Private Interview Questions

None of the below questions are required, and we may not get to all of them, but they should provide you with conversation starters as you prepare for our interview.


  • Tell me about your mother and father.
  • What was it like growing up in your home?
  • What is a story you remember clearly from your youth changed you in an important way?
  • How is the world different today than in your youth?
  • When did you know what you wanted to be when you grew up? What influenced that decision.
  • Who did you admire?


  • Tell me about your wife, what makes her special?
  • What did you learn about yourself by being married to your husband?
  • When did you know that this person was a good choice as a spouse?
  • What should your children know about marriage?


  • What did you learn by becoming a parent?
  • What do you hope your children remember about their childhood?
  • What were some hard decisions you had to make as a parent?
  • What should your children know about work? family? god?


  • Why did you work as hard as you did?
  • How did you handle stress, what did you learn from that?
  • What did you sacrifice to provide for your family?
  • What choices are you glad you made?
  • What is success in your eyes?


  • How do you want people to remember you?
  • How should your friends and family pay their respects after your passing?
  • What do you want to live on from what you accomplished?
  • What life lesson was the most difficult to learn, but was the most valuable to know?

Start-up phase 

  • How did the business get started?
  • Where did the initial funding come from? 
  • Did anyone try to talk you out of starting this business?
  • Who supported your business?
  • At what point did you start to feel confident that the business could succeed?
    Who were your first employees?

Growth phase

  • Describe a pivotal decision that changed the future for your company.
  • What was a major investment that was difficult to decide to do?
  • Which employees were critical to the success of the business?
  • Was there a time when you had to unwind some decisions that didn’t work out?


  • What characteristics were important when making hiring decisions?
  • What did your employees like about working for you?
  • What did you do to celebrate individuals that were strong contributors?
  • What do you hope your employees say about your business? 


  • Did anyone ever steal from you? 
  • What historic/economic pressures forced you to make tough decisions? 
  • Do you have regrets about your career? What vices did you lean on? 
  • Did you ever have to let someone go that was particularly difficult/painful?


  • What did your business create that you are particularly proud of?
  • Who was your mentor as you led this organization? What did they teach you?
  • What do you want to live on from what you and your business accomplished?
  • What should the next owner of your company remember as they are making decisions?