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

Tell me about the worst manager you ever had.

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Tough Interview Questions & Answers

  1. 1.

    Tell me about the worst manager you ever had.

      How to Answer

      Everyone has had that one boss that nearly drove them crazy. If you haven't - consider yourself lucky! At the very least, you probably know someone who had a manager with which they did not mesh.

      Your worst manager may have been someone who didn't know how to take the lead. Maybe they lacked confidence or training. Talk to the interviewer about an experience you've had with a manager who was not a strong leader. Be sure to end on a positive note and avoid allowing this to become an opportunity to bring someone down.

      Rachelle's Answer

      "Earlier in my career, I had a manager who was not a team player. My colleagues and I did not know how to react to the lack of leadership which meant that much of what we did was self-taught. I always told myself that if I were a manager, I would be a knowledgeable one who would encourage my team to be the best. Although my experience wasn't amazing, I am thankful for the opportunity to learn the type of behaviors to avoid as a manager."

      Rachelle's Answer for an Admin Interview

      "I am proud to say I have never worked with a manager or leader I could not respect or look up to in some form of mentorship. I imagine a terrible manager to be disengaged, lack communication and have a poor ability to build relationships with their team or business."

      Rachelle's Answer for a Manager Interview

      "One of the first managers I had was not well equipped for her role - she simply wasn't trained, so I do not fault her for that. However, she spent her days complaining about her lack of training rather than seek it out herself. I am a major proponent of research and feel that a good manager will find a way to make their position a successful experience."

      Rachelle's Answer for a Marketing Interview

      "I'd have to say the worst manager I've had is someone I'd describe as really aloof. He would breeze in and out, was rarely around during the work day and would drop in to take credit for any sales. So, not only was he not supportive, but also he then acted like he was integral to the sale. It was certainly frustrating, but it taught me that I could figure out a way to thrive and be successful with or without active leadership."

      Rachelle's Answer for a Retail Interview

      "I feel very fortunate that I've typically had great managers. However, I had a manager when I worked in the college restaurant that came on much too strong. She felt the need to try to whip everyone into shape and be overly controlling about everything. I'm all about order and following the rules, and respect for new managers or management in general. However, there's a way to gain the respect of an existing workplace without berating employees. That said, it taught me how to interact with someone aggressive and to show respect regardless of whether it feels warranted or not."

      Rachelle's Answer for a Sales Interview

      "Early in my career, the company restructured and promoted someone into a management role without any real basis for the promotion. It appeared that the promotion was on favoritism rather than leadership and management traits. The new manager didn't do anything terrible, but just basically continued being a sales guy who was supposed to be managing and didn't want to. I sought out a mentor and looked to him as though he were my manager in many ways. Through this mentorship, I learned what I valued in a manager and the type of manager I wanted to be. I decided to be level-headed but passionate, knowledgeable but not a know-it-all, hands-off until someone needs intervention or asks for help, and fair. If it weren't for my inexperienced manager, it would have been much later in my career that I found such a valuable mentor, so for that, I am grateful."

      Rachelle's Answer for a Teacher Interview

      "Before becoming a teacher, I worked as a bartender. The bar owner was a real hot-head who loved to drink with the regulars. This sociability was fine; however, it often got in the way of his success because he would become belligerent towards the staff and they would quit. He lost a lot of customers because of his behavior as well. I learned from the experience that when you are in a position of leadership, you need always to be aware of who is watching you and act accordingly."

      3 Community Answers

      Anonymous Answer

      "I did not work for him that long. He had a different agenda that was not very clear to me, and we were challenged in overcoming our communication issues despite multiple attempts."

      Rachelle's Answer

      It sounds as though you remained professional, regardless of the situation — a nice way to respond.

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      Anonymous Answer

      "My company restructured and promoted someone into a management role without any real basis for promotion. While she certainly worked hard, it was clear to the team that her temperament wasn't fit for the position. During a POA, she lashed out at one of our teammates and made an example of her in front of everyone. One of my colleagues resigned after only six weeks. I sought out a mentor and looked to her as my manager in many ways. Through this mentorship, I learned what I valued from a manager — someone who was even-keeled, fair, and could articulate the expectations from the leadership team. Had I not had the experience of a poor manager, I never would've found such a valuable mentor, and for that, I am grateful."

      Rachelle's Answer

      The fact that you sought out a mentor, and learned from this unpleasant experience, will certainly impress the interviewer. Great job relaying the example well so that you do not even come close to bashing the manager personally. Fantastic professional balance.

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