80 Smart Interview Questions from 50 Great Leaders

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By Mike DuBose and Blake DuBose

New employees represent not only a huge investment of time and money, but they can also significantly add to or detract from an organization’s culture. Each time you hire someone, you’re committing yourself and your staff to spending a large chunk of your week with that person. You simply can’t afford to introduce a “rotten apple” or a “slacker” into the mix, and if you do slip up, getting rid of them can be time-consuming and stressful!

When seeking new employees, you must have a crystal clear idea of what you need from them. As DeeDee Doke writes in Interviewing People, “Developing a precise person specification requires an in-depth understanding of the competencies, knowledge, skills, experience, education, aptitudes, and attitudes that the best possible selected hire for this role could have.” You should start with a thorough, detailed job description when preparing to hire for any new position. Looking at the position’s responsibilities, make a list of the traits a person will need to succeed in that role.

Even if a potential employee is perfectly competent at the basic job requirements, there’s another element they must have: culture fit. Only when both of these criteria are met can a new employee truly thrive in a workplace. As Jacquelyn Smith noted in a 2012 Forbes article, employers don’t hire resumes, but “the whole person: their personality, their resume, their critical thinking and creative ability.” Therefore, add to your list any attributes valued by your organizational culture that the applicant should display. (These may vary depending on the type of position or environment—for example, a quiet, introverted individual may perform well in accounting, but an extroverted, outgoing person would be needed for sales or marketing.) Doke suggested that interviewers break down their requirements into “essential” and “desirable” categories to help determine the short list of candidates. From there, it’s a matter of zeroing in on people who possess these qualities using insightful, legal questions.

What you’re looking for will be different for every interview. It depends on the culture of the organization and the requirements of the particular job. For example, a startup’s number one priority may be passion—a deep, powerful belief in the company and what it does—which will be necessary to deal with the long hours that will sometimes be required. Likewise, a laid-back, creative individual who takes time to explore all the options may not fit in as well in some results-oriented corporate environments. No personality is “wrong;” but some people may be a poor fit for the job or the culture—and it’s the interviewer’s responsibility to determine who is and who isn’t.

Many candidates will try to say what you want to hear, so it can be hard to tell who is genuine and who is just trying to snag a job. That’s why the best interviewers put interviewees at ease first by bonding with them and making them feel comfortable. Then, they sit back, probe with the right questions, and let the potential employee drive the conversation. Ideally, the job candidate should talk the majority of the time (roughly 80%), while the interviewer listens, watching for warning signs that that person won’t be right for the job.

We have a very thorough employment process at our companies that, although time-consuming, has greatly assisted us in finding and hiring the right staff. First, we collect resumes and screen the most promising candidates via telephone to find our finalists. We require the finalists to complete online personality and work assessments to pinpoint strengths and areas of concern, and we often use the results of these tests to formulate or target interview questions. From there, we follow the “rule of three,” interviewing the individual on three different days by three different people. (When following this strategy, each interviewer should create their questions in advance and coordinate with the others so there is no overlap.) Be prepared to spend at least an hour on each interview. Once they are complete, meet as a team to compare notes.

We have studied profiles of more than 50 CEOs that were published in the New York Times and the Wall Street Journal over the past two years. The leaders described questions that they ask potential interviewees, and we were impressed by how deeply and cleverly they explored different issues. We compiled, combined, and adapted some of these questions for our family of companies’ use in the future, and we believe that others will find them valuable as well. Try using some of the following questions in your next interview to gain insight on the topics most important to your organization.

Personal history: A person’s past shapes their future. You can learn a lot about how someone overcomes challenges by the way they’ve faced difficulties in the past, and you can understand their level of self-awareness by how they define themselves.

  1. Briefly describe your life from birth until now. What were some high and low points?
  2. What core lessons have you learned throughout life?
  3. Why did you choose your college and major?
  4. Tell me about your summers while you were in college.
  5. What was your career vision when you first started out?
  6. Describe yourself in three words. Why those three?
  7. What have been some of the struggles, conflicts, or frustrations in your personal life?
  8. What’s the hardestchallenge you’ve faced, and how did you overcome it?
  9. Tell me about a crucible moment in your life and how it turned out.
  10. What’s the biggest risk you’ve taken, and what did you learn from it?
  11. Tell me about a time that your trust was betrayed. How did you react?
  12. When was the first time in your life when you realized that you had the power to change or to do something meaningful?
  13. When someone wrongs you, how do you handle it?

Values: What is important to a person in life tells you a lot about his or her personality. Does the applicant glory in recognition, or seek to help causes from behind the scenes? Is he or she passionate about obtaining financial security, supporting an idea, or learning certain skills? All of these traits reflect on how the person will behave in a work environment.

  1. What have been your most rewarding achievements in life? How did you accomplish them?
  2. Describe your passions.
  3. What does your future look like?
  4. Have you considered taking additional college or graduate courses or obtaining other degrees?
  5. How do you spend your spare time?
  6. What is the biggest joy in your life?
  7. Who’s the most important person in your life, and why?
  8. What brings you displeasure?
  9. Besides this job, what are you really good at doing?
  10. If money, time, and talent were no object, what would you be?
  11. Tell me about a movie or book that influenced you and why.
  12. What books, magazines, blogs, websites, and newspapers do you read?
  13. Who has inspired you the most? Why?
  14. What are your top five values?
  15. Tell me something interesting about yourself that isn’t on your resume.
  16. If you could go back in time, what would you do differently?
  17. What do you really want out of life?

Effort: Unlike most of the other topics, there are right and wrong answers for these questions, which are designed to determine how much effort the interviewee invested in preparing for the interview. If they haven’t taken the time to learn about the organization and the requirements of the job they’re applying for (not to mention the values that the company holds dear), they’re probably not the right person for the position.

