Today we’d like to introduce you to Naomi Hattaway.
Hi Naomi , thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
I built my practice around one unavoidable truth: People Leave™️. Every organization will face leadership transitions—through retirement, family leave, resignations, or unexpected departures. Yet most nonprofits operate as if their current leader will be there forever.
My start came from my own departure from an international affordable housing nonprofit. I had been appointed the Deputy Director, as part of a succession planning initiative from the board of directors, yet the Executive Director didn’t have any intention of going through the process to knowledge share, share leadership, etc. During my departure (I decided to leave after realizing there were some large values misalignments), I started realizing there was a systemic issue in organizations around succession planning and being prepared for workplace transitions.
I provide interim executive leadership and proactive succession planning because I’ve seen too many mission-critical organizations nearly collapse when leadership gaps hit. My work spans nonprofits, family businesses, the sports world (so many departures and transitions!), and entrepreneurial ventures—all facing the same reality that leaders eventually move on, and most are catastrophically unprepared.
The “Leaving Well” framework I’ve developed helps organizations embed transition planning into their culture, not treat it as crisis management.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
The biggest challenge has been convincing boards, business owners, and leaders to plan for something they don’t want to think about. Succession planning feels like writing your estate plan, or planning your own funeral—uncomfortable and seemingly premature.
I’ve watched organizations hemorrhage talent, lose major grants, and damage community relationships because they waited until leadership crises hit to start thinking about transitions. In the sporting world, transitions (front office, coaching staff, support staff, players and athletes themselves) impact performance in the field (and ultimately wins!).
The resistance isn’t malicious; it’s human nature. But it’s also expensive and preventable.
Building credibility in this space meant being willing to have uncomfortable conversations and challenge the tendency to operate in reactive mode rather than strategic foresight.
Alright, so let’s switch gears a bit and talk business. What should we know?
I specialize in interim leadership and succession planning with a fierce focus on accountability as a gateway to courageous conversations. This isn’t feel-good consulting or advisory services—it’s practical preparation for inevitable reality.
What sets me apart: I tell boards that current board members should never serve as interim EDs. I push organizations to distinguish between kindness and niceness in leadership transitions. I help teams activate their “quiet power” rather than waiting to be “empowered” by others. I bring out the reality that People Leave in a way to support proactive work towards sustainability and help folks become more resilient to change and transition.
I’m known for creating healthy workplace transition cultures where leaving well becomes the norm, not the exception. Whether it’s a $50M foundation, a team (of any type) or a grassroots nonprofit, the principles remain: prepare early, communicate clearly, and honor both the departing leader and the organization’s future.
Who else deserves credit in your story?
Every client who trusted me with their leadership transitions deserves credit—especially the brave decision makers who have engaged me for succession planning while they were thriving, not just when crisis hit.
The board chairs who acknowledged they needed outside perspective during vulnerable moments.
The interim leaders who came before me and proved that external leadership during transitions works.
The team members of the clients I’ve worked with along the way who’ve proven to me that healthy transition cultures aren’t just nice-to-have—they’re essential for mission sustainability.
The foundation program officers, donors, CEOs, GMs, and philanthropists who fund succession planning initiatives also deserve recognition. They understand that leadership development and transition planning are infrastructure investments, not luxury add-ons.
They’ve all taught me, and underscored, that when people leave well, organizations can emerge stronger than before.
Contact Info:
- Website: https://naomihattaway.com
- Instagram: https://instagram.com/naomihattaway
- LinkedIn: https://linkedin.com/in/naomihattaway
- Youtube: https://www.youtube.com/@LeavingWell
Image Credits
Daniel Muller
Rebecca Gratz
