Leadership transitions rarely happen on your timeline. That’s why preparing both yourself and your successors has to start now.
You can’t harvest what you never planted. Succession planning is no different. It’s not something you can scramble to do when the crops are already ripe; it has to start in the off-season. You plant seeds by developing talent, you tend the field through mentorship and training, and when it’s time to reap, others know how to bring in the harvest. Wait too long, and the season slips away — along with the future.
Leaders share two barriers to succession planning:
- “I’m not ready to take the next step.”
- “There’s no one ready to take my place.”
When “I’m Not Ready” Becomes the Excuse
This barrier often hides behind noble-sounding sentiments like, “My work here isn’t done,” or “I don’t want to abandon my team.” But under the surface, it’s usually about uncertainty — about the next role, about identity, about purpose after stepping away.
Leadership roles can become a source of personal meaning. And letting go of control—especially after years of success—can feel like losing a part of yourself. It’s natural to hesitate.
Waiting until you feel 100% is a false ambition. Leadership transitions are rarely about stepping away all at once. Leadership development is about evolving your contribution — shifting from execution to guidance, from doing to developing. You don’t have to walk away tomorrow. But you do have to start preparing for change — because you might be asked to walk away tomorrow.
No One’s Ready — Because You Haven’t Let Them Be
Succession is rarely about finding someone identical to you. It’s about building a team that has the capabilities, confidence, and context to take on greater responsibility. That doesn’t happen automatically. Often, leaders hesitate to delegate big responsibilities because they fear failure — or because they’re moving so fast that teaching slows things down.
Developing successors takes time, intention, and practice. It means giving people space to stretch, to make mistakes, and to grow under your guidance. It requires being proactive — not reactive. It’s not just about choosing a single successor. It’s about building a bench so that multiple people are moving toward readiness.
You Can’t Plant One Field and Ignore the Next
Succession planning isn’t a linear process. You can’t wait until you’re ready to move before you develop others. And you can’t hold back your own growth because no one else seems prepared. You have to do both at once — just like a good farmer makes decisions that consider both the current crop and next season’s crop.
Here’s what that looks like in practice:
- Define your legacy — Be clear about the impact you want to leave behind.
- Talk about your future — Have candid conversations with yourself and trusted advisors.
- Name your bench — Identify at least three potential successors and learn what they aspire to.
- Delegate real responsibility — Hand off four meaningful projects, not just tasks.
- Coach in the moment — Give feedback and stretch assignments consistently, not occasionally.
- Set a transition timeline — Even a rough roadmap keeps momentum alive.
- Ask the hard questions — What do I need to grow into? Who do I need to grow with me?
If You Hoard the Harvest, You Starve the Future
Leadership isn’t just about the work you do. It’s about the people you prepare and the systems you leave behind.
By working on your own readiness and developing others’ readiness at the same time, you ensure that when the season of transition comes, your organization is ready — not scrambling. Just as a wise farmer plans not only for this season’s yield but for next year’s soil and the next generation’s field hands, leaders must think beyond their own tenure. The goal isn’t just a good harvest today — it’s a sustainable cycle that continues long after they’ve stepped away from the field.
If you’re always harvesting alone, you’ll always be harvesting alone.
