Coming to Terms with Age and Eventual Retirement: Succession Planning Should Start on Day One.
Christina M.E. Dodd
16 Jun, 2025
There’s a quiet moment that catches many leaders off guard. It’s not a loud boardroom epiphany or a dramatic life event. It’s the flicker of a thought, often late at night or early in the morning, when you realize: I won’t be here forever. For many, especially those in senior leadership, it’s not just about aging — it’s about legacy.
And yet, in all our strategic foresight, in all our quarterly goals, profit forecasts, and organizational change initiatives, we often avoid the most obvious and unavoidable transition of all: our own departure.
Succession planning is not a retirement activity. It’s not something to do when your knees start aching or your contract is coming up for renewal. Succession planning is leadership. It’s the most mature, strategic, and selfless form of leadership there is. And it should start on Day One.
Let’s talk about why.
Denial, Delay, and the Dreaded Conversation.
Let’s be honest. Many of us avoid succession planning because it feels too close to mortality. If we talk about “who comes next,” does that mean we’re replaceable? Are we admitting we’re slowing down? Are we letting go of power before we’re ready?
There’s a cultural discomfort around aging — especially in high-stakes leadership roles. We work in a world that values the relentless energy of innovation, the glittering seduction of disruption, and the optics of vitality. In that context, even mentioning retirement (“not the R word”) can feel like an admission of weakness.
But leadership isn't about clinging to relevance. It’s about creating it in others.
Succession planning — when done early, openly, and courageously — is one of the most future-facing acts a leader can perform. It's not about endings. It’s about seeding the future.
The Myth of the Perfect Moment.
“I’ll start thinking about that next year.”
“Let’s wait until after the product launch.”
“I’m too busy right now.”
Sound familiar? All too familiar. These are the internal scripts we use to delay the uncomfortable. But let’s call it out for what it is: procrastination in a leadership suit.
There is no “perfect time” to begin succession planning. Life doesn’t wait. Emergencies happen. People get sick. Boards change. Economic conditions shift.
A Harvard Business Review study once noted that the average CEO (of a major organization) gives less than two years' notice before stepping down — and often leaves behind a vacuum. Two years is a blink in leadership development. If you want someone truly ready to take your seat, you need to plant those seeds years earlier.
Succession planning isn’t an event. It’s a process. And it works best when it's woven into the culture of leadership from the start.
Start With This: Who Could Do My Job?
That’s a confronting and raw question. But it’s also a clarifying one.
Think about it. Who in your team, your organization, or even your wider industry could genuinely step into your role within the next three to five years?
Not perfectly. Not identically. But well enough to move the mission forward?
If the answer is “no one,” you’re looking at a leadership failure. Not because you haven’t performed. But because you haven’t prepared.
Succession planning starts with observation. Who’s curious beyond their role? Who has natural influence? Who steps up in crises, without needing to be asked? Who listens well? Who learns fast? Who carries a sense of ownership?
Identify these people early. Then build with them, not just for them.
The Leader as Gardener, Not Gatekeeper.
There’s a fundamental shift required in the way we see ourselves.
Too often, leaders unconsciously adopt a gatekeeper mentality — guarding knowledge, relationships, or influence as a means of maintaining authority. That’s human. But it’s also short-sighted.
What if, instead, we saw ourselves as gardeners?
Gardeners prepare the soil. They plant with care. They nurture quietly, over time. They create conditions that allow others to grow — even after the gardener has moved on.
Leadership isn’t just about what you can achieve. It’s about what can continue without you. When your departure — whether temporary or permanent — is met with strength, clarity, and continuity, that’s real success.
This mindset shift also lightens the psychological load of leadership. You stop seeing your role as a fortress to defend and begin seeing it as a platform to elevate others. That changes everything.
Building Bench Strength: It’s Not Just One Name.
One of the common mistakes in succession planning is focusing on one person: the “heir apparent.”
While it’s tempting to anoint a single successor, this approach is risky. People leave. Life intervenes. And no one individual should carry the entire weight of continuity.
Instead, think in terms of bench strength. Who are the top five people who could take on different aspects of your role? Who’s being groomed for senior roles across functions? Who could lead with others, not just after you?
