I moved to Auburn, AL, in 2010 to work at Auburn University. I inherited a much smaller staff than where I’d worked before, so I believed managing them would be like riding a bike.

I was wrong.

As expected, some people were on board, some weren’t. Several were curious, and a few didn’t care. Some quit; most stayed. Like every team I’ve led, there were individuals who made my job easier, harder, entertaining, or just showed up. One person from that staff stands out today as someone who helped reshape how I view leadership.

That young man’s name was Kevin Littleton.

I’m known for asking challenging questions, but in 2010, I met my match. Kevin was a student employee with no fear of challenging “the boss.” Each time Kevin saw me, I could see his wheels turning on what he was going to ask. If I opened the door with my left hand, he would’ve probably said, “Why didn’t you use your right hand?”

Kevin challenged everything.

Conversations with Kevin were like full-body workouts. He joined me on 30-mile bike rides, met me for marathon conversations at Panera Bread, and frequently waved me over for “a quick question” while confined to his station at work.  

Kevin’s questions were rarely due to a lack of understanding. Kevin is extremely intelligent. I believe Kevin is the type of person who won’t let you get away with spewing nonsense out of your mouth without being able to back it up.

Kevin’s coworkers thought I should fire him for being argumentative, but I always loved our back-and-forth debates. He made me think more carefully about my words before asking the staff to do something.

Fifteen years later, Kevin is thriving—a husband, father, and servant-hearted professional. He sells medical devices for Avita Medical, leads advancement for The Oaks Collaborative, owns a cattle farm, and co-owns a property and investment business.

Kevin doesn’t know this yet (though he’ll probably argue with me about it), but he made me a better supervisor and a better man, who better understands the value of disagreement, as quoted by Drucker above.

Leading well isn’t surrounding yourself with “yes men,” but valuing people who challenge you to prove it. I am grateful that Kevin is a Sharper Leader who helps sharpen me and others.