One on One Questions

Good One-on-One questions

What’s one thing we could do for you to help improve the performance of your team?
What’s the biggest thing preventing your team from getting more done, or done better?
How much time do you spend in meetings? Are there any you don’t feel you need to attend?
How much time are you spending on individual work? What about managing? (Are they investing enough in their team?)
If we had budget to get you any one thing for you to make you better at your job, what would you want?
If we had budget for any one thing for your team to be more effective, what would you want?
Am I available to support you when you need it? Why do you say that?

Who do you think is at risk of leaving the company? How could we save them?
Who are your top performers? Why them?
Do you feel everyone on your team is properly compensated based on their performance?
Who on your team is struggling right now? What tactics are you using to help them?
What’s the best idea or suggestion you’ve heard from your team lately?
How do you solicit ideas and feedback from your team? How often?
What’s one thing we should stop doing?
What’s a recent situation where you’d like my advice on how to handle it now or next time?
How did you think [situation] went? How could we improve that together?

What’s one thing I could do to better support you?
What’s the biggest bottleneck or blockers that affects you and your team doing their jobs well?
What would you change if you had my job? Why that?
What do you want to know about my job?
What would you do to help the person replacing you if you had my job?
Is there anything in my job you feel you don’t know that you should?

How is managing your team going for you?
How is you / your team’s workload? Too little, too much, or the right amount?
How do you feel about your balance between doing individual work vs. managing? Do you feel like you’re doing too much or too little of either?
What is your favorite part about being a manager? Why that?
What is your least favorite part about being a manager? How do you handle that?
What do you want to do next in your career? How can I help you get there?
Are you happy in this role? What could make it better for you?
If you could go back to your old job, would you want to? Why?
How do you feel your work/life balance is? What would you want to change, if anything?
How often are you having one on ones? Does that feel like the right frequency for everyone?
What has come up in your one on ones lately that I should know about, or you’d like help with?
When was the last time you praised each of your team members?
Anyone need performance improvement? Why?
Who is close or ready for promotion? For what roles?
Who are the best people on your team? What are they doing well?
How can we help your best people be more successful?
If you had to promote someone to [role x] who would you recommend and why?
Do you feel [team member x] is ready to advance? How can we work together to help them grow?

What do you and your team think of the recent changes?
What tweaks would you make to [change x] to help you and your team?
What are you and you team’s biggest concerns about [change y]?
I’m thinking about making [change z], how long would it take to privately solicit feedback from your team on it?

Do you find it easy to communicate with me?
What’s one thing I could do to make things easier for you and your team to keep me informed?
What do I just not understand about you or your team that if I did, things would be better?
How often do you think is the right frequency for us to get on the same page?
How would you prefer to update me? (Work with them to adapt this to fit your needs)
What do you think is fair for me to expect from you?
What do you think is fair for you to expect from me?