My favorite question to ask potential candidates when interviewing them for a head coaching or assistant’s position was:

What’s the Biggest Mistake You’ve Made Professionally?

This question is revealing. Candidates who could openly discuss their mistakes and the lessons they learned demonstrated humility, self-awareness, and a growth mindset. These are qualities I wanted on my team. If they’ve made the mistake before and learned from it, chances are, I wouldn’t have to deal with it on my watch. On the other hand, candidates who avoided the question or struggled to identify a mistake raised a red flag. It suggested a fixed mindset or a lack of reflection—traits that can hinder growth in a leadership role.

Trump asked Obama This Same Question on Inauguration Day in 2016

Since 1847, the President and President-elect have shared a historic ride to the inauguration. It’s a symbolic tradition of transition, but it’s also a moment for dialogue. Eight years ago, during this ride, Donald Trump asked Barack Obama a profound question:

“What was the biggest mistake you made as President?”

This isn’t just a great question; it’s a masterclass in leadership and the growth mindset. By asking it, Trump acknowledged an essential truth: mistakes aren’t failures; they’re lessons. Even more, by learning from others’ mistakes, we can grow faster and make fewer missteps of our own. This mindset isn’t just for presidents—it’s critical for leaders at all levels.

Mistakes: The Best Teachers

Great leaders understand that no success story is complete without a few mistakes along the way. Mistakes are inevitable, but how we respond to them defines our growth. A growth mindset allows us to:

Learn and Adapt: Treating mistakes as feedback, not failure, shifts the focus from blame to growth. Each misstep becomes an opportunity to improve.
Foster Resilience: Leaders who embrace their mistakes develop the ability to bounce back stronger. They model resilience for their teams.
Prevent Repetition: Reflecting on what went wrong ensures that the same mistake isn’t made twice.

The Worst Mistake I Made as an AD/Head Coach…

In my first year of coaching at Paducah High School in West Texas in 1999, I learned a valuable lesson about perception versus intent. Paducah is a small town of around 1,000 people, and back then, the high school had about 120 students. Basketball was a point of pride for the community, with the team having won state championships in 1996 and 1997.

When I arrived in Paducah that May, I barely knew anyone in town, let alone the members of the team. The school had two gyms: the main competition gym and an auxiliary gym that also housed our weight room. During the summer, the auxiliary gym was open Monday through Friday and had essentially become a rec center for the town. Adults would use the space to play basketball during the day, often leaving behind trash, spilled drinks, and general disarray. Meanwhile, the weight room, which was critical for our athletes, felt like an afterthought in this environment.

I didn’t have the time or energy to manage this chaos, and I needed a solution. My idea? I took down the rims in the auxiliary gym and posted a note on the door:

"High School athletes—the competition gym is open and available for you to shoot in AFTER you lift weights."

To me, this seemed like a reasonable approach. I even got approval from my sole supervisor, the superintendent, before implementing the change. However, the town of Paducah saw it differently.

All they saw was this: "Jackson is going to be anti-basketball."

That was not my intent, but perception is everything in a tight-knit community where basketball had recently won two state titles. This decision created a significant hurdle I had to overcome. I inadvertently alienated the town and sent the wrong message about my priorities. Looking back, I realize I should have come up with a better solution—one that maintained order without undermining the town’s trust in me or the basketball program.

This mistake taught me the importance of balancing intent with perception, especially in a community where sports play such a central role. It was a hard-earned lesson, but one that shaped how I approached challenges and communication moving forward.

Learning from Others’ Mistakes

While learning from your own mistakes is valuable, learning from others’ mistakes is even better. It saves time, energy, and resources. As a leader, one of the most powerful tools you have is curiosity. Ask those who have "been there and done that" about their experiences. Questions like:

“What would you do differently if you could go back?”
“What were your biggest challenges in this role?”
“What did you learn from your toughest moments?”

These questions open the door to wisdom that can guide your decisions and help you avoid common pitfalls.

The Key Takeaways for Leaders

To foster a growth mindset in yourself and others, keep these principles in mind:

Be Curious: Ask thoughtful questions and seek feedback from those with more experience. Their insights can save you from making avoidable mistakes.
Reflect on Mistakes: Regularly review your own actions and decisions. What worked? What didn’t? What will you do differently next time?
Create a Safe Space for Learning: Encourage your team to view mistakes as opportunities. When people feel safe admitting their errors, they’re more likely to grow.
Model Growth: Be open about your own lessons learned. When leaders share their vulnerabilities, they inspire others to embrace growth.

“Sometimes We Win, Sometimes We Learn.”

Whether you’re leading a nation, a team, or a classroom, adopting a growth mindset is key to success. Mistakes are part of the journey, but they don’t define you. What does define you is your willingness to learn—not just from your own experiences but from those who came before you.

So, the next time you have the chance, ask this powerful question:

Seek Out Someone With Experience You Trust and Ask Them, “What’s the biggest mistake you’ve ever made?”

You’ll be surprised how much you can learn from the answers. After all, winners and learners both know: growth never stops.