101 Questions to Ask in One on Ones by Jason Evanish (external link to his blog). Questions to deepen your understanding and effectiveness, broken down by categories.

Preview:

Questions to talk about Short Term Goals

Short term goals are things to be done in the current quarter or month. They’re high level projects assigned to that person.

1) How is [project] going? What could we do to make it better?
2) Is there anything blocking you from getting your work done?
3) Are there any projects you’d really like to work on if you were given the opportunity?
4) What parts of your job would you like to deepen your skills in or get additional training in?
5) Is any part of your project unclear or confusing?

These are all about getting feedback so you can improve their day to day and relieve frustrations on their projects. You already spend a lot of time on their day to day job in standups, status reports, etc so this is intentionally a short set of questions relative to other areas you spend a lot less time talking about usually.

Questions to talk about Long Term Goals

Long term goals are all about who they want to become. Everyone is growing in different ways and people are happiest when they feel like they’re making progress on their big life goals. These questions will help you learn what those goals are and see if they feel they’re making progress on them.

6) What do you want to be doing in 5 years? 10 years? 3 years?
7) What are your long term goals? Have you thought about them?
8) Do you feel like you’re making progress on your big goals here? Why or why not?
9) What’s one thing we could do today to help you with your long term goals?
10) Do you feel we’re helping you advance your career at a pace you would like?
11) Who do you really admire? Why? (People often admire those they want to become)
12) If you had millions of dollars, what would you do every day?
13) What are your super powers? What powers would you like to develop?
14) What are your big dreams in life? Are you making progress on them?
15) Could you see yourself making progress on more of your goals here? What would need to change to do so?
16) What work are you doing here that you feel is most in line with your long term goals?
17) As a kid, what did you want to be when you grew up?

These questions will help you make sure your people are progressing in the areas that matter most to them. Realize they will change over time, and it takes time for people to really open up about their dreams, so it helps to revisit them regularly.