A Tale of Two Leaders: Succession Planning That Secures the Future
Succession isn’t about retirement.
It’s about responsibility.
This post tells the story of two very different outcomes — one anchored in foresight, the other in delay. And in those differences lies a blueprint for any family business leader who wants to exit well, not just exit eventually.
Case One: George Steinbrenner: Building a Bench Before You Need One
George Steinbrenner wasn’t just the owner of the Yankees. He was the Yankees. Fierce, outspoken, impossible to ignore.
But behind the bravado was something quieter: foresight.
He didn’t wait for a crisis. He began succession years before he stepped back inviting his children into decision-making roles, mentoring them, and letting them fail safely.
By the time he exited, the transition was seamless. The organisation didn’t collapse; it carried forward, rooted in both legacy and competence.
Case Two: Richard Murdock: Waiting Too Long to Ask “What If?”
Richard Murdock built a powerhouse of media and publishing.
But while the front page changed daily, his own plans didn’t.
Succession? It could wait.
Then came illness. And with no plan in place, his empire began to fray. The absence of clear leadership bred division. Family members jostled. External forces circled. What should have been a proud handover became a cautionary tale.
The Lesson for Family Businesses
Too often, family leaders hope to control the ending.
But here’s the truth: if you haven’t planned your exit, you’re already losing control.
Succession is not a moment. It’s a strategy.
Handled well, it becomes your final act of leadership. Handled poorly, it becomes the beginning of decline.
Frequently Asked Questions
Q: When is the right time to start succession planning?
Earlier than you think. Ideally, five to ten years before you step back, even if you don’t know the exact date yet.
Q: What if I don’t have an obvious heir?
That’s more common than you think. Succession is about readiness, not birthright. You may need to develop leaders from within or consider trusted external candidates who align with your values.
Q: How do I involve family without creating resentment?
Start with honest conversations. Make expectations clear. Give family members the chance to earn their place rather than assume it.
Q: What if I still want to be involved?
You can be, but in a new role. Think coach, not captain. Influence, not interference.
Q: Isn’t succession just legal paperwork?
No. That’s the final step. The real work is emotional, strategic, and cultural. It’s preparing people, not just processes.
Lead now for what comes next.
Start your succession conversations before they’re urgent.
Mentor your replacement while you’re still present.
Put structures in place that survive you — because the best leaders don’t just build; they prepare others to carry on.
🔹 Map out a transition timeline.
🔹 Talk to your family — and your team.
🔹 If you’re unsure how to begin, bring in someone who’s done it before.
Because succession isn’t just about the future.
It’s how you lead today.
And one day soon, that moment will arrive.
Will your business be ready?
Will they?
Will you?
Let’s make sure the answer is yes.
Stephen Bray helps founders untangle what’s really going on beneath the surface. They then make better choices from there. Meet the man behind the mirror here.
© 2025 Stephen Bray. Patterns in life and business, simply told.