When it's time for your ED or CEO to go (and why they can't see it themselves)


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 most leaders don't have it.

Winter isn't age-based. It's accountability-based. It arrives when:

  • Strategic clarity fades (playing it safe or making erratic moves)
  • The succession process goes under-managed
  • The leader's self-assessment doesn't match what the board and team see (which happens 100% of the time, according to the data)

Here's what this means for boards: Waiting for your ED/CEO to recognize it's time is a failure of governance.

The best transitions happen when boards step in proactively—not because the ED is unsuccessful, but because recognizing the right moment to leave is nearly impossible to see from the inside.

Whether you're a board member or an executive leader, your job isn't to wait for a crisis. It's to see Winter coming and plan accordingly.

I help boards navigate this exact moment—when you know change is needed but the path forward isn't clear. If you as a leader, or as a board member are sensing it's time but do not know how to move forward, let's talk.

This isn't personal. It's critical.

P.S. The McKinsey research backs up what you're probably already sensing. Trust that instinct.

Gravel Road, Chattahoochee Hills, GA 30213
​Unsubscribe · Preferences

Leaving Well in the Workplace

Your Leaving Well guide to navigating workplace transitions 🧡 I normalize workplace transitions one organization + person at a time. Leaving Well is the art + practice of leaving in the workplace, with intention + joy.

Read more from Leaving Well in the Workplace

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...

A photo graphic of Kate Harris. The text says: Kate Harris on Structural Change as a Tool for Social Change

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...

*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,...