  1. Describe the job for which you are interviewing.
  2. Tell me what you know about our organization and its culture.
  3. How did you learn about this position and our business?
  4. What questions do you have about the job and our company?

Work habits and personality: These questions hint not only at how well a person has achieved in the past, but also about his or her personality and how it will mesh with the organizational culture. A person who goes on at length about their dislikes in a previous position but doesn’t have anything positive to say won’t fit in with a culture where the glass is always half full. They also shed light on the person’s expectations for the position.

  1. Why do you desire to work for our company?
  2. Where do you think you can add the most value in our organization?
  3. What sets you apart from other applicants for this position?
  4. How would this position fit into your long-term career plan?
  5. What motivated each of your job changes?
  6. Why do you want to leave your current job?
  7. Walk me through a typical day in your most recent job role, including specific responsibilities.
  8. Describe your ideal work environment.
  9. List a few things you liked and disliked about your previous jobs.
  10. What were three instances in your career in which you were the happiest, most successful, and most fulfilled?
  11. What was your favorite job and why?
  12. How would your former employers describe you?
  13. What would your past employers or colleagues change about you?
  14. Who were your best and worst supervisors, and what were their characteristics?
  15. How would you define great leadership?
  16. Have you ever had to fire anyone? If so, how did you do that? (For leaders or managers) Have you witnessed someone being fired in an organization? How did you feel about them being terminated? (For non-leaders)
  17. Name three traits that you dislike in work colleagues.
  18. If you ran your current company, what would you change?
  19. What is your proudest career accomplishment?
  20. What kind of side projects are you working on?
  21. What part of your resume really stands out to you?
  22. What do you enjoy most about working and what do you enjoy least?
  23. How do you organize your workweek?
  24. Describe the last time in your work life that you were in “flow”…you look at the clock, and suddenly it’s 6 p.m.
  25. What is the hardest you’ve ever worked?
  26. Where do you see yourself in five years? (IMPORTANT!)
  27. Tell me about a time when you were asked to do something you weren’t really comfortable with, and describe where that led you in your career.
  28. How do you like to be evaluated on your work performance?
  29. Have you ever received what you perceived as an unfair feedback at work?

Motivation and self-awareness: The phrase “know thyself” has been around since ancient times, but self-awareness is a skill that many find difficult. However, people who are able to admit their weaknesses and recognize their strengths tend to be great employees because they know their capabilities and often work to improve their faults on their own. Use these questions to measure self-awareness and motivation in potential employees.

  1. What drives you to get out of bed in the morning?
  2. Name the biggest misconception people have about you.
  3. What would your friends say are your greatest personal strengths?
  4. What are three areas of self-improvement that you’re working on?
  5. Give an example of something that caused conflict within you. How did you handle it?
  6. What do you want to learn next?

Problem-solving and intuition: These questions are designed to measure how a person reacts to change and solves problems. Many of the leaders we studied named “ability to adapt to change” as a highly desirable trait in employees, and there are many circumstances in a person’s career where the ability to wisely assess and solve problems will prove invaluable.

  1. Describe a time when another person unexpectedly changed the direction of a project you were working on. How did you react?
  2. Outline some issues you have had with your supervisors and how you handled them.
  3. Describe a situation you faced at work that had a disappointing outcome.
  4. Explain a big change that your organization went through and how you adapted.
  5. Discuss a situation where you had to fix a problem without help from leaders or managers.
  6. Describe a project that you believe really showcased your creativity.
  7. Tell me about a time in your career you came up with a thought, got others on board, and executed it.
  8. Think of a time you received some tough feedback. What changes or improvements did you make in response?
  9. Name the best and the worst decisions you’ve made in your life.
  10. Walk me through a complex problem you solved.
  11. Tell about a time you ignored advice that you should have followed. What happened?

The bottom line: Great organizations are built on great people, and it takes effort and innovative strategies to find the right individuals who best fit your corporate culture. Interviews are the key step toward identifying ideal staff members and weeding out the mismatches. Take the time to create and ask smart, engaging questions that hone in on the qualities you’re looking for in staff members. Then, listen carefully (and watch body language)! A lot of work goes into preparing for and conducting good interviews, but it’s worthwhile when the result is a staff full of smart, happy, and highly engaged team members.

See www.mikedubose.com for additional articles on finding, interviewing, and hiring great employees.

About the Authors: Our corporate and personal purpose is to “create opportunities to improve lives” by sharing our knowledge, experience, success, research, and mistakes.

Blake DuBose graduated from Newberry College’s Schools of Business and Psychology and is president of DuBose Web Group. View our published articles at www.duboseweb.com.

Mike DuBose, a USC graduate, has been in business since 1981, authored The Art of Building a Great Business, and is a field instructor with USC’s graduate school. He is the owner of four debt-free corporations, including Columbia Conference Center, Research Associates, and The Evaluation Group. Visit his nonprofit website www.mikedubose.com for a free copy of his book and other useful articles.

Katie Beck serves as Director of Communications for the DuBose family of companies. She graduated from the USC School of Journalism and Honors College.

© Copyright 2016 by Mike DuBose—All Rights Reserved. You have permission and we encourage you to forward the full article to friends or colleagues and/or distribute it as part of personal or professional use, providing that the authors are credited. However, no part of this article may be altered or published in any other manner without the written consent of the authors. If you would like written approval to post this information on an appropriate website or to publish this information, please contact Katie Beck at Katie@dubosegroup.com and briefly explain how the article will be used; we will respond promptly. Thank you for honoring our hard work!