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One-on-one questions to ask your team

The best one-on-one questions are open, specific and asked consistently. Pick one or two from the group that fits this week, not twenty at once, and spend most of the meeting listening to the answer.

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How to use these questions

Pick one or two per meeting, based on what's going on. Ask, then wait. The first answer is usually the polite one; the second, after a pause or "say more about that", is usually the real one.

Rotate through the groups over a month so you aren't only ever talking about tasks.

To open the meeting

5 items
  1. What's on your mind this week?
  2. What do you want to make sure we cover today?
  3. What was the best part of your week? The hardest?
  4. How's your workload, somewhere between bored and drowning?
  5. Anything from last time you want to follow up on?

Priorities and blockers

6 items
  1. What's the most important thing you're working on right now?
  2. Is anything slowing you down that I could help remove?
  3. Are you clear on what matters most this month?
  4. Is there a decision you're waiting on from me or someone else?
  5. What are you working on that you think doesn't matter?
  6. If you could drop one thing from your plate, what would it be?

Feedback for you, the manager

6 items
  1. What's one thing I could do differently to help you?
  2. Is there anything I do that gets in your way?
  3. How do you prefer to get feedback from me?
  4. Was there a recent decision you disagreed with?
  5. Do you have what you need from me to do your best work?
  6. What should I keep doing?

Growth and career

6 items
  1. What skill do you want to build this year?
  2. What kind of work gives you energy? What drains it?
  3. Where do you want to be in two years? How can this role help?
  4. Is there a project you'd love to be part of?
  5. What's something you've learned recently?
  6. What would make you consider leaving?

The team

5 items
  1. How do you feel the team is working together right now?
  2. Who on the team has helped you lately?
  3. Is there anything on the team I might not be seeing?
  4. What's one thing we could change about how the team works?
  5. Do you feel comfortable disagreeing in team meetings?

How they're doing

Work-framed questions that leave room to share without pressure.

5 items
  1. How are you feeling about work lately?
  2. Is your workload sustainable right now?
  3. What's taking more energy than it should?
  4. Is anything outside work affecting work that you'd like me to know about? You don't have to share.
  5. What would make next week better?

For a new hire

5 items
  1. What's been surprising so far, good or bad?
  2. What's confusing that nobody has explained?
  3. Who has been most helpful? Who should you meet next?
  4. What did your last team do well that we should try?
  5. How are you feeling about the pace of ramping up?

For someone who's struggling

5 items
  1. How do you think the last few weeks have gone?
  2. What's getting in the way of [specific goal]?
  3. What would help most right now: more time, more clarity, or more support?
  4. What does a good week look like for you next week?
  5. How can I check in on this in a way that's useful, not stressful?

Questions to skip

  • "Any updates?" It invites a status report. Ask what's in the way instead.
  • "Is everything OK?" It gets "yep" every time. Ask something specific.
  • Rapid-fire lists. Five questions in a row gets five short answers. Ask one and wait.
  • Leading questions. "You're fine with the new deadline, right?" isn't really a question.

Get past "it's fine" with Lauren

LaurenExample text thread

every 1:1 with one of my reports goes: me 'how's it going?' him 'good.' then silence

"how's it going" is basically a greeting, so he's answering a greeting

try one specific question and then actually wait, even when it's awkward. like: "what's taking more energy than it should right now?"

and if he still says nothing?

then try a different door next week: "what's one thing I could do differently?" sometimes it takes a few weeks of you asking for real before people answer for real

An illustration of how a conversation with Lauren can go, not a real client's messages. Lauren is a real coach. You're texting an AI trained on her coaching.

Ask the question that matters this week.

Text Lauren what's going on with someone on your team. She'll help you pick the question and plan the follow-up.

Your first text

Hi Lauren! I want better questions for my one-on-ones.

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Frequently asked questions

What are good one-on-one questions to ask employees?

Open, specific questions: "What's slowing you down that I could help with?", "What's one thing I could do differently?" and "What skill do you want to build this year?" Ask one or two per meeting and listen.

How many questions should I ask in a one-on-one?

One to three. The goal is a real conversation, not an interview. Follow-up questions like "say more about that" matter more than the list.

What questions should I ask my manager in a one-on-one?

"What are you most focused on this quarter?", "How can I make your job easier?", "What would you need to see from me for the next level?" and "Is there anything I should be doing differently?"

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