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. After all, you may have strong feelings about the bosses you've had during your career. 

The important thing is to keep your response to this question positive, even if you worked in a negative environment or are discussing a frustrating, unhelpful manager. 

Here's more information on why interviewers may ask about previous managers, and the best way to response.

What the Interviewer Wants to Know

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 assign blame or carry a grudge. 

Your response also reveals a lot about you, from the kind of supervision you prefer to your style as an employee. Employers look for staff who are coachable, responsive to management directives, and take responsibility for their own productivity. 

They also want to determine whether you are a match for the culture of the company. For instance, if a company has a hands-off management style, and you call that out as a negative aspect of a previous supervisor, it could indicate that you're not an ideal fit for the company at hand. 

How to Answer Questions About Bosses

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 your qualifications for the job into 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:

Example Answer

I've learned from each boss I've had. From the good ones, what to do, and from the challenging ones, what not to do.

Why It Works: This response shows that the candidate uses even negative experiences as a learning opportunity. 

Example Answer

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 hands-off management style, but I appreciated the interaction with the first manager I mentioned.

Why It Works: This answer is honest, and shows the candidate's preferred management style. 

Example Answer

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 outfitwithout being pushy, and taught me to increase my selling abilities tremendously.

Why It Works: In this response, the candidate takes advantage of the question to point to a skill learned through a manager. This is a particularly strong answer if the candidate is applying to a sales role, where know-how about suggestive selling will be helpful. 

Example Answer

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.

Why It Works: This answer is honest about a negative experience without being heated. Best of all, the candidate is able to show how they were able to fix the issue, and get the necessary feedback. 

More Strong Answers: 

  • I learned a lot about organizationfrom 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 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 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 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. 

Tips for Giving the Best Answer

  • Talk strengths:When you discuss a "best boss" you can highlight the person's skills. 
  • Consider referencing skills:If a manager taught you a skill — particularly one that's relevant to the role at hand — you can mention that as one of the positive aspects. 
  • Stay positive:Even with a bad boss, keep your tone positive. Don't get personal or gossipy. Try to describe how the manager helped you realize something about yourself (e.g., a particular work environment you crave) or how you were able to convey to the manager what you needed from the relationship. 

What Not to Say 

  • Avoid going negative: This isn't a moment to air your grievances. So, even if you're talking about a bad boss, keep the negativity low. Talk about what didn't work for you without getting personal. 
  • Don't criticize: The reason you don't want to name namesand be specific in your criticism is that it may make your interviewer wonder what you'll say about the company when you've left. And, in some industries, your interviewer may know your previous managers. Keep it discrete! 

Possible Follow-Up Questions

  • What is your favorite position you've held, and why? 
  • What's your least favorite job, and why? 
  • What do you expect from a manager? 
  • How would your colleagues describe your personality? — Best Answers
  • What are your strengths? What are your weaknesses? — Best Answers

Key Takeaways

BE POSITIVE. Don't gripe or complain, even when you're discussing bad bosses. 

SHARE PREFERRED MANAGEMENT STYLE. This is a good opportunity to describe the kind of management style you like, and find out if it's a match for the company's culture. 

TALK SKILLS. If you've learned skills or tactics from previous managers, now is a good time to mention it.