Twenty Questions for your 1:1s

zoom call

You sit down for a chat with someone on your team. You get through the pleasantries, the small-talk, the status, and you run out of things to say. It happens to even the most curious and high-EQ people. It happens to me, and I have probably had 10,000 one-on-one meetings in my career.

When you hit that moment where neither of you has anything to say, it is very tempting to just say, “Ok then! Let’s talk next week.” giving you both time back into your day. If this happens occasionally, it is not a severe problem. However, if you find it happening more often than you would like, it is good to keep some prompts handy to move into deeper topics that might prompt a valuable conversation.

Here are twenty questions that you might find helpful if you get stuck at the surface level or run out of things to discuss in your one-on-ones:

  1. What is more challenging in your day-to-day work than it should be?
  2. What is the most fulfilling thing that has happened this week?
  3. Who on the team has been really impressing you lately?
  4. What are you looking forward to in the next six months? Why?
  5. What haven’t you told me that I probably should know?
  6. What is one thing that you miss from your last job/team?
  7. Who on the team are you most worried about?
  8. If there is one thing I could change about your role today, what would it be?
  9. Who on another team do you most enjoy working with?
  10. What do you wonder about?
  11. How would you change the company’s strategy?
  12. What is the product or feature that we should build next?
  13. When do you feel the most satisfied at work?
  14. What is your least favorite part of your job?
  15. What percentage of your work time do you think you are in a flow state?
  16. What is the one meeting that you would add to your calendar?
  17. What is the one meeting that you would remove from your calendar?
  18. What do you wish that I did differently?
  19. What should I keep doing?
  20. When am I the most helpful?

If you don’t like any of these questions, you can create your own list in a few minutes. You are looking for a question that gets the other person to think a bit, share a bit more with you, and hopefully give you an avenue for deeper discussion.

Have other questions that you like to use? Please add them in the comments!

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