Being a manager in new organization can be a challenge, especially when there are generation and experience gaps to bridge. I've put together the following list of questions that I ask all of my directs to get an idea of who they are, and where they're headed, and most importantly, what their expectations are!

Please add to this list via comments if you've had similar experiences or have additional ideas/questions!

1. How long have you been with the company?
   
2. What does a day in the life of your job look like?
   
3. What do you like most about what you do?
   
4. What keeps you here?
   
5. Generally, what are you looking for in a leader (manager)?
   a. What are your expectations of me, as your leader (manager)?
   
6. Has anything changed about the management structure here?
   a. What was the former management structure prior to my arrival?
   b. What did you like/dislike about it?
   
7. What frustrates you at work? Give me an example of a particular incident.
   
8. What other departments have you worked in at this organization?
   
9. Part of my role here, as your leader, is to do what I can to set you up for success. Is there anything (within reason) that I can do for you right now?
   
10. I noticed that from your last IDP (individual development plan) you were going to be working more on __________. How is that coming along?