Naomi Hattaway: Navigating Workplace Transitions

Naomi Hattaway is the founder of Leaving Well, a practice devoted to helping organizations treat leadership transitions not as crises or cleanups—but as acts of cultural maturity. She works with mission-driven teams to address board development, succession planning gaps, and workplace transition support. Through interim executive leadership and advisory services, Naomi's work lives at the intersection of trust-building, systems change, and the radical belief that how we end things matters just as much as how we begin.

Key Takeaways:

• Leadership changes are often treated as crises even though they are normal and predictable. Naomi reframes exits as acts of cultural maturity rather than simple HR events. Thoughtful offboarding helps organizations create healthy closure and continuity.
• Transitions affect not only leaders but also the team that remains. Founder departures can trigger identity questions when organizations are built around one personality. Acknowledging grief and uncertainty helps teams move forward with clarity.
• Succession planning should involve the whole team, not just top leadership. Documentation, relationship handoffs, and knowledge transfer strengthen organizational resilience. Sabbaticals and temporary leaves can help organizations practice navigating absence and return.
• People respond to change in different ways, and each style brings value. Understanding these differences helps teams balance stability with forward movement. Healthy organizations accept that transition is messy but handle it with intention and care.

“We need to normalize the reality that people leave.”

“We put so much effort and beautiful intention into the onboarding, and then the offboarding is not the same level of energy.”

“We have to start somewhere by being a little bit better to each other when it comes to goodbye.”

- Naomi Hattaway

Reach out to Naomi Hattaway at:

Website: https://naomihattaway.com/

Instagram: https://instagram.com/naomihattaway

LinkedIn: https://linkedin.com/in/naomihattaway

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