Diane Tavenner spent eight months working side by side with the person who would replace her.
She co-founded Summit Public Schools with a single high school and grew it into a network across California and Washington. When it came time to hand it off, she worked with her successor to build a plan together: on-ramping the new CEO, off-ramping herself, co-leading some things and gradually letting go of others.
Then she did something most founders avoid. Before leaving, she committed to a handful of what she called "really hard, yucky things" - the moves that had to be made to make space for her successor to lead, ensuring she wouldn't face those roadblocks on day one.
When she joined me on Hire Ground Podcast, she put it simply. As a leader leaving, maybe your greatest responsibility is to create the conditions for success for the new CEO - a perspective that may seem obvious but is less common among founders than you would think.
Most conversations about founder transitions focus on the founder who won't let go. That founder is real. But Diane named a second problem I see just as often: the founder who waited too long to transition so by the time the moment comes, they are just ready to be done. Their attention is on the exit for themselves - not what the org and their successor need to be effective going forward. As a result, the hard decisions get deferred, the relationships don't get transferred, and the new leader walks into a backlog with a whole set of challenges they didn't create but they do now own.
Doing it Diane's way can, in the short term, be a harder road for the founder. It means making the unpopular call on the program that no longer fits, the structure that doesn't scale, or the senior leader who isn't working out, and leaving as the person who made it. It means accepting that the next leader may run things differently, and that different might be better. A founder whose main priority is to be remembered fondly by everyone could find that hard. But, a founder who wants the organization to thrive without them will do it anyway.
Diane also pushed her board in a direction many boards resist. Instead of launching a national search for an imagined unicorn, Summit's board defined the bar the next leader had to clear, recognized that more than one person could clear it, and chose from there. That spared the organization the months of angst and hard feelings that a big, open-ended search can produce, especially when strong internal candidates are watching.
Which brings me to boards. Most founders are not as brave and committed as Diane. They won't volunteer to do the yucky things. They need a nudge, and the board is often the only body positioned to give it. That usually means the chair, in a direct conversation well before the search launches: "What are the hardest decisions this organization is facing? Which of them will you make before you go?"
It also means the board holding a line on the founder's role afterward. Diane's eight months of overlap worked because they had a plan and an end. Overlap without an end date stops being a handoff and becomes a second center of gravity.
None of this is about diminishing founders. The founders I admire most treat the transition as their last act of leadership, and the hardest one, because the measure of success is someone else's.
If you're a founder thinking about what's next, start with a short list: the decisions your successor shouldn't have to make. Then make them.
To listen to the full Hire Ground Podcast episode with Diane Tavenner, click here. And download the Edgility Search succession planning toolkit through this link.
Christina Greenberg is CEO of Edgility Search. Follow her on LinkedIn to join the conversation.