The Question Behind the Question
We ask boys a lot of questions. "Why aren't you trying?" "Don't you care about your future?" "What were you thinking?" We ask them with the best of intentions...we want to understand, to help, to get to the bottom of things.
But here's the uncomfortable truth I've learned over thousands of hours working with teenage boys: most of those questions aren't really questions at all. They're statements in disguise. "Don't you think you should…" means do the thing I want you to do. "Why would you…" means I think what you did was wrong. And boys can smell the real intent a mile away.
They're not inquiries...they're judgements dressed up as curiosity, and the moment a boy senses one, the wall comes up.
The shift I want to offer isn't a clever technique, it's a mindset. It's the difference between approaching a boy as a problem to be solved and approaching him as a thinking partner. Compare "Why did you do that?" with "What were you hoping would happen?"
Both seek similar information, but one invites justification while the other invites reflection. Or swap the closed "Did you have a good day?" for the open "What was the best and worst part of today?" The second one requires him to actually think.
The skill isn't in having the perfect script…it's in noticing whether your question is genuinely curious, or quietly loaded.
I remember working with a boy who was struggling badly at school. His teachers were frustrated, his parents were at their wits' end, and every standard question had been fired at him: "Why aren't you trying? Don't you care?" Nothing worked. During a walk together, I asked him something different, "If school could be anything you wanted it to be, what would that look like?" He was quiet for a long time. I waited. And then he started talking...about feeling stupid when he couldn't follow instructions, about being so anxious he'd fail anyway that he'd stopped trying, about wanting to learn but not in the way school taught him.
That one question opened a door that dozens of "why" questions had kept firmly locked. Because it wasn't about blame. It was about curiosity and possibility.
If you want a few things to try this week, start with the questions that invite rather than interrogate: "What's the hardest part of this for you?" … "Help me understand your thinking on that." … "What would help right now?" When a boy seems flat, try "On a scale of one to ten, how are you really going?" and follow it with "What's one thing that might move you to a [next number up]?"
And whatever you ask, resist filling the silence. When he says "I don't know," try "take your time" instead of moving on (the pause is often where the real answer lives). Count to three before you respond. Say "tell me more about that" rather than rushing to relate it to yourself.
These are small moves, but in a classroom or a corridor conversation, they change everything.
The reason this matters goes beyond any single exchange. The questions we ask boys, over time, become the questions they learn to ask themselves:
What matters most to me here?
What am I really feeling?
What kind of person do I want to be?
In a world that constantly tells boys what to think, our genuine questions teach them how to think.
So perhaps the most powerful question is the one we ask ourselves before we open our mouths...
...am I approaching this with real curiosity about who this young person is…or with an agenda I want him to accept?
I get this wrong more often than I'd like to admit. But when I can honestly answer "genuine curiosity," the questions take care of themselves.