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How To Talk About Your Past Bosses In A Job Interview

How To Talk About Your Past Bosses In A Job Interview

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Talking about your previous boss to your potential new boss in a job interview can be tricky.

Related: 5 Things Every Employer Wants To Hear In An Interview

Here Are 4 Questions You May Be Asked About A Past Boss Along With Great Answers.

1. Have you ever had difficulty working with a supervisor or manager?

We all know that we should never answer an interview question negatively, but what do you do when a question practically demands a negative answer? Don’t be negative. It says more about your attitude than it will about your former boss. If you can truthfully say you’ve never had trouble, then say so. If not, give a neutral-to-positive answer, such as: “In my very first job, I had a little trouble. I didn’t know enough to clarify expectations before I started, and it ended up being an issue. I got some advice from someone with more experience than me to go and speak with my boss about what was going on. That turned out to be the best move I could have made, because we cleared the air and were able to move forward. It turned out to be a great lesson for me about the importance of clear communication right from the start.”

An answer like this one is a very positive one. It doesn’t lay the blame on the boss, and is very relatable. Who hasn’t had trouble over poor communication or unclear expectations? Most importantly, this answer tells what you learned from it and how you became better as a result of this experience.

2. Who was your best boss and who was your worst?

When you talk about your best boss, a great answer will focus on what you learned from that person that will help you be successful in this new job.  For example: “I’ve had some great bosses I’ve learned a lot from. One in particular was…” and then you can talk about a skill, a good habit, or something else that will contribute to your success in this new job.

When you talk about your worst boss, stay positive. As much as you can, avoid specifics with this answer and concentrate on communicating that you are adaptable and get along with a wide variety of people. You may say something like: “I once had a boss who was hired after I’d been working there for a while, and our communication styles were very different. I got along OK with her, and I succeeded in my job, but it wasn’t as great a relationship as I’ve had with other managers.” You aren’t badmouthing this person, and you’re pointing out that you were able to get along and be successful.

3. Tell me about a time you disagreed with your boss over how something should be done.

There’s probably no one who’s ever worked who always agreed with the boss on how everything should be done. This is a good opportunity to explain how you can be diplomatic and respectful, and put forward an idea without bashing someone else’s.

A great answer might sound something like: “My boss made a decision to move forward on something that I could see would cause us a lot of problems down the road. So, I went to her and told her about my concerns, along with some alternative ideas that we could think about. She appreciated that I had come up with thoughtful solutions, and ended up implementing one of my ideas. It worked out well, and we got XYZ results.”

Every time you tell a story, make sure you end with the results you got from your actions. This is an important thing that hiring managers pay attention to.

4. What would your manager say was the area you most needed development in?

This is another version of “What’s your greatest weakness?” The best answer to this question (as in any question about your weaknesses) gives an answer that clearly is a weakness, but won’t harm your job performance in this new position. For example, I was in sales, so I always gave impatience as my weakness. Impatience is a problem in my personal life (just ask my kids) but drives me to make the sale.

If your current boss will be one of your references, talk to him or her ahead of time and make sure you are both on the same page.

Always be strategic in your interview answers and sell yourself for the job. Find more than 200 job-winning answers in How to Answer Interview Questions and How to Answer Interview Questions II, available on Amazon.

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About the author

Career Coach – Peggy McKee is an expert resource and a dedicated advocate for job seekers. Known as the Sales Recruiter from Career Confidential, her years of experience as a nationally-known recruiter for sales and marketing jobs give her a unique perspective and advantage in developing the tools and strategies that help job seekers stand head and shoulders above the competition. Peggy has been named #1 on the list of the Top 25 Most Influential Online Recruiters by HR Examiner, and has been quoted in articles from CNN, CAP TODAY, Yahoo! HotJobs, and the Denver Examiner.


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Peggy McKee Career Coach – Peggy McKee is an expert resource and a dedicated advocate for job seekers. Known as the Sales Recruiter from Career Confidential, her years of experience as a nationally-known recruiter for sales and marketing jobs give her a unique perspective and advantage in developing the tools and strategies that help job seekers stand head and shoulders above the competition. Peggy has been named #1 on the list of the Top 25 Most Influential Online Recruiters by HR Examiner, and has been quoted in articles from CNN, CAP TODAY, Yahoo! HotJobs, and the Denver Examiner.