Handing Over the Reins

Perhaps one of the greatest signs of healthy leadership is being excited about what someone else might do differently.

There is something strange about handing over something you have led for a long time. For years, you wake up thinking about it. You carry its problems home with you, celebrate its successes, worry about its people, and spend countless hours imagining what it might become. You make decisions—some good, some you would probably make differently today. You push when you think the organization needs pushing, listen when you realize you need to understand more, and adjust when the path you chose doesn’t quite lead where you expected. Somewhere along the way, the organization becomes intertwined with your own story. And then, eventually, someone else takes the reins.

This month, I have the opportunity to experience exactly that. After five years leading a school community I care deeply about, I moved into a different role within the same organization. It has given me an unusual vantage point. I haven’t really left. I still walk the same hallways, see many of the same people, and remain deeply invested in the success of the organization. But the community I once led is no longer mine to lead. Someone else now gets to decide what comes next, and I am discovering that there is something both humbling and incredibly exciting about that.

The Work Is Never Finished

Leadership transitions have a way of reminding us of something that can be difficult to see while we are sitting in the leader’s chair: no single leader can take an organization everywhere it might go. We each move it forward in ways shaped by our own strengths, experiences, relationships, and ways of seeing the world. We leave our mark, but we also leave possibilities unexplored. That isn’t a limitation of leadership so much as part of its nature. Sometimes an organization needs a new set of eyes, a different collection of strengths, and another person imagining what might come next.

When I look back on my years as a principal, I am incredibly proud of what we accomplished together. There are programs that didn’t exist before, changes in culture, new ways of thinking about learning, traditions that became part of the fabric of the community, and difficult decisions that ultimately made us stronger. There are moments when I can look back and clearly see that the school was different because of the work we did together.

But I can make another list just as easily. There were ideas that remained ideas, problems we improved but never completely solved, conversations I wish I had started sooner, and initiatives that never quite became what I imagined they could be. I suspect most leaders who have stayed in a position for any meaningful amount of time carry a similar list. We know what we accomplished, but we also know the distance between the organization we inherited and the organization we imagined it could someday become.

It is tempting to look at that unfinished work with regret. If only I had another year. If only I had pushed harder. If only I had figured that problem out sooner. But perhaps that misunderstands the nature of leadership. Maybe the goal was never to finish the work. Organizations are living things, constantly shaped by changing people, circumstances, needs, and possibilities. If we believe our job is to complete the organization before handing it over, we will never be ready to leave.

Someone Else Has What You Don’t

Every leader brings a particular collection of experiences, instincts, relationships, passions, strengths, and blind spots into a role. Those things inevitably shape the organization we lead. There were areas I could move forward because of who I am as a leader. There were probably other areas that were more difficult to move forward for exactly the same reason. We like to imagine that good leaders can become whatever an organization needs at any given moment, but there are limits to that idea. We can learn and grow, but we remain ourselves.

That is one reason leadership transitions can be so powerful. The person who comes next does not need to be a continuation of the person who came before. In fact, perhaps the organization is better served when they aren’t. A new leader notices things the previous leader stopped noticing. They ask questions that haven’t been asked in a while. They build relationships differently and bring experiences that allow them to see old challenges through a new lens. Something I struggled to move forward for years may be exactly the kind of challenge that plays to the next leader’s strengths.

There is something freeing about recognizing that. The unfinished pieces of our leadership do not necessarily represent failures. Some of them may simply be work that needs a different leader, at a different moment, with a different set of strengths. There are things I wanted for the community I led that I may now get to watch someone else accomplish. Rather than diminishing what came before, that possibility makes me even more hopeful about what comes next.

From Ownership to Stewardship

Of course, embracing that possibility requires something from the outgoing leader: we have to let go. That sounds obvious until you have spent years saying “my school,” “my team,” “my program,” or “my community.” The language comes naturally, but it can quietly reinforce the idea that the organization somehow belongs to us. It doesn’t. Leadership is stewardship. We are entrusted with something for a period of time, asked to care for it and move it forward, and eventually expected to hand it to someone else.

