On Asking Why: A Pilot, a Marine, and a Stoic Walk into a Meeting
Years ago, I took over as my unit’s executive officer (XO). The outgoing XO was an infantry officer. I was an aviation officer.
If you’re familiar with the Marine Corps, you can probably already imagine the potential for friction. If you’re not, here’s a quick primer: when it comes to aviation Marines and infantry Marines, there’s a bit of military Odd Couple energy — one stays in the lane, the other asks if we could repaint the road. Neither is more right than the other. Just… different.
During our turnover, he walked me through the role — “This needs to be done this way,” and “That needs to be done that way.” And each time, I had the audacity to ask:
“Why?”
After about fifteen minutes of this back-and-forth, he lost it.
“You’d make a terrible infantry officer!”
I didn’t miss a beat. I grinned and asked…
“Why?”
He glared.
“THAT’S WHY!!”
Touché.
I had to laugh. But then he followed up with a more serious point:
“You ask too many questions. When I tell you to take the hill, take the hill. No questions asked.”
Now, I respect where he was coming from. There are rare moments when a leader needs fast, decisive, no-time-for-discussion action. But that wasn’t one of those moments. And let’s be honest — most of the situations we face in life and leadership aren’t, either.
The truth is: It’s okay to ask “why.” In fact, it’s essential.
If anything, asking “why” is a mark of engagement, not defiance. It’s how we build clarity, creativity, and better decisions. It’s also how we practice humility — something the Stoics considered foundational to wisdom.
Mavericks and questioners might slow you down at times, but they also open new doors. Mavericks show you what’s possible. Questioners help you see what you’ve missed. They often think differently — right-brain, creative, unorthodox — and they’re offering that perspective to the team. So don’t squash it. Cultivate it.
And here’s a little secret:
One of the best ways to create space for those insights is humor.
Humor disarms defensiveness. It makes people feel safe enough to speak up. It helps us shift from “That’s a dumb question” to “Wait… what if they’re onto something?”
So the next time someone challenges the plan or throws out a strange idea, don’t just answer with data — answer with curiosity. Maybe even a joke. And see where the conversation goes.
Because sometimes, the difference between “terrible” and “terrific” lies in the questions we’re bold enough to ask — and the laughs we’re willing to share.“If someone is able to show me that what I think or do is not right, I will happily change, for I seek the truth, by which no one was ever truly harmed.”
— Marcus Aurelius