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One-on-One Questions for Remote Managers to Ask
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?
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?
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?
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?
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?
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?