Executive Interview Thought Starter 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.

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?