Twelve questions that make one-to-ones better

A good one-to-one lives or dies on the questions you ask. Most managers run the same three on autopilot (“how’s it going, any blockers, anything from me?”) and get the same shallow answers. Here are twelve that go deeper, grouped by what you’re trying to surface.

To open the door

Start wider than “how are you.” That question has a default answer (“fine”) and most people give it without thinking. Try one that’s harder to deflect.

• “What’s taking up the most space in your head right now?”
• “What’s gone better than you expected this week, and what’s gone worse?”
• “If we hadn’t scheduled this, what would you have wanted to talk about?”

The third one is my favorite. It quietly hands the agenda to them, which is whose meeting this is supposed to be.

To find the real blocker

“Any blockers?” gets a no, because people don’t think of half their friction as blockers. They think of it as just how things are. Better questions name the friction for them.

• “What’s the most frustrating part of your week?”
• “Where are you waiting on someone or something?”
• “What would you do if you had an extra half-day this week?”

That last one is sneaky and useful. The answer tells you what they’d protect if they could, which tells you what’s getting crowded out.

To grow the person

These are the questions managers skip when they’re busy, which is most weeks. They’re also the ones people remember.

• “What’s a skill you want to be better at six months from now?”
• “What’s something you’re doing now that you’ve outgrown?”
• “When did you last feel stretched, in a good way?”

The “outgrown” question often surfaces a delegation opportunity for both of you. The thing boring them might be exactly the thing someone more junior would kill to learn.

To get feedback on yourself

The hardest questions to ask, and the most valuable, point back at you. You have to actually want the answer, and you have to react well when it comes, or you’ll never get a real one again.

• “What’s one thing I could do differently that would help you?”
• “Where am I slowing you down?”
• “Is there anything you’ve been hesitant to tell me?”

Don’t fire all twelve in one sitting. Pick two or three. A one-to-one is a conversation, not an interrogation.

The part that isn’t the question

The question only opens the door. What people actually need is for you to stop talking once they walk through it. The reflex to jump in with advice, to fix, to relate it back to your own experience, is what turns a good question into a wasted one. Ask, then wait. Let them think out loud. The silence after a real question is where the useful stuff lives.

Pick one question from this list you’ve never asked, and try it in your next one-to-one. Then count to five before you say anything back.