Job Interview Questions About Your Best and Worst Bosses

Foreman shaking hands with worker in factory
••• Getty Images/Jetta Productions

How should you answer interview questions about your past managers? Depending on the supervisors you've had, some of these questions can be tricky to answer. It's important to keep it as positive as you can, even when you worked in a negative environment.

With the question "Who was your best boss and who was the worst?" the interviewer is trying to discover if you are the type of candidate to assess blame or carry a grudge. Employers look for staff who are coachable, responsive to management directives and who take responsibility for their own productivity. They also want to determine whether you are a match for the culture of the company.

Even if you had a boss who was awful, don't come right out and say so. Interviewers don't want to hear negativity, and they will wonder what you will ultimately say about their organization if you are hired and it doesn't work out. Focus your answers on how you were able to work productively despite management challenges.

As with any interview response, take the opportunity to integrate critical assets for your target job with your responses. For example, if a job requires advanced client prospecting skills and a boss taught you some valuable approaches, you might reference that boss as one of your best for that reason.

Examples of the Best Answers

Review the following sample interview answers to find out the best way to respond. Solid sample answers:

  • I've learned from each boss I've had. From the good ones; what to do, from the challenging ones; what not to do.
  • Early in my career, I had a mentor who helped me a great deal, and we still stay in touch. I've honestly learned something from each boss I've had.
  • My best boss was a manager who enabled me to take on more responsibility as I progressed in my job. I've had other bosses with a more a hands-off management style, but I appreciated the interaction with the first manager I mentioned.
  • My best boss was a woman who showed me the importance of suggestive selling. She was able to show a customer the perfect accessories to go with an outfit, without being pushy, and taught me to increase my selling abilities tremendously.
  • I learned a lot about organization from my last boss. I've always been an organized person, but I learned from him new ways to organize and mobilize the staff, which was very valuable to improving my management abilities.
  • My best boss was one who was able to recognize the strengths in his employees and to apply them to their fullest extent. He taught me to look at people more individually and to understand that almost everyone has something positive to offer.
  • My best boss was a person who set such a wonderful example for her employees that she inspired people to work harder. She was always 'up', even when she wasn't, and never let a customer leave unhappy. She would always have the right thing to say to provide encouragement to her customers and employees alike.
  • My worst boss was a man who provided very little feedback about my performance. I was able to improve communication by providing unsolicited weekly status reports on my projects. Eventually, he furnished some feedback and constructive criticism to these reports and I knew better where I stood.
  • My best boss was a woman who taught me more about how to use analytics to frame my business development strategies for clients in my territory.
  • My favorite boss was a very dynamic speaker. She took me under her wing, taught me how to command a room and helped me to become a very effective presenter. 

Prepare for Similar Questions

Also be prepared to answer similar questions about the jobs you've held. The interviewer may ask you which position was your favorite, and which was your least favorite, and why.

When you discuss your favorite job, be sure to reference parts of the job requirements that are a match for the job for which you're interviewing. When you talk about your least favorite position, don't mention one that's similar to the job you're hoping to get hired for.