How Will You Know It's Time?
This article is part of Finding the Words, a newsletter that delivers practical insights on the day’s issues.
I’ve always admired the leaders who know when it’s time to step aside.
Perhaps because I’ve seen what the opposite can do to an organization: When leaders of social change organizations become the roadblocks to change, when they refuse to step aside, and when they don’t take the necessary steps to prepare the leader behind them.
I’ve seen what happens to an organization’s culture, impact, and focus—and how devastating it can be to an organization when a leader holds on too long. Perhaps it is not all that different from what we see playing out on a national stage right now.
It’s natural to wonder why leaders have difficulty knowing when it’s their time to let go.
I suspect you can relate on some level.
Leaving a role—any role—that has been ours for some length of time can be difficult. Leaving can be particularly challenging for people who have made a lasting impression in their community and who have come to see their identities wrapped up in their organization.
Leaving can be the hardest decision a leader will ever make.
And yet, every single leader will leave their post at some point.
Still, very few leaders plan effectively for it. Very few are willing to let go or to see the signs that their time at the top may be coming to an end. And very few know how to communicate effectively or transparently through such a transition.
In recent months, I’ve witnessed a nonprofit leader and dear friend wrestle with their own decision of whether to stay or go. I’ve seen them internalize feedback from their colleagues, consider their future, and ultimately recognize that the organization is ready, strong, and positioned for a new chapter—with their next leader.
This leader’s process was brilliant, inclusive, and thoughtful. They weighed risks and impact, and they were willing to look holistically at the organization—removing people from the equation just long enough to see that the organization could go on effectively without them.
Yes, it can be hard to let go—of a role or even key responsibilities— but it can help to remember that our identities are more than the jobs we hold.
When leaders at the top of a team step aside—for a day, a brief sabbatical, or through a leadership transition—they can do what no one else in their organization can: They create opportunities for people around them to thrive. They can create pathways for future leaders. And they can contribute to the long term wellbeing and sustainability of the organization.
And sometimes, the art of letting go can model leadership at its best.
Knowing when to step aside can be difficult, but it can be made easier by asking one key question: Am I prepared to let go?
Bottom line: Knowing when to lead and when to make room for others is one of the single greatest leadership skills. Don’t wait until it’s too late to start practicing it.
This post is part of the Finding The Words column, a series published every Wednesday that delivers a dose of communication insights direct to your inbox. If you like what you read, we hope you’ll subscribe to ensure you receive this each week.
