The Best Question I've Asked in a 1:1 This Week

I've been doing 1:1s for a long time. I have a running list of questions I rotate through — about workload, growth, blockers, team dynamics. Most of them are good. Some of them are great.

But this week I asked one that has made a big different already.

"If you were sitting in my seat as the CEO, what would you be doing differently?"

I wasn't prepared for what came next.

Why I Asked It

I've been thinking a lot lately about the gap between what leaders think is happening inside their organization and what's actually happening. We recently did an eNPS and I've been reflecting a lot. The higher up you are, the harder that signal is to find. People filter. They soften. They tell you what they think you want to hear, not because they're dishonest, but because the power dynamic makes it feel risky to say the real thing.

So I've been looking for questions that cut through that. Questions that give people permission to be direct.

This one does it by flipping the frame entirely. I'm not asking "how are you doing" or "what do you need from me." I'm handing them the keys and asking what they'd do with them.

It changes everything.

What Happened When I Asked It

The person I was in a 1:1 with this week paused. And then they told me.

Thoughtfully. With the kind of clarity that only comes when someone has actually been paying attention and finally has a real opening to say what they see.

What they shared wasn't groundbreaking. It wasn't a strategy overhaul. But it was real. Specific, grounded, and genuinely useful. Something I can put into practice starting next week. The kind of feedback that doesn't make it into performance reviews or town halls or Slack. The kind that lives in people's heads until someone finally asks.

Why This Question Works

Most feedback questions are too safe. "What could we be doing better?" is easy to dodge. "Any concerns I should know about?" is even easier. The answer is almost always no.

This question is different for a few reasons.

It removes the hierarchy for a moment. You're not asking them to give feedback up the chain. You're asking them to inhabit the role. That's a fundamentally different cognitive act. It invites perspective-taking instead of critique, which makes the answer feel less like complaining and more like problem-solving.

It signals that you're actually open. Asking this question is an act of vulnerability. It says: I don't have all the answers. I know there are things you can see that I can't. Tell me. People respond to that differently than they respond to a generic "open door policy."

It gives them ownership. When someone answers this question, they're not just venting. they're thinking like a leader. That's useful for them, not just for you. Some of the best career development conversations I've had have started here.

What I Do With the Answers

I listen first. I don't defend, explain, or contextualize in the moment. That's the fastest way to make sure they never answer honestly again.

After the 1:1, I write down what they said. Not to log it or track it — just to sit with it. Some of it I act on. Some of it I disagree with. Some of it I need more context on. All of it tells me something.

The most important thing isn't whether every answer produces a change. It's that the person across from you knows that when they tell you the truth, something happens. Even if that something is just: I heard you. I thought about it. Here's where I landed.

That's the feedback loop that builds trust. And trust is the whole game.

Try It This Week

If you lead people — a team of two or a team of two hundred — try this question in your next 1:1.

Don't set it up too much. Don't make it a big moment. Just ask it like you mean it, and then get quiet.

You might not love everything you hear. That's kind of the point.

The question isn't "tell me what I'm doing right." It's "what do you see that I might be missing?" 

If you try this and want to share what you heard — or if you have a go-to 1:1 question of your own — I'd love to know.