​Interviewing people for jobs can very difficult, especially for leadership or management positions. You often have only a limited time available to ask questions, and many candidates are so well prepared it can be difficult to get beneath the polished veneer that they are looking to present, and find out who they really are. Technical ability is fairly easy to assess but it's their soft skills, their emotional intelligence that is going to have a much bigger impact on whether they will be successful or not.

You need to get them talking about themselves freely, throw them out of their rhythm, and try to find out who is the person behind the mask, The better you can do that, the more successful you will be in your hiring.

Here are 40 interview questions that I have used when interviewing for leadership positions, which have helped me identify the best candidate.

As many of these are open-ended questions give your candidate as much time as they need to answer them, the more they speak the more they will reveal about themselves.

  1. What value do you bring to this organization?
  2. If you could start your career over again, what would you do differently?
  3. Describe the best boss you ever reported to, and why?
  4. Describe the worst boss that you ever reported to, and why?
  5. Tell me about the biggest failure you were involved in and what you learned from it.
  6. Describe what you think this role is about and why it is important to our company?
  7. Tell me about a project where you did more with less, and how you achieved it?
  8. What does accountability mean to you?
  9. Tell me about a time you had to let an employee go? How did you handle that process, and did it go smoothly?
  10. How do you give people feedback when their performance is not up to standard?
  11. If you could know three things about your boss what would they be?
  12. What's the best feedback you have ever been given, and why?
  13. What's the worst feedback you have even been given, why, and how did you handle it?
  14. If you were asked to do something that was impossible, how would you handle that?
  15. We asked your previous bosses what they liked and disliked the most about you, what do you think he said?
  16. What kind of challenges would you not want to be involved in?
  17. What's your biggest fear in life?
  18. What would you do if you won the lottery?
  19. If you could go back an redo your college years, what subject would you study, and why?
  20. If we asked you partner about you what would they say?
  21. Is the customer always right and please explain your thinking?
  22. What have you done professionally that you succeeded at, but isn't an experience you'd want to repeat?
  23. Is it better to be perfect and a little bit late, or ok and on time?
  24. In less than 5 minutes, please explain something to me that is complex, but you know and understand very well?
  25. What is something you'd be happy doing every single day for the rest of your career?
  26. If you had $1,000,000 to start your own business, what kind of business would you start?
  27. What's the biggest decision you have ever had to make, and how did you go about making it?
  28. What's the toughest interview question you have been asked and what was so tough about it?
  29. If you had to promote one of your staff what skills would you look for in the ideal candidate?
  30. What's the one question you dread most in an interview?
  31. Tell me about a time where you coached someone through a difficult challenge.
  32. What qualities in your co-workers bother you most?
  33. What qualities in your co-workers do you appreciate most?
  34. Tell me about a work incident in which you were totally honest, despite a potential risk or downside for yourself.
  35. What your favorite Leadership/Management book and why?
  36. How do you handle it when co-workers or your team challenge your decisions?
  37. Describe a time when you were asked to do something you weren't trained or experienced to do. How did you handle it?
  38. Describe a time when an employee was underperforming, how did you handle that situation.
  39. In 2 years time, what achievements of yours are we celebrating?
  40. What questions about the job or company would you like answered?