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How to Interview Your Potential Boss, 10 Questions to Ask

by THEA kelley | November 2, 2023

The #1 reason people quit jobs is their manager. So in job search, you need to know how to interview your potential boss and get a feel for whether you’ll like working with that person.

It’s fine to ask “What is your management style?” but the answer won’t tell you the whole story.

Here are 10 good questions to ask your potential boss in order to dig deeper. Use your best judgment at all times during this process. Remember, you’re not interrogating the manager – you’re having a friendly conversation!

Questions to Ask Your Potential Boss:

What are your goals for this position and your department?

You want to understand what’s important to your potential manager and how you can help achieve those goals. Ask this question as early in the interview as possible, so you can relate your other questions and answers to what you learn.

What do you most enjoy about working in this organization?

This may lead to insights about what this manager values, and also about the company itself.

What do you think needs to evolve in the company so that it continues to be a great place to work?

These questions may give you insight into the manager’s values as well as the strengths and weaknesses of the company culture.

How will you and I work together to make me successful in this role?

This may tell you a lot about the boss’s management style and what kind of support and training you’ll get.

In order for us to work well together, what should I always do, and on the other hand what should I never do?

This question must be asked with a smile! It’s a way of inviting them to air their hot-button issues, the things they feel strongly about – and the wording is very frank, which may encourage a frank reply.

What are some good ideas you’ve gotten from your direct reports, and how did they make a difference?

This may tell you how interested they are in such ideas, whether they act on them, and whether the company provides a fertile field for innovation.

What recognition, training and development have your direct reports received in the past year?

If they’ve received none of the above, this may not be a very motivating environment!

How much do you typically interact with your direct reports?

Many a new hire has been unpleasantly surprised to find that their manager is rarely available.

How do you like to communicate with your employees? By email, phone, texts, popping in with a question, weekly meetings, or some combination? What about when you’re traveling or in the field?

Listen closely. You may find out more than just whether to email or drop in.

May I ask about the person who was in this job before me – did they advance within the company or leave for a job elsewhere?

This may provide clues not only about your future boss but about the company and paths for advancement.

Of course, it’s easier to know what to ask if you’ve done some research on the boss ahead of time. Click this link for tips for doing a “reference check” of your own.

What to Do After You Interview Your Potential Boss

If the answers to these  questions raise any warning signs about the boss, you may want to look elsewhere – or proceed to the next job interview with your antennae up. If you decide the job is worth the downsides, at least you can start planning for how to work effectively with this person who will be so influential in your future. This article was originally posted in 2016 and has been updated. 

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