Challenging Executive Interview Questions:

By July 20, 2019 March 15th, 2020 18 Comments

Executive candidates are expected to frame their successes in metrics. Revenues, shareholder value, gross and net profits, stakeholder relations, growth strategies, industry and company ranking, restructuring, and leading teams are typical measures that showcase success in quantifiable terms. You will be provided with ample opportunity to exhibit your level of influence, temperament, resiliency, and innovation in the interviews that will be conducted.


Here are some interview questions that executives should prepare for…


Common Questions:

  • What is your greatest professional achievement?
  • Why are you interested in leading the company?
  • What would leading this company mean to you?
  • How would you describe your leadership style?
  • How do you prefer to communicate?
  • How would you measure success in this role?
  • What traits does a good manager need to succeed?
  • What aspects of this position would you struggle with?
  • How do you boost staff morale?
  • Tell me about a time you dealt with challenging staffing issues. How did you handle it? What were the outcomes?
  • What do you think the company is doing well? What would you change?
  • If hired, what would your priorities be within the first six months?
  • Have you ever had to terminate an employee? How did you handle it?
  • Tell me about a time when you faced difficult financial issues? What did you do?
  • What do you do when an employee comes to you with a complaint?
  • Tell me about a time when you disagreed with other executives. What did you do?
  • Tell me about a time you experienced resistance to one of your ideas or projects.
  • Tell me about a past goal or deadline that you missed.
  • What challenges do you foresee for the next person in this role?
  • What critical feedback have you most often received from your superiors?
  • Tell me about a contentious situation between colleagues you’ve had to resolve. Specifically, how did you work through the tension?
  • What comes to mind when you’re dealing with challenging staffing or financial issues?


Challenging Questions:

  • Who is your mentor(s), and what recent challenges have you sought their advice for?
  • Tell me about a time when you had to make a tough business decision that supported your company’s purpose, but may have had a negative, short-term financial impact.
  • Tell me about a time you broke a rule for an employee.
  • What are you learning right now?
  • Can you successfully deal with under performing employees?
  • What is one truth you believe in that most people disagree with you on?
  • What’s one assumption people make about you that is dead wrong?
  • Tell me 3 things about you that are not on your CV.
  • What is most challenging about being an executive?
  • What would be your approach to boosting staff morale and sales after a merger?
  • In the past, how have you evaluated an employee’s job performance? Do you think this is still an effective way to evaluate performance?
  • Tell me about a time when you had to confront an employee who was producing inadequate results? What did you do?
  • What is your experience in reading and interpreting financial reports?
  • How would you handle shaky sales after a merger (or another big event)?
  • Tell me about a time when you promoted teamwork and strengthened inclusion in the workplace.
  • What is something you don’t want me to know about you professionally?
  • When do you know you have delivered something outstanding?
  • What should we associate with your name?
  • What will your employees learn from you?



Levi Swartz is a Professional Career Coach and a former Executive Search Consultant. He opened his practice to make a difference in the job market for candidates who struggle to find success in this challenging climate. Levi serves all professionals from various industries and tenure. To schedule your free consultation, feel free to call 509-944-0494, or e-mail him directly at: levi@risehighcareercoaching.com  


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