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Job Interview: Who Was Your Best Boss And Who Was The Worst?

best and worst boss

In a job interview, you can get asked different kinds of questions. It’s important to understand why interviewers ask these questions. Also, you need to make sure that you can answer the most frequently asked job interview questions. Some questions are considered more tricky than others. For instance, the job interview question ‘who was your best boss and who was the worst?’. 


Asking about your best boss and your worst boss gives the interviewer insights into your personality and whether you’re a person that holds grudges. Other ways that the interviewer can ask you this question:

  • Describe your ideal manager/boss
  • Who was the best boss in your career?
  • Who was the worst boss in your career
  • What was your supervisor like to work for?
  • Have you ever had difficulties working with your boss/manager?

Furthermore, check our job interview preparation checklist.

Why is the interviewer asking about your best boss and your worst boss?

The goal of the interviewer is to find the best suitable candidate for a job. Regardless of the position, there are always some skills that make some candidates more favorable than others. For instance, if you present yourself as someone that takes responsibility for your own productivity and as coachable in general, you are more likely to make a positive impression on an interviewer. The interviewer wants to find out if you are the right fit for the company culture, but also if you can take directions from managers, and how you handle authority in general.

Realize that the interviewer is not really interested in the skills or abilities of your boss or how good or bad he or she was. They want to get an idea of your compatibility to the management style of the company and how you deal with difficult bosses.

How to answer job interview questions about previous bosses

When the interviewer asks you this question, it might look like a trick question, but as explained earlier, it’s not. You can take advantage of this opportunity and show your best side when talking about your experiences with different bosses. Even if you have a terrible boss in the past, don’t immediately start rambling about how awful it was to work on his team.

The interviewer is not interested in negativity. If you paint a very negative picture of a previous employer, the interviewer might wonder how you will talk about their organization if you are hired and it does not work out. Therefore, make sure that you focus your answers on how you were still able to stay productive even though you were facing challenges with a manager or boss. If you come across as a complainer or a malcontent, the interviewer will most likely pass on you. Make sure you come across as a professional that puts the success of the company before personal feelings.

Preparing your answer

The first step into preparing your answer is to thoroughly analyze the job description. It’s always a good idea to relate your answers to the requirements of the job you’re applying for. For instance, if the positions you applied for requires advanced financial modeling skills and a manager or boss taught you valuable approaches, you could reference that manager or boss as one of the better ones for that specific reason.

Your goal when answering this question is to stay positive. Creative responses are usually the best way to answer tricky questions such as this. For the interviewer it’s about you; they don’t care about your last boss because they don’t know this person. The interviewer could actually care less if that particular boss was good or bad. They introduce the topic because they’re interested in your attitude towards potential managers or bosses at their company.

The chance of being asked ‘boss’ questions is likely. How you will answer the interviewer’s question can determine whether you are the right person for the job. Therefore, make sure you prepare your answer carefully in advance and come across confident.

Example answers to interview questions about previous bosses

Below some sample answers are given. You can use them as inspiration for your own answers. When an interviewer asks you this question, it’s better to go for safe and not include a horrible boss example.

General answer:

‘Personally, I’ve always been able to get along with my bosses on a professional level. This includes my current boss. Professional settings such as the workplace require from you that you get along with different types of people and personalities. This goes for your co-workers as well as your managers and bosses. In general, sometimes you have to share ideas and be open to input from others, while other times, you just have to agree to disagree. The goal should always be to put the interests of the company ahead of any personal feelings. Whenever you leave a discussion or conversation, it’s important to be focused on your tasks and making sure that the actions you take are done to meet your objectives and goals.’ 

Best boss answer:

‘In my previous job, my boss really helped me develop as a professional which I will always be thankful for. As I gained more experience in my position, he enabled me to take on more responsibilities. After 3 years, he promoted me to the position of team manager and taught me how to acknowledge and recognize the strengths of individual team members. He helped me in the initial years to structure my team and to apply each individual’s strength to the fullest extent. UTothis day, I apply this philosophy of trying to get the best out of people and understanding that everybody has something positive to add to a team effort.’ 

Worst boss answer:

Again, only use this answer when you’re pressed to describe the worst boss you had in your career.

‘I once had a boss that used a very different style of communication. Even though we worked together well and finished our projects on time, the feeling was not the same as with other managers and bosses I had in my career. We were not really able to create a bond, and I sometimes had some trouble understanding what he meant because he was hard to gauge. Due to the communication not being clear at times, we had a rocky start, but that was just because the expectations were not always clear to me. As time past, I got more used to this and could adapt to the situation. I was able to stay focused and work together on a professional level to complete the needed objectives and tasks.’

Job Interview Topics – Common Job Interview Questions & Answers

Below you can find a list of common job interview topics. Each link will direct you to an article regarding the specific topics that discuss commonly asked interview questions. Furthermore, each article discusses why the interviewer asks these questions and how you answer them!

  1. Accomplishments
  2. Adaptability
  3. Admission
  4. Behavioral
  5. Career Change
  6. Career Goals
  7. Communication
  8. Competency
  9. Conflict Resolution
  10. Creative Thinking
  11. Cultural Fit
  12. Customer Service
  13. Direct
  14. Experience
  15. Government
  16. Graduate
  17. Growth Potential
  18. Honesty & Integrity
  19. Illegal
  20. Inappropriate
  21. Job Satisfaction
  22. Leadership
  23. Management
  24. Entry-Level & No experience
  25. Performance-Based
  26. Personal
  27. Prioritization & Time Management
  28. Problem-solving
  29. Salary
  30. Situational & Scenario-based
  31. Stress Management
  32. Teamwork
  33. Telephone Interview
  34. Tough
  35. Uncomfortable
  36. Work Ethic

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