Tough interview questions: ‘Who was your best and worst manager?’

Editor’s note: This article is one in a series on how to answer some of the toughest job interview questions. Read previous articles on answering interview questions on such topics as your greatest weaknesses, your salary expectations, and why you are leaving your current job.

During an interview, hiring managers may ask you for some feedback on past bosses, and this can feel like an uncomfortable question to answer. It’s easy to share compliments about a former boss who was a good manager, but it’s harder to know what to say about a boss who was difficult. Here are some guidelines for providing a good response:

What the hiring manager wants to learn

Asking for feedback about former managers is a way for hiring personnel to gauge how well a candidate would thrive in their office, said Michael Steinitz, Washington, D.C.-based executive director for accounting staffing firm Accountemps. When they ask this question, they have “their own leadership team’s and manager’s qualities” in mind, he said.

The question also uncovers your professionalism, said Nicole Gable, chief of sales for Accounting Principals, a national accounting staffing firm based in Jacksonville, Fla.

“They want to see how you will deliver a potentially critical assessment of a former manager or a working situation and what you have learned from this experience,” she said. “It will give the interviewer a sense as to what kind of employee you will be.”

What are some good strategies for answering the question?

Knowing the reason for this question can help you craft your answer. When discussing your best manager, Steinitz recommends sharing what the person did to help you develop in your career.

“How did you improve and grow as result of working for that person?” he asked. Your answer shouldn’t be about how you feel about the person but about “how they brought out the best in you,” he said.

Be honest, even if it means admitting weaknesses you had in the past, said Gable. “Give an example of a manager who helped you grow and develop as a professional — a person who pushed you out of your comfort zone, helped you reach a new potential, or taught you a business or leadership lesson,” she said. “Use this time to let the hiring personnel know you are a person who is looking to learn, grow, and work hard.”

When discussing your worst manager, choosing someone in the more distant past may be a strategic, safe route to protect the person’s identity, said Gable.

“Keep in mind, however, that how you characterize why you feel negatively towards them will be very telling,” she said.

For example, suppose you had a boss who was never available due to organizational changes. In that case, Gable suggested saying that you regretted not having an opportunity to learn as much from them as you had hoped.

Tone down any bitterness or anger you may have, said Steinitz. “I would speak to what you could have done differently to make the situation better,” he said, and to avoid conveying the idea that you had a personality conflict with the manager.

In fact, it may not be helpful to think in terms of “best” and “worst” managers at all, said Andrew Broderick, CPA, manager at independent CPA firm Schellman & Company LLC, in Columbus, Ohio.

Early in his career, he said, he might have described his “worst” manager as one who gave him too much work. Now, he takes a more nuanced view of the question. 

Each manager has something to offer, Broderick said. “As a professional, the people that tell you what you do not want to hear are often the people who can help you grow the most — if you are open to it,” he said. “Thinking in terms of best and worst might make for entertaining water cooler talk, but looking internally and doing your best to take the emotion out of it” will better help you to answer this interview question.

What not to say

Under no circumstances should you ever share a previous manager’s name or give any information that would lead the interviewer to know whom you are talking about, said Gable.

“People’s networks are large, and you may effectively kill your chances of a job by oversharing,” she said. “No one wants to hire someone who enjoys complaining about negative experiences.” Instead, she said, they want to hire those who “learn from the past, are professional, are compassionate in their assessments of others, and are looking to work for leaders who will help them be their best selves.”

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— Stephanie Vozza is a freelance writer based in Michigan. To comment on this article or to suggest an idea for another article, contact Courtney Vien, a JofA senior editor, at Courtney.Vien@aicpa-cima.com.