A fellow board member asked me a question recently that I couldn’t answer: “If our CEO got hit by a bus tomorrow, who runs this company?”
My silence said everything. Because, as a board member or advisor of numerous companies over the last decades, I have experienced this terrible occurrence four times. So, I know the feeling of shock and vulnerability.
Here’s what most leaders won’t admit:
We avoid succession planning because it forces us to confront our own mortality and replaceability. It feels like planning your own obsolescence.
But here’s the truth I learned the hard way: if you haven’t trained your successor, you haven’t finished your job.
[Email readers, continue here…] I’ve seen other companies face sudden CEO departures or worse. The contrast in outcomes was stark.
In one, the board stepped in immediately. They had a succession plan. They elected a new CEO from within the board, reached out to stakeholders with a clear transition plan, and the business continued with minimal disruption.
In another, the board was completely unprepared. No plan. No obvious successor. No documentation on critical relationships or ongoing negotiations. Chaos.
In a third, a sales manager was elevated to CEO without experience, and that company slowly declined over time.
In the fourth, I stepped in as chairman and became CEO effecting an organized transition the employees appreciated, avoiding the chaos and uncertainty.
The difference wasn’t luck. It was preparation.
Most leaders treat succession planning like estate planning. Something they know they should do but keep postponing because it’s uncomfortable.
But succession planning isn’t about you stepping down tomorrow. It’s about building an organization that can thrive without you being the critical dependency for every decision.
Here’s what real succession planning looks like: you’re actively developing someone who could step into your role. Not someday. Now, if needed.
You’re sharing context, not just tasks. They understand why decisions are made, not just what gets decided. They’re sitting in on critical meetings. They build relationships with your key partners, investors, and customers. They know where the bodies are buried and where the opportunities hide.
You’re also documenting the undocumented. The vendor relationships that depend on a handshake. The customer quirks that aren’t in your CRM system. The board dynamics that determine which battles are worth fighting.
But here’s what stops most leaders:
Ego. The belief that you’re irreplaceable. That the company needs you specifically, not just someone in your role doing it well.
That’s not confidence. That’s insecurity dressed up as indispensability.
The strongest leaders I know measure their success by how ready their organization is to succeed without them.
