A natural part of the exit planning conversation is also succession planning. The two go hand in hand.
If you’ve ever dreamed of replacing yourself in the business, here are a few hard-earned insights I’ve developed over the years as I’ve helped leaders make this transition:
Succession isn't about replication. It's about elevation.
Tenure doesn’t equal readiness. The longest-serving /surviving exec might not be your best successor. Loyalty important, sure - but capability wins.
Different doesn’t mean deficient. Your successor’s style may differ from yours. It most likely will, hence why you two worked so well in the past. This is not a bad thing and most certainly isn’t a threat. Rather an opportunity to infuse a different energy into the business. Maybe one that’s well needed.
Respect is critical. Without it, their effectiveness will be capped.
They are mortal. Plan for their successor too. That’s real stewardship.
Comp needs to match context. Different values, stages, and incentives may apply. Align on future outcomes, not past structures and formulas.
Ownership mindset is non-negotiable. If they’re waiting for the ball, they’re not the one. You want a quarterback, not a receiver.
Think systems, not silos. They must see the whole board - not just their piece. Cross-functional fluency is also non-negotiable. At this level it’s about the big picture.
Better than you is the bar. But if they’re 90% as good and the org still thrives - that’s a win.
Co-creation is required. This isn’t a handoff. It’s a build-with process: enrollment, iteration, authorship.
It might not work. That’s reality. Have a plan for that too.
It might work. And if it does, you’ve just bought yourself freedom, legacy, and peace of mind.
Succession done well beats the alternative.
Poll Results: The results are in from last week’s survey:
51% of voters said they prefer to “Fail Fast”
Song of the week…
Tim Martinez
“The Inside Man”
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Fantastic insights. The thought of replacing yourself or finding a successor is one of those things everyone needs but doesn't think about. Your thoughts on this are eloquent and thought provoking indeed. As important as getting your affairs in order.. A must for a thriving company, family and/or society.