Here’s a few one on one meeting questions to ask to get you started:

• 1) How are you? How is life outside of work?
• 2) How do you feel your work/life balance is right now?
• 3) What is your resentment? (A great lesson from Marissa Mayer)
• 4) What’s one thing we could change about work for you that would improve your personal life?
• 5) If around a holiday: Do you celebrate [Holiday]? How was it?
• 6) How are your parents/grandparents? Where do they live? Do you visit them?
• 7) If they have children: How is [name of child] doing? (Ask something related to their age like starting school, playing sports, or other interests.)
• 8) What do you like to do in your free time? What are your hobbies?
• 9) What did you do for fun in the past that you haven’t had as much time for lately?
• 10) What drives you? What motivates you to come to work each day?

Start by establishing their goals.

• 11) What work are you doing here that you feel is most in line with your long term goals?
• 12) As a kid, what did you want to be when you grew up?
• 13) What do you want to be doing in 5 years? 10 years? 3 years?
• 14) What are your long term goals? Have you thought about them?
• 15) Who do you really admire? Why? (People often admire those they want to become)
• 16) If you had millions of dollars, what would you do every day?
• 17) What are your super powers? What powers would you like to develop?
• 18) What do you want to do in your next job?