Want to learn how to lead? Lead.

This past weekend, I had the honor of spending the afternoon with my son. Those who know me well, may know that this by itself is not trivial.  Anyway, in our conversation, he shared a story with me that blew my mind.

During his high school years, my son spent a semester in a military-style program.  About halfway through the program, the directors had a process for selecting students (cadets) to lead each platoon for two weeks.  The expectation was that those who had demonstrated various desirable skills would be selected to lead the platoon. 

He shared how the cadets discussed amongst themselves who would be selected for the next opportunity, and why. Most expected the role to go to the clear standouts—the talented, the confident, the skilled. Quiet debates broke out among the teens about who "deserved" the honor. But what they all agreed on was that (I’m making up a name) Gary would definitely NOT be chosen.  Even Gary agreed that he was definitely not a leader. He didn't have the skills, the knowledge, or even the apparent desire to lead.

So then, the day comes to select the first leader of the platoon. And the story wouldn’t be a story if they didn’t select Gary!  Gary?  Yes, the same! Of course, the cadets were all confused. They wondered: if we are here to develop leadership skills, why are we not honoring the ones who are demonstrating those skills?  How on earth could they pick Gary?

So they asked the sergeant, “Sir, we are all surprised that you picked Gary to lead.  He has no skills, he screws up all the time. How in the world did you pick him?”

The sergeant responded, “How is he going to learn to be a better leader by not leading?”

Mic drop. Let that simmer for a minute.

So my son went on to say that Gary led. He struggled. He failed. But then he learned, adjusted, and tried again. Disaster after disaster, each time just a bit less catastrophic, until—slowly—it got better. Not perfect. Better.

What’s the lesson here:

Growth demands action and resilience: True learning comes from doing, failing, and trying again, not from waiting to be ready.

Great leaders are forged through grace: Everyone, even (especially) leaders, will stumble. Extend the same grace you would hope for yourself.

Don't wait to be perfectly competent: The path to excellence starts before you feel fully prepared.

Eventually others had opportunities to lead the platoon. The other cadets were not left out, but they learned an incredible life lesson watching Gary learn how to lead. A lesson that they are now teaching us, or maybe it's just me.

Who Is Your Gary?

Ask yourself: In your team, family, or circle, who might be a “Gary”—overlooked, underestimated, maybe even discounted by themselves? What if you gave them the opportunity to try, to fail, and to grow? Imagine the ripple effect if every leader championed progress over perfection.

Lead boldly. Look for the Garys. And never underestimate the power of believing in someone before they believe in themselves.