For a stretch of years fairly early in my career, I had a mentor who almost never answered a direct question directly. I'd come to him with something genuinely stuck, a personnel issue I didn't know how to handle, a budget decision I couldn't reconcile, a family situation colliding with a professional obligation, and instead of telling me what to do, he'd ask me something like, "What do you think happens if you wait a week?" or "Who else in this situation hasn't had a chance to tell you what they see?"
Wanting Answers Instead of Questions
I found this maddening for longer than I'd like to admit. I wanted answers. I was young in the role, anxious about getting things wrong, and I had sought him out specifically because he had decades of experience I didn't, and it felt, honestly, a little withholding for him to sit there asking me questions instead of just handing over the wisdom I assumed he had stockpiled somewhere. There were afternoons I left his office more confused than when I walked in, at least on the surface, still holding the same unresolved problem, just with more questions attached to it than before.
What I didn't understand at the time, and what took me years and eventually becoming a mentor to other people myself to fully understand, is that he wasn't withholding the answer. He was withholding the dependency. If he'd told me what to do every time I walked into his office, I would have gotten good at asking him what to do, and I would not have gotten good at figuring out what to do, which are entirely different skills, and only one of them is actually useful once you're the one running the meeting instead of attending it.
The Staffing Decision That Changed My Thinking
I remember one specific case that crystallized this for me. I had a staffing decision I was agonizing over, someone who was well-liked personally but underperforming in a way that was affecting a whole team, and I wanted him to just tell me whether to let the person go. He asked me instead what I was actually afraid of. Not what I thought the right decision was, what I was afraid of. I sat with that question longer than I wanted to, and eventually admitted that I was afraid of being disliked, not afraid of making the wrong call for the team. Once I said that out loud, the actual decision became almost obvious. It had never really been about the employee's performance data, which I already had and already understood. It had been about my own discomfort with being the person who delivers hard news, and no amount of data was going to resolve that discomfort. Only naming it did.
He could have just told me to let the person go. It would have saved me an uncomfortable half hour of sitting with my own motives. But if he'd done that, I would have executed his decision instead of making my own, and the next time a similar situation arose, without him in the room, I would have been just as stuck as before, because the actual obstacle, my fear of being disliked, would still have been sitting there unexamined, waiting to trip me up again.
Trying to Carry the Habit Forward
I try to carry this forward now with the people I mentor, and I'll admit I'm not as disciplined about it as he was. It is genuinely hard to sit across from someone who is anxious and stuck and simply ask them a better question instead of relieving their anxiety with a quick answer. Every instinct pulls toward being helpful in the most immediate, visible way, which is to just solve the problem for them. But I've come to believe that's often the less generous move, because it trades their long-term capacity for your short-term comfort in the room. Handing someone an answer feels like generosity. Often it's actually a way of avoiding the harder, slower work of helping them build the judgment to find their own.
He passed along plenty of concrete advice over the years too, and I don't want to romanticize the questions into some mystical pedagogy that never involved actual guidance. Sometimes the answer really was just the answer, and he gave it. But the questions were the part that changed how I think, not just what I decided in any single moment, and twenty years later I still catch myself, stuck on something hard, asking myself what he would have asked me instead of what he would have told me. That habit has outlasted almost everything else he taught me directly, which I suspect is exactly what he intended.
