What We Made Possible

016. Leaving Well: Why Leadership Transitions Matter in Mission-Driven Organizations

• Patricia Dayleg • Season 1 • Episode 16

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On this solo episode of What We Made Possible, I dig deep into an often-overlooked but essential topic: what it really means to leave well in an organization.

Leaving—whether you’re a founder, executive director, or team lead—doesn’t have to be fraught with chaos, confusion, or burnout. I share one of the rare instances from my own career where a leadership transition actually felt healthy and whole, and unpack why it’s so difficult for most organizations to create that sense of trust, clarity, and continuity. If you’ve ever been in a nonprofit or mission-driven space, you know too well how destabilizing it can feel when transition planning is neglected. But it doesn’t have to be this way.

I walk through the ripple effects of “leaving well” (and not-so-well), from the emotional exhaustion of staff to the collective grief and readiness that can actually empower a team when done thoughtfully. Plus, I offer you concrete approaches, from leader coaching to team retreats and integration circles, so you can begin realigning for sustainability, whether you’re preparing to leave or picking up the pieces after a rocky departure.

If you’re craving more stability, transparency, and care in your organization’s transitions, this episode is for you. You’re not alone. Healthy goodbyes are possible, and together we can build cultures that sustain us, not just our missions. If you want to dig deeper or need support, my door (and calendar) are always open.