Tough Interview Questions

30 Questions and Answers by

Rachelle Enns is an interview coach and job search expert. She works with candidates to perform their best in employment, medical, and post-secondary admission interviews.

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

Question 1 of 30

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

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Tough Interview Questions & Answers

  1. 1.

    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."

      Rachelle's Answer for a Bank Compliance Officer Interview

      "I once worked with a supervisor who did not provide any timeline for the projects he assigned to me, yet became extremely agitated when I did not deliver within a few hours. As I had no idea he had such timelines in mind, I requested a meeting with him to tell him about my concerns and that I can absolutely adjust to tight deadlines, however I require prior adequate notice so that I can organize my days accordingly and delegate other duties if necessary. I also told him I cannot anticipate he would want something done right away upon receipt. He told me he did not realize he had provided unclear instructions and promised to be more clear in the future, which he were."

      Rachelle's Answer for a Zookeeper Interview

      "My most recent supervisor and I had a strong work relationship and she will be willing to give you a strong reference on my behalf. We did not run into any difficulty while working together."

      Sue's Answer for an Architectural Drafter Interview

      "When I started working for my past supervisor, he gave me less feedback than I was used to in past positions, which made it hard for me to meet his expectations. We had a few disagreements because each of us misunderstood what the other one wanted. I asked to meet with him to discuss better ways to communicate and asked for more specific, honest input. Once we were on the same page, we worked together successfully for two additional years. When I begin working with a new manager, I now take time to discuss our styles and expectations."

      Heather's Answer for an Autopsy Assistant Interview

      "In my career, I have had many different supervisors with different leadership styles. I did have one supervisor in the past that was new to being a supervisor. We may not have seen see eye to eye on everything but because of those differences we challenged each other and worked really well together."

      Rachelle's Answer for a Medical Transcriptionist Interview

      "When I was in college, someone in my class stole a copy of a final exam before it was given and distributed copies to others in the class. The instructor found out said that, unless the person who stole the test came forward, the whole class would be given an 'F' for their grades. I had been approached by someone with a copy of the test and I privately told the instructor that I knew who had taken the exam. The instructor was kind enough to keep our conversation private and made a new test to be administered. I didn't want to be involved in the frustration of the situation, but I also didn't want innocent students to receive failing grades because of someone else's bad decision."

      Krista's Answer for a Virologist Interview

      "I had a problem with my previous supervisor who would micromanage my research team and me. She was a new supervisor who was hired after my previous manager retired, and she was unfamiliar with how my team and I worked. My responsibility was to supervise my team, and my supervisor's role was to supervise me. She would give tasks to my team without consulting with me first, and it became confusing for my research staff. I asked my supervisor if we could have a meeting, and we met in her office. I calmly explained that my job was to supervise my staff, and her job was to supervise me. I described that it was confusing my research team when she assigned tasks without consulting with me first. She was surprised and unaware of my position and explained how her previous role was to supervise the virologist and the team. My supervisor apologized and said she would assign tasks to me next time. We never had an issue after that."

      Nisha's Answer for an Attendance Clerk Interview

      "I avoid conflicts with my team members as I believe in clear communication whenever any issues are present. There is no reason to have tension in the workplace if you are honest, transparent and an effective communicator."

      Christine's Answer for a Training Specialist Interview

      "As a Training Specialist, I have learned a lot about communication and conflict management through my own career training. It is rare, but I have encountered times when I can't entirely agree with my supervisor. (Situation & Task) While working for Company XYZ as their Training Specialist, one of my leaders was under a lot of pressure to boost the performance of his sales team. The sales department had seen three underperforming business quarters, and now this Sales Director's job was potentially on the line. This Director approached me and requested that I hold a training session focused solely on prospecting new customers. (Action) I listened to the Sales Director and asked questions about roadblocks he was feeling with his sales team. Then, I suggested gathering data to support the need before committing time and energy to a specific training topic. I recommended an anonymous employee survey to find out the most significant struggles the sales team was facing. This Director was unhappy with my suggestion because he wanted to see action immediately. I could tell that he was becoming increasingly frustrated with my more calculated approach. Feeling this, I explained to him that I was approaching this situation to clarify the problem and resolve the core issue rather than place a bandaid on the concerns and fail to solve his problem for the long term. I talked about how long-term results will fair much better for him and his team in the end. (Result) Because I remained calm during this conversation and showed empathy for this Sales Director's situation, he came around and listened to what I had to say. We took three days to create and send out the employee survey. Then, we took another week to analyze the results from the sales team of over 100 people. When the results came in, there was an overwhelming amount of evidence that morale was low among the sales team, and many of the employees were struggling with the CRM, which made client follow-up cumbersome. This data showed us that we needed to focus on CRM training versus prospecting. In the end, the Sales Director thanked me for taking a more mindful approach to this roadblock. We built a sales training tailored to the employee's struggles and delivered it with great success. In the following two quarters, the team exceeded sales goals by 9%, and they are on track to exceed goals in Q3. When paired with an individual who communicates differently from me, I take the situation as an opportunity to learn, grow and develop stronger professional communication skills. I have the confidence to take the initiative and share my perspective to reach common ground. It's important to have a strong relationship with my leaders built on mutual respect and clear communication. Does it sound to you that my communication approach is a fit for the leaders I will be reporting to in this role with Company ABC?"

      Heather's Answer for a Clinical Laboratory Technician Interview

      "I would describe my personality as approachable, light-hearted, and positive. I like to give more than I take and pride myself on being part of a team."

      Heather's Answer for a Bacteriology Technician Interview

      "In my career, I have had many different supervisors with an array of personalities. I did have one supervisor in the past who was not the type of leader that I would have chosen for myself. We disagreed on occasion but nothing severe enough to affect my work performance."

      Samantha's Answer for an Auditor Interview

      "I had a Manager who was rude to everyone. She would lay down what she thought was right and if you disagreed with her, you became the enemy and your schedule reflected it. I once suggested an improvement to scheduling to her and the general manager. While they considered it, my schedule went from day shifts to night shifts and double shifts for the next two weeks. I showed up to every shift with a smile and worked my butt off. My general manager noticed and assigned me as the restaurant's schedule maker. I still worked double shifts when necessary, but I tried to be as fair as possible."

      Neha's Answer for a Behavioral Health Technician Interview

      "I had a manager who I didn't see eye to eye with so I scheduled a meeting with him to see how we could work better together. After our meeting, ​we realized that it was just a miscommunication and we soon developed a great professional working relationship."

      Rachelle's Answer for a Warehouse Clerk Interview

      "In my current clerk role I am to place orders with four different vendors every Tuesday before 5 PM. It's important that I track our levels very carefully to avoid overordering since my company runs very lean. I have reminders on my computer to ask vendors about upcoming discounts or bulk-purchase opportunities. When you call my references, they will attest to the fact that I am always meticulous in my ordering and have solid relationships with each vendor."

      4 Community Answers

      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 Answer

      Good example.


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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 Answer

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

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