When we discuss entrepreneurial success, we talk about the power of failure, the impact of smart time-management, and the importance of networking. But none of this matters if you don't have the right team by your side.

Hiring the right people (the right skill sets with the right cultural fit for the right role) is arguably the hardest job any entrepreneur has.

Every time we interview someone, we mainly have five goals in mind. We want to:

  • Reveal personality behind the resume
  • Understand if the candidate is a cultural fit
  • Uncover candidate's aspirations and motivations
  • See how well (s)he does under the pressure
  • Discover if a candidate is a (potential) innovator and/or good leader

To truly unearth someone's character, you might want to look beyond conventional interview questions.

Below are some of my favorite examples of questions I have been asked (and asked myself) throughout the years that helped bring forth interviewees' personalities, qualities, and aspirations.

  1. What's your favorite joke?
  2. If you were a brand, what would be your tagline?
  3. What's your superpower?
  4. What was your favorite Halloween costume and when have you worn one last?
  5. What would you do in the event of zombie apocalypse?
  6. What do you envision your life to be in 5 years?
  7. Tell me one thing you and your friends most disagree on.
  8. What is the toughest decision you have ever had to make?
  9. If you get a chance to be a CEO of our company for a day, what is the one thing you would change immediately?
  10. What is the one book you would recommend everyone reads?
  11. If you get a chance to start a business, what would it be? Why?
  12. Who is the smartest person you know? Why?
  13. Pitch our company to me as if I were buying your product/service.
  14. What advice would you give your previous boss?
  15. Teach me something I don't know in the next 5 minutes
  16. Do you have passion projects outside of work? What are they?
  17. What is the one thing I would never guess about you from your resume?
  18. What do you usually do when you find that you lost all track of time?
  19. A talking donkey walks in this room wearing a cowboy hat. What does it say?
  20. Are you a lucky person? Why?
  21. If you had 10 years to live, what would you do?
  22. What's the best piece of advice you've gotten?
  23. What 2-3 things you need to be successful in this role? What are the deal-breakers for you?
  24. What qualities should a team leader have?
  25. When was the last time you disagreed with your CEO/manager? Did you voice your opinion?
  26. Would you rather be liked or respected?
  27. Name the skill you self-taught yourself.
  28. On the scale of 1 to 10, how weird are you?
  29. You won a $10 million lottery. What would you do?
  30. What's your backup plan if you don't get this job?

Some of the questions are designed to break the ice, some to bring out interviewee's personality, values and aspirations, some to not only see whether she did her homework about your company, but to see if she fits into the company's culture, some to identify if she crumbled under the pressure, and some to uncover both creativity and the leadership traits. None of these questions should throw the right candidate off or confuse him. After all, the right team members will not be afraid of or put off by any challenge in their path. Right?