The Conversations We Avoid: Succession, Retirement, and Age
At a recent talk in Dubai with business leaders from both family businesses and non-family-owned businesses, I had the opportunity to speak about a subject that many in leadership—whether in family enterprises, corporate environments, or entrepreneurial ventures—struggle to address: the conversations we avoid. These are the topics that shape careers, businesses, and legacies, yet they often remain largely undiscussed.
As part of my upcoming book, Unspeakable, I’ve been exploring the issues that leaders tiptoe around, despite their significance. One of those issues—succession, retirement, and age—was the focus of my conversation in Dubai. But regardless of whether a business is family-owned or not, these challenges remain universal.
Why Do We Avoid Talking About Succession?
One of the greatest challenges in leadership is knowing when to step away. Many founders, executives, and business owners hold on for too long, often without a clear transition plan in place. The reasons for this are deeply personal. Some see their work as their identity—if they step away, what’s next? Others feel an obligation to continue leading, worried that no one else will protect what they’ve built.
But avoiding the conversation doesn’t stop time. The reality is that longevity is changing career trajectories. If life expectancy continues to rise, we will see more CEOs in their 80s and 90s. Without structured succession planning, businesses will stall, corporate leaders will hold on past their prime, and talented next-generation leaders will move on rather than wait indefinitely for their turn.
We often look at public figures who have navigated succession—some well, some poorly. Warren Buffett has been widely celebrated for his clarity on wealth distribution but remains quiet about his succession plan. Queen Elizabeth, for all her wisdom, left King Charles in a position where he had to wait for decades without an endorsement. Planned transitions create stability. Emergency transitions create uncertainty.
Retirement as a New Chapter, Not an Ending
Another reason succession conversations get avoided is the false perception that stepping away equals fading into irrelevance. In reality, the best leaders embrace career transitions as a new chapter rather than a conclusion.
I shared the story of a leader who made a bold career move in his late 40s, leaving behind a prestigious position to pursue new ventures. Instead of staying in one role for life, he went on to advise some of the world’s largest companies, invest in major ventures, and even become an owner of a professional sports team. His story is a reminder that reinvention is possible at any stage.
Yet, in leadership roles across industries, we still see individuals who stay until they have nowhere else to go. Without a vision for what comes next, they cling to their roles rather than transition leadership. The healthiest organizations encourage leaders to think about what the next phase of their life could look like—whether that’s serving on boards, mentoring the next generation, or even pursuing personal passions.
Decoupling Age from Leadership
Age and succession have been so intertwined for so long that we’ve developed rigid expectations—retire at 65, move aside for younger leaders, or assume that older leaders should automatically step away. But the truth is, age shouldn’t dictate succession—ability and readiness should.
Some of the most effective leaders today are in their 70s and 80s. At the same time, younger leaders who are prepared should not have to wait indefinitely. Organizations need to move away from the idea that someone has to be a certain age to lead or a certain age to step down.
Finding Balance and Embracing Change
I left the group with a challenge: think of your life in chapters, not as one long, unchanging career. We often have clear phases in our youth—school, first job, early career moves—but somewhere along the way, people stop seeing new chapters as necessary.
The best leaders are lifelong learners who evolve over time. They embrace reinvention, create space for new voices, and prepare for what’s next before it’s too late.
So, the real question isn’t when you should transition leadership—it’s how you plan for the next phase in a way that allows both you and your organization to thrive.
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