Think of it like this: you’re building a constellation, not a clone.
This also helps mitigate internal politics. When succession is seen as a shared, structured, and strategic initiative — rather than a secretive game of favorites — it builds trust rather than competition.
The Hardest Part: Letting Go.
Eventually, the day will come when you’ll leave. We all must face it.
It’s a reality we can’t ignore or wish away.
Maybe it’s voluntary — a new chapter, a well-earned retirement, a board seat, or a passion project.
Maybe it’s unexpected — health, family, politics, or economic downturns. Either way, your chair will be filled by someone else.
If you’ve planned well, that moment won’t feel like erasure. It will feel like release.
But to get there, you’ll need to confront your ego.
Many leaders fear being forgotten. That’s natural. But legacies aren’t built on tenure. They’re built on impact. If people continue to thrive, grow, and evolve because of what you seeded — that’s the kind of leadership that echoes long after your name is off the door.
Letting go doesn’t mean disappearing. It means transitioning with grace. It means offering mentorship, not meddling. It means trusting the future you helped create.
Case Study: Succession Gone Right.
Let’s look at a real-world story of succession done well.
Naomi, the CEO of a mid-sized healthcare company, started thinking about her exit a full five years before she planned to step down. She didn’t announce anything. She simply started observing more intentionally — identifying who on her executive team had growth potential.
She initiated one-on-one development conversations with three people, giving each the opportunity to shadow her on certain projects, lead executive meetings in her absence, and build cross-functional relationships across the business.
Crucially, she didn’t turn it into a race. She framed it as leadership evolution, not competition. And when one of the candidates eventually left for a competitor, she didn’t panic — because she’d built multiple pathways forward.
Three years before her planned exit, she began informal conversations with her board. Two years out, she announced her retirement internally and supported a formal recruitment process that included internal and external candidates.
Her successor — one of the three original leaders she’d mentored — took the reins with full stakeholder confidence, having already led several company-wide initiatives and having built deep trust with the team.
Naomi transitioned to a strategic advisory role, where she continued to contribute without overshadowing. The company didn’t just survive the transition — it thrived.
This wasn’t luck. This was foresight.
Practical Steps to Begin Now.
Whether you’re 30 or 60, whether you’re a first-time leader or nearing the end of your long executive career, here are seven steps you can begin today:
Shift your mindset: View leadership as stewardship, not ownership. You’re a builder of futures, not a holder of seats.
Spot potential early: Look for values alignment, curiosity, resilience, and emotional intelligence — not just performance metrics.
Have honest conversations: Begin leadership development dialogues without fear. Name the growth you see in others. Invite their aspirations.
Document your knowledge: Don’t keep your wisdom in your head. Build knowledge systems, playbooks, and cultural handovers.
Create stretch opportunities: Let emerging leaders step into the spotlight — present to the board, lead strategic initiatives, handle crisis situations with your guidance.
Involve the board or governing body: Keep them informed of your long-term view. Help them see succession planning as a priority, not a panic.
Know your finish line: Have clarity on what “done” looks like for you — whether that’s a specific date, milestone, or set of conditions.
Succession as Emotional Leadership.
Succession planning isn’t just structural. It’s emotional. It’s about trust. Vulnerability. Humility. Letting go of the illusion of irreplaceability. Nurturing the next generation even when you’re still in the game.
And that, perhaps, is the most emotionally intelligent act a leader can offer.
We often talk about succession as a risk — but it’s also a gift. It gives others permission to rise. It creates safety in uncertainty. It sends a message to the organization that leadership is an evolving journey, not a static position.
In Closing: What Will You Leave Behind?
When the day comes that you step away — not just for a holiday or a sabbatical, but for good — what will remain?
Your vision? Your culture? Your values? Your people’s capacity to lead without you?
Or will there be a scramble, a vacuum, a search for clues?
Succession isn’t the end of leadership. It’s the highest expression of it.
Start now. Start today. Not because you’re old. Or getting older. And not because you’re tired. But because you’re wise enough to know that the true measure of leadership is not what you do during your time — but what endures after it.