7 most difficult interview questions and how to answer them – question 5

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Have you ever had a boss who you found difficult to work with?

Many of us have had a manager or supervisor who we have struggled, for one reason or another, to work with and often welcome the opportunity to moan about them but this is not the time to do that.

Your answer to, “Have you ever had a boss who you found difficult to work with?”  paints a clear picture about you and what you are like to work with.


This is not the time to start bad mouthing a previous boss and saying what a poor manager he/she was; nor is it the time to highlight any areas where a previous boss said you fell short as this will immediately start the warning bells ringing in the interviewers mind.

This question is one that you have to answer very carefully even if you have legitimate reasons for finding a previous boss difficult to work with. Rather than highlighting where the difficulties arose, you would be better saying that you can get on and adapt to work with anyone and that because everyone is so different, there is always something to learn from different management styles.

Another approach is to talk positively about an incident where you didn’t agree with a previous boss and how you encouraged an open discussion on the subject which allowed you to get a clearer understanding of his position and his expectations. Then go on to say how this was a good learning experience for you and how you believe that good communication is essential to ensuring good working relationships and the success of a project.

Using one of the above approaches to answer this question will ensure that you do not say anything negative about yourself or about a previous boss. Instead you will have highlighted how it was the situation, not the person that was difficult and shown how you took proactive steps to resolve the situation.

If you have an interview coming up and would like help preparing for it, please contact us .

Related articles:

Question 1  – What achievement in your life are you most proud of?

Question 2 – Why are you interested in this job?

Question 3 – What are the biggest strengths you would bring to this Job?

Question 4 – What are your weaknesses?






I am a Certified Advanced Resume Writer, Employment Interview Consultant, and Career Coach and it is my aim to help ambitious and motivated people like you become fully empowered to get the job you want.