Let's talk about the question your board isn't asking out loud: Is it time for our ED/CEO to leave? Not because they're failing. Not because they're old. But because the organization likely needs something different than what they can deliver right now, or needs to prepare for when that time comes. New McKinsey research on 200 top CEOs found that leaders in their final stage—"Winter"—have predictable blind spots. The most critical one: recognizing when to leave is a leadership competency, and...
11 days ago • 1 min read
After four seasons and nearly 100 episodes, I'm closing the Leaving Well Podcast. Not because the work is done—far from it. But seasons end, and practicing what I preach means leaving while there's still intention and love for the work. The final Season 4 episodes will release over the coming months. But first, I want to share what this journey taught me—and what it means for your organization's next transition. What 100 Leaders Taught Me When I launched in September 2023, I knew nonprofits...
22 days ago • 3 min read
This podcast conversation with Kate Harris landed differently than most. Kate runs KHG Nonprofit Strategy and has spent years doing work that most of us avoid: mergers, dissolutions, and what she calls "structural change." Not because organizations are failing, but because structure is the vehicle—not the destination. Here's what stuck with me: Your mission is your destination. Structure is just the vehicle getting you there. Most nonprofits pick a vehicle and never reassess whether it still...
24 days ago • 1 min read
*We are continuing our experiment with a longer form email structure. Less quick + easy, more deep + thoughtful." Would love to hear your thoughts! You're reading this because you know the power of transitions. Maybe you're an ED planning your exit, a board member preparing for leadership change, or a funder watching organizations navigate the uncertainty of what comes next. Today's conversation is about something we rarely discuss: how to give everything to work you know will end. My guest,...
about 2 months ago • 4 min read
*We are experimenting with a longer form email structure. Less quick + easy, more deep + thoughtful." Would love to hear your thoughts! I just finished a podcast conversation about sabbaticals with Alexander Lapa, and he said something that stuck: "I always had the perception of sabbatical as being a one-time thing, but I just realized there's no actual limit to it." That moment of recognition? It's exactly what needs to happen in boardrooms across the nonprofit sector. Let's Address the...
2 months ago • 4 min read
The biggest business challenge in launching my Leaving Well work has been convincing boards, nonprofit leaders (and funders) 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. The...
2 months ago • 1 min read
Target's CEO succession is giving every nonprofit board some homework they probably don't want to do. Brian Cornell stepped down last week after 11 years, and the board promoted COO Michael Fiddelke to CEO. Clean, planned, internal promotion. Textbook succession planning, right? Except for one uncomfortable detail: Target has been losing ground to competitors for years under the leadership team Fiddelke was part of. Here's the question Target's board just forced into the open: Should the...
2 months ago • 2 min read
The Dallas Cowboys Cheerleaders are a spectacle of precision—every hair curled, every toe pointed, every smile practiced. But behind the sequins and stadium lights is a relentless cycle of selection and cuts. Watching the Netflix series about their process, I found myself realizing the similarities between what they’re navigating—high turnover, legacy leadership, untold grief, and zero succession infrastructure—isn’t just reality TV. It’s what I work with every day inside nonprofits and...
3 months ago • 1 min read
For many folks, it feels scary to begin thinking about leaving their organization, and even scarier still to think about how to begin TALKING about it. I'm excited to share a few examples of Leaving Well, in the wild. Real world opportunities to learn from others who are treating their departures as something they are able to navigate, on their terms, as well as a few "as soon on" podcasts to share. First up, Dr. Sherece Y. West-Scantlebury, who is retiring from the Winthrop Rockefeller...
3 months ago • 1 min read