When a hiring manager asks, “Have you ever had trouble working with a manager?” they just might be fishing for negative answers.

These are the types of interview questions that you should answer with caution.


You don’t want to come across as bitter, negative, or critical during an interview.

More on this as you keep reading to find out how to navigate this cryptic question and come out on top.

Reasons Behind the Question

So, what’s the hiring manager’s motive when asking this question?

It’s not just to make conversation, that’s for sure.

Here are a few underlying questions the interviewer might have:

  1. Are you a good team player?
  2. Do you try to maintain positive work relationships?
  3. Can you remain objective in difficult situations?
  4. Would you be a confrontative employee?
  5. Do you tend to have personality clashes with others, managers included?

So, let’s discuss some things you’ll want to keep in mind as you prepare a positive and well-rounded answer.

Focus on the Sunshine

We would never advise you to lie in an interview.

However, filtering the truth can help in this scenario.

When an interviewer asks about possible negative workplace scenarios, you should always answer in a positive light.

Even if you have had a string of terrible bosses, it would be best to stick to the famous rule stated in the Disney classic, Bambi:

“If you can’t say anything nice, don’t say anything at all.”

Once you start to discuss the negatives, you will appear to be a negative employee, and you definitely don’t want that.

Unfortunately, the interviewer will not side with you on these questions.

If you begin complaining about your previous manager, they will assume that you will also complain about your future manager.

In short, you likely won’t get the job if you come across as negative or petty.

(For more interview questions and answers, see the 50 Top Job Interview Questions And Answers.)

Show Perspective

If you have had managers that you had trouble working with, you don’t have to hide it completely.

There is one great way to answer this question honestly if you feel inclined to share a story about having trouble working with a manager:

  • Give an example of a situation that did not affect you directly.
  • This way, you will automatically speak with more objectivity.

For instance, you can speak of how the manager was overworked and stressed.

This will help you to come across as concerned and reasonable.

It also shows that you didn’t have problems with the supervisor. 

Instead, there were outside factors involved.

Ignorance Is Bliss

Now of course, if you have had a series of great bosses, you can tell the truth.

(You can also consider yourself lucky!) 

Use those great experiences to express how you have received positive motivation from your former employers.

You can always feel confident expounding on a positive response, even to a negative interview question.

Just make sure you don’t go overboard to where your answer seems unrealistic.

After all, no one has perfect working relationships across the board.

Make It Relatable

Any chance you get, relate your skills and experiences to the requirements of the position you are applying for.

Mention positive traits or relevant skills you used to help bring a positive resolution to the issue at hand.

This will ensure that you will leave a positive and lasting impression!

Determine how this question can provide you with the opportunity to relate your experience with the job description.

For instance, you can provide an example of how a trying situation with a former manager pushed you to grow as a professional in your industry.

  • Convey the ways that working through the difficulty have helped you.
  • Remark on how it has helped you improve your working relationships since that time.
  • Also, explain any practical resolution skills you learned through the process.

A Few Things to Avoid

There are a few things you should steer away from in your response.

  1. Don’t share a story if it ended with you losing your job.
  2. Don’t mention it if you and your manager could not resolve the issue.
  3. Avoid talking about a problem as if it is ongoing or happened frequently.
  4. Avoid talking about circumstances in which you were the party at fault.

Sample Answers

Here’s an example that shows a positive perspective from a lucky employee with no “terrible boss” stories to tell:

Hiring manager:  “Have you ever had trouble working with a manager?”

Applicant: “I have been lucky enough to have a string of great employers. Each has pushed me to become a better professional while sharpening my skills in this industry.

I can remember specifically when Mr. XYZ was mentoring me as I was struggling with making cold calls. He didn’t let me off the hook and gave me some great tips.

Now I am one of the most efficient people I know with turning cold calls into long-term clients.”

Following is an example of the applicant explaining a difficult scenario, but keeping themselves from being in the middle of the situation: 

Hiring manager:  “Have you ever had trouble working with a manager?”

Applicant: “I once had a supervisor that had a lot going on outside of work. She was struggling to balance these issues with her day-to-day responsibilities. This began to play a role in the company morale and was discussed amongst other employees fairly often.

This manager was a great person and was qualified for the position once these issues cleared up. Personally, I did not have a problem working with her as we always had a great professional relationship.”

Closing Thoughts

All the best in acing your next interview!

Here at Find My Profession, we would love to help you land the perfect career.

Simply tell us about your previous experience and we will do the research on where your skills could be best applied.

We offer resume writing services, as well as career coaching packages.

Get in touch today and let us help you navigate your job search.