The Dropped Baton: Why Timing Is Everything in Succession Planning

When succession planning starts too late or moves too fast, leaders drop the baton—losing both momentum and legacy.

“The best time to plant a tree is twenty years ago; the second-best time is today.”

Since 2005, baton exchange failures have caused the U.S. men’s relay team to be disqualified or fail to finish six times, resulting in the worst rate of any national team.

These athletes are at the top of their game. But when the timing is off in that brief window of the relay box, they forfeit the win.

Many businesses fail in their leadership transitions for the exact same reason—timing.

This brings us to Pitfall #6: Failure to allow margin for new and unexpected opportunities by early planning.

I devote a whole chapter to this pitfall in my new book, Succession Planning for Impact (The Workbook).

If you wait too long to prepare the next runner or rush the exchange without room to adjust, you drop the baton. Successfully handing off leadership means creating margin—the time and space to plan early, train successors, and respond to the unexpected.

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>>> Your succession plan shouldn’t be a straitjacket. It should be a springboard for growth. <<<

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John’s Story: The Power of Margin

A few months after joining our Breakthrough group, our client John encountered an unexpected acquisition opportunity that perfectly complemented his core business.

Because he had started planning early enough to allow for margin, he was able to pause succession activities for three months to integrate the new company.

The result? His company doubled in value before transitioning, and he created three new leadership positions that strengthened his succession team.

“Without margin,” John later told the group, “I would have either missed that opportunity or derailed my entire succession plan trying to seize it.”

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What Early Planning Provides

Starting early isn’t just about preparing for an eventual handoff—it’s about creating space for magic to happen.

Room for Course Corrections: Like a ship on a long journey, winds change. Early planning provides time to adjust strategies, test new approaches, and learn from mistakes without catastrophic consequences.

Leadership Development Flexibility: Develop multiple succession candidates, rotate potential leaders through different roles, and let emerging leaders prove themselves.

Market Adaptability: Pivot without panic and align leadership development with evolving business needs.

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How to Build Margin Into Your Plan

Start earlier than you think you need to. Begin succession discussions while they still feel “premature.” Create space for natural leadership emergence.

Build in regular review points. Schedule quarterly plan reviews and adjust timelines based on actual progress.

Develop multiple leaders. Create a deep bench of potential successors so you’re never dependent on a single point of failure.

Create practice opportunities. Schedule intentional absences so next-generation leaders can practice running the company without you.

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Gil’s Story: The Victory Lap

Gil is the poster child for succession planning—proof that this method works.

He built margin into his transition by creating a seven-year plan for passing the baton. Currently, he works four days a week. Next year, he’ll reduce to three. By age 72, he will have passed all leadership to his three chiefs. His entire C-suite owns stock in the company—no small feat.

Gil is accomplishing what so few entrepreneurs do: living a life of significance. He’s making a difference today while ensuring his values live on long after he’s gone.

I want your story to be like Gil’s.

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The Magic of Margin

When you leave margin in your succession plan, something remarkable happens. Opportunities you never imagined emerge. New leaders step up in unexpected ways. The business becomes more adaptable, more resilient, and ultimately more successful.

Margin makes that possible.

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Ready to Create Margin in Your Plan?

The Succession Planning for Impact (The Workbook) gives you the tools to ensure you don’t drop the baton:

✅ Discussion Questions to identify where you lack margin

✅ The Pitfall #6 Checklist to audit your leadership bench and timeline flexibility

✅ Step-by-step guidance on building a multi-year transition

Don’t let poor timing cost you your legacy.

👉 Get the Succession Planning for Impact (The Workbook)

If an unexpected opportunity arrived tomorrow, would your succession plan allow you to seize it?