Forming Values 

  1. How do you perceive your early background/family experience to have impacted your career? 
  2. How has your personal background (upbringing, schooling) influenced what you are today, your career progression, and your management/people style? 
  3. What are the values you are taught in your family? 

Professional Relationships 

  1. Where do you relate the best?  Up one level, down one level or with peers? 
  2. How are you best managed? 
  3. How do you build a team under you? 
  4. What qualities have you liked/disliked in your bosses – why? 
  5. How do you evaluate the performance of your subordinates?
  6. How do you elevate a subordinate’s performance? 
  7. How do you show your anger and frustration?  (The value of these questions is as much in how the candidate answers them as what he/she says.) 

Priorities and a Balanced Life 

  1. Discuss the importance of your job vis-à-vis your family and your faith. 
  2. How do you balance your personal and business lives? 
  3. How do you reward yourself for working hard?  How would you spend more free time if you had it? 

Career Success 

  1. If I hadn’t contacted you about this search, what would have been your current career prospects in your current company?
  2. Tell me about your most recent interview. 
  3. According to your definition of success, how successful have you been? 
  4. Do you consider yourself lucky? 

Handling the Downside 

  1. When and why have you fired people? 
  2. Have you made any mistakes during your career?  If so, what were they?  How did you fix them? 
  3. Let’s talk about “set-backs.”  How have they affected you and your family? 
  4. Is there any pattern to critical feedback you tend to get from others? 
  5. What is the most adverse situation with which you have had to deal in your personal or professional life?  How did you deal with it?  What was the outcome? 
  6. Tell me about the events surrounding firing someone or severely reprimanding someone.   

Nowhere to Hide 

  1. If you were speaking tonight at the National Association of Manufacturers or the American Hospital Association, which subject would you select that would enable the audience to see what is special about you as a businessperson? 
  2. What was the most difficult ethical decision you have had to make and what was the outcome? 
  3. What is the difference between a good position and an excellent one? 
  4. Tell me how your approach to managing an organization has changed from the way it was 10 years ago. 

Another way to group questions 

  1. Problem
    Tell me how you have reacted when you see a boss proposition a subordinate? 
  2. Continuum
    Where do you see yourself on a continuum between growing people vs. getting the job done? 
  3. Comparison
    How do you compare and contrast improving results through a salary reduction vs. reducing staff? 
  4. Future Assessment
    If we hired you next week, what unfinished business would you leave in your current work?

Adapted from Executive Recruiter News.