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One-on-One Questions

30 items

Most managers have four one-on-one questions and exhaust them by month three, after which the meeting becomes a status update that a message could have covered. Draw one before each session and the conversation goes somewhere the agenda would not have taken it. Thirty questions ranging from the practical to the ones that need a bit of trust already in place. Do not draw more than two per session. This is a conversation, not an interrogation.

What's on the Wheel

All 30 entries that will be loaded onto the spinning wheel

1What is the most frustrating part of your week?
2What do you want to be doing in two years?
3What could I be doing better?
4What is unclear right now?
5Who on the team do you learn the most from?
6What would you change about how we work?
7Is anything getting in the way that I could remove?
8What are you proud of that I might have missed?
9What skill do you want to build next?
10How is your workload, honestly?
11What feedback have you not had that you want?
12What part of your job would you happily drop?
13What part would you do more of?
14Is there anything you are worried about?
15What do you wish we did differently as a team?
16What was the best day you have had at work recently?
17Where do you feel stuck?
18What are you curious about?
19What would make your next month better?
20What decision would you like more say in?
21Who deserves recognition that they have not had?
22What is something you disagree with and have not said?
23What do you need from me in the next two weeks?
24How do you like to receive feedback?
25What would make you consider leaving?
26What is working better than you expected?
27Which meeting could you drop without loss?
28What would you like to learn from someone here?
29What is one thing we should stop as a team?
30What question should I be asking you?
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