: people leave, and organizations must face this truth head-on, not as an emergency but as an ongoing reality.
- “There are people on your team, as you're listening to this, that are planning to leave, and you're listening to this, and you might be planning to leave also.” — Naomi [00:00]
- Jon echoes a recent LinkedIn post, reinforcing that departure is especially prevalent at the start of a new year—when reflection leads to change.
2. Building Organizational Health Amidst Uncertainty (03:50–07:05)
- Naomi draws a parallel between dental and organizational health:
- “If we don't tend to the reality that people leave, what does the rest of it even matter?” — Naomi [03:51]
- The social impact sector is experiencing scrutiny and instability—funding cuts, leadership churn, and pressure around equity—making transition readiness more essential than ever.
3. Practical Tools for Transition Readiness (07:05–12:32)
- Reserve Policies:
- Health includes organizational reserves for navigating departures and succession planning—not just financial emergencies.
- “Uncertainty to me always looks like change happens to us. Transition is what we can do about it.” — Naomi [05:26]
- Four Core Practices:
- Honest infrastructure (documentation)
- Endings literacy
- Financial truth-telling
- Distributed knowledge
- Documentation is Key:
- Start with relationship maps, brain dumps, and memos of transition work.
- “How would you ever want to leave your legacy or the mission of your organization without documenting what's in your head?” — Naomi [08:14]
- Scrappy, informal documentation (“scribbles on a napkin over nothing”) is often more useful than polished, unused playbooks.
4. Developing Endings Literacy: Embracing and Learning from Departures (12:32–16:07)
- Culturally, discomfort with endings means poor handling of staff departures, leading to avoidable disruption.
- “Ending's literacy starts when you can name the thing.” — Naomi [12:52]
- Start with non-threatening discussions, like board term completions, to open up conversations about endings.
- Recognize that individuals' reactions to endings are deeply personal and influenced by individual histories.
5. Financial Truth-Telling & Planning for Transition Costs (16:07–19:23)
- Acknowledges the real costs—both hard (search, agency fees, stipends) and soft (lost capacity, morale)—of staff transitions.
- Encourages organizations to plan for these costs up-front, including interim roles and stipends for internal candidates.
6. Distributed Responsibility for Transition Readiness (19:23–20:21)
- Everyone, regardless of role, can contribute—through small acts like documentation or by initiating culture shifts in team meetings.
- Leaving a legacy doesn’t require formal authority: “You can leave crumbs, you can leave back-on-napkin stuff, you can leave a Loom video for your team.” — Naomi [19:23]
7. Tending to the Emotional Side: Grief, Loss, and Honoring What Came Before (20:21–25:39)
- Naomi shares her interim leadership experience—where often she arrives after a sudden departure or even a death.
- Key rhythms introduced:
- Space for grief and the naming of loss
- “Katie's Way”: Retaining and celebrating positive elements from departing leaders
- Regular team “temp checks” to provide support tailored to different coping styles
8. Succession Planning: Beyond the Check-the-Box Approach (25:39–27:33)
-
Succession planning must not remain a closed-door activity or a static document; it needs to be “taken off the shelf” and woven into day-to-day culture and conversations.
-
Organizations where succession is lived (not just planned) foster more trust and resilience.
- “Healthy systems don't stop people from leaving. They make it possible for people to leave well.” — Jon quoting Naomi [27:54]
9. Leaving Well: Individual, Organizational, and Community Impact (27:54–31:01)
- For individuals: Honest exit conversations, transparency about reasons for leaving, and authentic expression.
- For organizations: Budgeting for transition, enabling offboarding conversations, and communicating with those served—removing shame from the process.
10. Human-Centered Change Under Stress (31:01–33:37)
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Naomi emphasizes dignity in departures, transparency, and small but meaningful gestures (like a DoorDash card during layoffs) as examples of care.
-
She encourages extending support—EAP benefits, therapy, practical resources—to those going through transition.
- “Truth tell with compassion. It beats false reassurance every time.” — Naomi [31:01]
11. Practical Homework & Closing Wisdom (34:13–39:27)
- Naomi’s “one good thing”:
- Pick one key task in your current role and document it, as if someone needed to do it tomorrow.
- Share this with a teammate to spread the culture of readiness.
- “Your someday of someone leaving is today.” — Naomi [34:45]
- She urges organizations to include “strategic sunset scenario planning” on board agendas to reduce harm to staff and communities if closure becomes necessary.
- Colleen Hacker (sports psychologist) is quoted: “Do good now.”
Notable Quotes
-
“There are people on your team, as you're listening to this, that are planning to leave, and you're listening to this, and you might be planning to leave also.”
— Naomi Hattaway [00:00] -
“If we don't tend to the reality that people leave, what does the rest of it even matter?”
— Naomi Hattaway [03:51] -
“Uncertainty to me always looks like change happens to us. Transition is what we can do about it.”
— Naomi Hattaway [05:26] -
“Ending's literacy starts when you can name the thing.”
— Naomi Hattaway [12:52] -
“Healthy systems don't stop people from leaving. They make it possible for people to leave well.”
— Jon quoting Naomi [27:54] -
“Your someday of someone leaving is today.”
— Naomi Hattaway [34:45] -
“Do good now.”
— Colleen Hacker, via Naomi Hattaway [36:51]
Timestamps for Important Segments
| Timestamp | Segment Description | |-----------|---------------------------------------------| | 00:00 | Opening truth: People leave | | 03:51 | Dental health analogy & tending to turnover| | 07:30 | Four must-haves for healthy transitions | | 08:14 | Practical documentation advice | | 12:32 | Endings literacy and talking about loss | | 16:20 | Accounting for the real cost of departures | | 19:23 | Distributed responsibility & personal legacy| | 20:51 | Grief & honoring departures as interim | | 27:54 | "Leaving well" defined, mic drop moment | | 31:01 | Human-centered transition under stress | | 34:45 | "One good thing" homework assignment | | 36:51 | “Do good now.” - closing wisdom |
Memorable Moments
- “Katie’s Way” — Memorializing the best of a departed leader while preparing the team for what’s next. [20:51]
- USB drawer story — Naomi finds an office with mysterious drives and keys, underscoring why documentation matters. [24:19]
- Practical takeaway: Document one function of your job today as if someone else needs it tomorrow. [34:45]
Tone & Language
- The conversation is direct, candid, and deeply human, balancing practical advice with empathy and realism. Naomi and Jon model vulnerability, humor (“go to the dentist!”), and hope, making difficult topics accessible and actionable for mission-driven listeners.
Resources & Connect
- Naomi Hattaway: naomihattaway.com
- Transition archetype quiz for teams
- Board development, transition coaching, interim leadership
- LinkedIn: Naomi Hattaway
- Instagram: @naomihattaway
This episode is essential listening for nonprofit leaders and teams ready to stop fearing turnover—and start building cultures where every transition strengthens the mission and the people behind it.