Tough Interview Questions

To help you prepare for your next job interview, here are 30 of our hardest interview questions.

Tough was written by and updated on December 5th, 2020. Learn more here.

Question 2 of 30

Have you ever experienced conflict with a boss or professor? How was it resolved?

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How to Answer: Have you ever experienced conflict with a boss or professor? How was it resolved?

  1. 2.

    Have you ever experienced conflict with a boss or professor? How was it resolved?

      How to Answer

      Employers want to know that you are respectful of your leaders. While you do not always have to agree with your leader, the interviewer wants to see that you respond to them with kindness and respect.

      Talk about a time when your boss made a choice to which you did not agree. Explain how you responded. The key to successfully answering this question is to impress upon the interviewer that you are a respectful employee who treats others with dignity and kindness. If you are newer to your career, you can draw from a post-secondary example (Perhaps you had a conflict with a professor).

      Rachelle's Answer

      "I had a conflict with a manager earlier in my career. One of our team members skipped out on work six times in one month, and I was always asked to cover their shift last minute. I was frustrated and could not understand why my manager wasn't just terminating the employee. I reacted hastily, and the manager patiently reminded me that he had his reasons. He explained that he asked me to cover the shifts because he liked me and I was reliable. It turns out the absent employee had serious health concerns, and our manager was trying to be empathetic without disclosing the situation to our team. I felt terrible and learned that sometimes things aren't always as they seem. I apologized, and all was well."

      Rachelle's Answer for an Admin Interview

      "There are times when I have asked questions or brought up suggestions that challenged a boss or coworker. We resolved the matter with humility and the intent to resolve the problem while better understanding the opposing viewpoint."

      Rachelle's Answer for a Manager Interview

      "One of my first bosses was very hard to get along with as his expectations were often unreasonable and would come with little explanation. I stayed with him for about two years and left when I knew I was no longer benefitting from his leadership. I did keep my head down for the most part, but the benefit came to me at a later time, when I took on my first management role. I knew what I did not want to be like and thus, the experience helped to shape my management style."

      Rachelle's Answer for a Marketing Interview

      "I had a boss that was incredibly skilled at his job but was overly direct. He led with tough love, and while that worked for him and some people, it did not go well with the graphic designer on our team. I tried to stick up for her and let him know that while his heart was in the right place, his approach wasn't effective and was hurting her productivity. At first, it was a conflict because he felt insulted that I was questioning his management, but finally, we were able to come to an understanding, and he considered a new approach for her and the employees in general. I was happy that I stood up for her in a tactful way and the department was better off as a result."

      Rachelle's Answer for a Retail Interview

      "One of my first mentors shared with me a nugget of knowledge: if you're comfortable, you're not growing. So, I try to seek out opportunities for small discomfort whenever possible. I keep a running list of things that I have identified as areas for improvement in the department and bring them up tactfully with my boss. When I lay out the reasons for the upgrades, she lets me tackle the issue. Occasionally she pulls rank and says no, and though it's frustrating, I know that she must know more than I do, so I bite my tongue and put my head down and get back to work."

      Rachelle's Answer for a Sales Interview

      "I have disagreed on many occasions with professors or bosses, but there have only been a few times where it has come to a head. One instance that comes to mind was regarding the distribution of my accounts when I was transitioning to another role. My boss had a plan that conflicted with the recommendations, which was a problem because I know some of my accounts specifically disliked those account managers. I laid out the reasons why I was upset and frustrated with the decisions he was making. He explained why he was making them, and in the end, we identified three accounts that could be switched around so that everyone was happy and the branch didn't lose any business."

      Rachelle's Answer for a Teacher Interview

      "I have experienced conflict with the student of a parent recently, which was quite unnerving. The parent misunderstood the grade that their child came home with and came down hard on me via email, and then by calling my Principal the following day. I called the parent immediately, asking for a face to face meeting. Once we met in person and I was able to walk the parent through the project, and expectations, they realized their child did indeed breeze over a lot of the work. A face to face meeting made all of the difference in that situation."

      4 Community Answers

      Anonymous interview answers with our interview experts feedback

      Anonymous Answer

      "Last year, I had a conflict with a previous manager. At the time, we had several large projects being worked on at the same time. I requested more workforce to address the large workload but was denied. My team and I completed the projects simultaneously through many hours of overtime and no vacation. After these projects were completed, my feedback was recognized by the manager, and the department gained two new-hires to address high volume workloads. In the end, the conflict was resolved reasonably."

      Lauren's Response

      Good example.


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      Anonymous Answer

      "We had a remote meeting about any concerns we have before returning to the office and I addressed COVID19 as a nice break from active shootings but we need to reinstate "active shooter awareness" training since we get occasional threats from irate clients. I was asked to sign a warning not to mention inappropriate topics; I was told this may scare people from returning to the office. I communicated I personally know survivors and victims of a domestic terror attack and I feel strongly about how reinstating the training can potentially save lives. I gave further details and ended up with an offer to permanently work from home and the training was reinstated. I did not have to sign the warning either."

      Marcie's Response

      This definitely sounds like a tense situation. Perhaps you can think of another example to mention in response to this question that is a little less intense? While your concerns here are 100% valid, the fact that your current employer has asked you to sign a warning and to stay at home, for the time being, might raise red flags for the interviewer.

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      Anonymous Answer

      "In my first job in Canada, it was very difficult to understand the principle of responsibility, and I didn't agree with some decisions from my boss. We have some contradiction opinions, but after a few times, he took the time to explain to me, and I understand."

      Lauren's Response

      I added a bit more depth to your response; I want the interviewer to get a sense that you reflect upon previous experiences to make yourself better as an employee. See my suggestion below.

      "During my first job in Canada, there were several occasions when I did not agree with my boss. To remedy these issues, we discussed our differing opinions, so that we could better understand the thought process behind our ideas and stances. This ultimately helped our working relationship because we better understood our individual work styles. The position helped me grow tremendously as a professional."

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      Anonymous Answer

      "Yes, I sensed a change in the relationship with my senior labour relations employee. So I used his outlook and booked a call with him (he works remotely). I opened by telling him why I was calling and asking him if I had done something to attribute to the change in our relationship. He was surprised. We discussed it. He told me he had a lot of respect for the fact that I set up the call to address what I sensed had changed. And things improved from there."

      Rachelle's Response

      You took the bull by the horns and initiated a potentially uncomfortable conversation. Well done!

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