That handover becomes more complicated when you remain nearby. In my case, I still work within the same organization, which means I don’t have the clean separation that often comes with a leadership transition. I could easily continue to have opinions about how things should be done. I could explain the history behind every decision or find subtle ways to protect the things I built. I could become the person who says, “Well, when I was principal…” far more often than anyone needs to hear it.

But being nearby does not give a former leader permission to continue leading from the shadows. In fact, it may make the responsibility to step back even greater. A new leader deserves the same opportunity we once had: to listen, learn, experiment, make decisions, make mistakes, build relationships, and ultimately make the role their own. The most useful thing an outgoing leader can offer may be context when it is requested, support when it is needed, and enough space for something new to emerge.

I was fortunate to have that modeled for me. The principal who led the school before me retired but remained in the area, and throughout my five years in the role, she was one of my biggest cheerleaders. She cared deeply about the school, but she never made me feel as though I was simply looking after something that still belonged to her. She gave me the space to lead it in my own way while continuing to celebrate the community and its successes. Looking back, I appreciate even more what a gift that was.

Now the roles have shifted again. There is a new principal leading the community, I am still nearby in a different role, and my predecessor is still cheering us on. I find myself looking forward to the day, hopefully soon, when the three of us can sit down over a cup of coffee: three people who have had the privilege of leading the same school at three different moments in its story. Each of us brought—or will bring—something different to it. Each inherited something from the person before us, added something of our own, and eventually entrusted it to someone else.

There is something wonderfully reassuring about that continuity. The school was never any one of ours. We simply each had the privilege of caring for it for a while.

Rethinking Legacy

Leadership conversations often turn eventually to legacy. I have always been a little uncomfortable with the word because it can make leadership sound as though we are supposed to build monuments to ourselves. We point to the programs we started, the traditions we established, or the systems that survived after we left as evidence that our leadership mattered. There is nothing wrong with being proud of those things, but I am increasingly convinced that the healthiest organizations should not spend too much time trying to preserve a former leader’s fingerprints.

Perhaps legacy is less about what remains unchanged and more about what is strong enough to evolve. Maybe it is developing people who no longer need you, building systems that can be improved without you, and nurturing a culture confident enough to welcome a new leader without feeling that its identity is under threat. Perhaps one of the greatest compliments to our leadership would be to return years later, see something thriving that looks completely different from what we would have created, and be genuinely delighted by it.

That requires a particular kind of humility. We have to believe that our contribution mattered without believing that our way must endure. We have to be able to look at something the next leader changes and resist interpreting the change as a judgment on what came before. Sometimes a new direction doesn’t mean the old direction was wrong. It simply means the organization has reached a different moment.

It’s Someone Else’s Turn

I know the person taking the reins after me will lead differently than I did, and I genuinely hope she does. She brings experiences I don’t have, strengths I don’t possess, and a fresh perspective on a community I have come to know incredibly well. She will see things I stopped seeing simply because familiarity changes our vision. She will ask different questions, develop different priorities, and undoubtedly make some decisions that I would not have made.

I find myself increasingly curious about those differences rather than apprehensive about them. There are things I couldn’t accomplish that she might. There are things I started that she may take much further. There may also be things I built that she eventually decides the community no longer needs. And there will almost certainly be things she creates that I never would have imagined. None of that erases what came before. It is simply what happens when an organization continues to grow.

Perhaps that is ultimately what a healthy leadership transition asks of us. We take the reins when they are handed to us. We hold them with care. We use everything we know and everything we have to move the organization forward during the time it is entrusted to us. We accept that we will leave some things unfinished, because the work of an organization was never meant to be completed by one person.

And then, when the time comes, we hand the reins to someone else—not reluctantly, not hoping they preserve everything exactly as we left it, but with genuine excitement about where they might go next.

Because maybe the final measure of our leadership isn’t how much of us remains after we leave.

Maybe it is how ready we are to see what becomes possible without us.