- What would you like to be remembered for?
- What has been your greatest accomplishment?
- What has brought you the most fulfillment in your life?
- What was the happiest day of your life?
- What do you wish your younger self had known about (success, relationships, being a parent, etc. that you know today?
- Can you tell me something about your own career and how you got to your current position?
- What do you like best about working for your organization?
- In terms of your own effectiveness and how you spend your time, what would you like to do less of, and on which activities do you want to spend more time?
- Tell me about your family. How old are your children?
- When you’re not shaking things up here at work, how do you spend your free time?
- What do you think about (a current event, election results, or something else in news)?
- Who have been influential role models or mentors to you?
- Where did you grow up? What was that like?
- What were your parents like? What did you learn from them?
- If you hadn’t gone into (whatever field they are in), what do you think you would have done instead?
- If you had to write your obituary today, what would it say?
- What’s the most memorable book (movie, concert, etc.) you’ve ever read (seen, been to)?
- Do you think you are an introvert or extravert? Why do you say that?
- In thinking about e-mail, the phone, writing, face-to-face meetings, social media – how would you describe your communication style and preferences?
- Tell me about your early career – what did you do the first five or ten years?
- How did you get your start?