One-on-One Questions for Remote Managers to Ask

7 minutes, 9 links


Updated March 23, 2023

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It’s helpful to have a well of options you can turn to regularly to keep your one-on-ones fresh and find new ways to prompt interesting or useful answers from your team. Asking deeper questions leads to greater trust and intimacy than small talk does; a key pattern to foster in developing close relationships is “sustained, escalating, reciprocal personalistic self-disclosure.”*

Rather than ending a one-on-one early when an agenda is light, you can ask your direct report one or two of these questions, ideally getting more personal and reflective over time.

Productivity and Career

  • When did you recently get an opportunity to learn and grow? How can we create more of those?

  • Have you seen someone else doing something you felt worked really well? What was it?

  • What should I know about you that would help me support you better?

  • What are you doing here that you feel is most in line with your long-term goals?

  • What are your biggest time wasters?

  • If you could be proud of one accomplishment between now and next year, what would it be?

  • Is anything holding you back from doing the best work you can do right now?

  • Is there a project or area outside your current role where you feel you could be contributing?

  • Which areas make you feel like your hands are tied or you are unable to reach your full potential?

  • If you were to create your ideal position, how would it differ from what you are currently doing?

  • At what point in the past week were you most frustrated with or discouraged by your work? What can I do to help you manage that?

Seeking Feedback

  • Would you like more or less direction from me?

  • Would you like more or less feedback on your work? If more, what additional feedback would you like?

  • If you were coaching me to have a greater positive impact, what would you tell me?

  • What can I tell you about myself that might make it easier to understand me and work with me?

  • Have you seen a product or initiative at another company recently and thought to yourself, ‘I wish we’d done that’?

  • What vibrations (news, rumors, dynamics) are you picking up that you think I should know about?

  • What’s our biggest oversight, and how do we resolve it?

  • What do you feel is our biggest risk right now?

  • What was the most useful part of our conversation today?

  • What are you worried about right now?

Building Relationships

  • How’s life?

  • What’s going on for you these days outside of work?

  • What is something you’ve done that you’re proud of?

  • What was something you were scared of as a child? Have you overcome it?

  • What fictional character do you most identify with?

  • Would you rather be known or unknown? Why?

  • What hot topic usually turns into an argument for you?

  • Do you have a motto or personal mantra?

  • What’s on your bucket list?

Transition and Change Questions

  • Imagine it’s two years from now, and things have gone well: What has been your role in that? What does your role look like?

  • What are you worried might happen if you made this transition?

  • What will happen if you don’t take this step?

  • What would need to change for you to get to a point of “let’s do this” or “I don’t want this”? What information do you need?

Team Dynamics

  • How would you say we’re doing at working together as a team? What makes you say that?

  • What do you think the rest of the team is most concerned about? (People may also share what they are personally concerned about; this framing makes it easier to share.)

  • Who on the team is doing really well right now? (Also listen for names that don’t come up.)


  • Are there any decisions you’re hung up on?

  • I’ve noticed you’re a little quieter than usual. Is there anything you’d like to talk about?

  • Do you feel stretched thin? (This wording is useful to measure subjective stress, not objective workload.)

  • What, if anything, did you used to do that you find you don’t have time for right now?

  • What is your takeaway from this discussion? (This is especially helpful to get to action steps from a thorny issue.)

  • In our last one-on-one you mentioned you were frustrated by X and wanted to try Y as a solution. How has that been going?

  • During this meeting you’ve mentioned that you’d like to pursue X. What steps can you take toward that before our next one-on-one?

  • What could we change about work that would improve the rest of your life?

Conflict Resolution

  • What does your ideal outcome look like? (Could be about a specific conflict that’s come up, or approached hypothetically.)

  • What’s hard for you in getting to that outcome?

  • What do you really care about?

  • What’s the worst-case scenario you’re worried about?

Getting Deeper

  • Are you afraid of anything at work?

  • I’ve noticed that our last several one-on-ones have stayed pretty surface. What are your honest impressions of this meeting? What could we be doing differently or better?

  • What’s something you used to strongly believe in that you no longer do today?

  • Before making a telephone call, do you ever rehearse what you are going to say? Why?

  • What are three things you and I appear to have in common?

  • What do you feel most grateful for in your life?

  • Take four minutes and tell me your life story in as much detail as possible.

  • If you could wake up tomorrow having gained any one quality or ability, what would it be?

  • Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?

  • What do you value most in a friendship?

  • What, if anything, is too serious to be joked about?

Further Reading for Remote One-on-Ones

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