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How to Determine What Your Potential Boss is Like in an Interview

Ask your interviewer about why the position is open in the first place. (iStockphoto)

Most people assume that a job interview serves the sole purpose of being an opportunity for the employer to evaluate a potential employee. They see it as a one-way street, but it’s really not. The interview is not only a chance for an organization to get to know a candidate better; it’s an opportunity for a prospective employee to become more familiar with a company.

You may think that simply means you should be listening closely and looking around to see what the office environment looks and feels like. But you can and should take a much more active role in the process. Even as a prospective employee, you are allowed to ask difficult questions that will give you a better idea of the place you may end up working in. It’s not just a test of you; you are permitted to test them. What kinds of questions should you be asking?

[See: The 8 Best Questions to Ask a Job Interviewer.]

How did the position come to be open? This is extremely important. You may learn something that you were not expecting. On the other hand, the interviewer may dodge the question by saying something generic like, “Steve got a unique opportunity he couldn’t pass up.” If you’re having separate interviews with more than one person, ask each person the same question. When you get different answers from people, you’ll know that something may be up, and this is a pretty clear red flag. Even if everyone gives you the same generic response like the one above, try to obtain more information. Ask, “Where did this role end up taking him?” You can either infer something from the answer you get, or it may just become clear that there’s more to the story than they’re letting on.

You don’t want to find out after you start working that your manager is extremely difficult to work for. Asking this question of the people who work for your prospective boss may yield different answers than what human resources or a recruiter tells you.

[See: The 8 Stages of a Winning Job Search.]

What is the best part of working here, and what would you change if you could? This open-ended question could go in many directions. You’ll get an even better sense of the company if you ask several interviewers this question. Whatever their answers are, you should come away with a fairly good idea of how you align with their organization. You may hear about a benefit the company offers that you weren’t yet aware of, or something positive about your potential manager. By digging in for a negative aspect of working there, you’ll get a sense of what you may be up against, and from there you can decide whether that’s okay with you or not. It could be a deal breaker for you, or what they say may not bother you at all.

There are certain aspects of a job that would annoy some people but not others. Everyone is different. This gives you a snapshot of what is going on there and whether you are okay with it or not.

What does success look like for someone in their first year in this role? This should give you an idea of your manager’s or colleagues’ expectations. Bonus: It shows you are confident and results driven. It’s an important question because you may learn quite a lot from the answer. Perhaps you’ll be able to figure out if you are expected to work ungodly hours. It also may give you a sense of what your boss is like and how they manage their people. If their answer is vague and disengaged, it may be a sign that it’s not of the utmost importance to them, and you may have trouble down the road achieving the milestones and promotions that you expect.

While you may get a hot air answer, you will likely be able to tell if success and development is important to your potential boss. If the answer is specific to the job, you’re probably in good hands. If it’s generic, that could be a negative sign.

[See: The 10 Most Common Interview Questions.]

Unfortunately, many people will put a spin on answers to these questions. However, interviewers do not always expect these types of questions, so you may get some good, honest or inferable insights into the job and your boss’s character. Beyond the answers, look for other positive and negative signs during the interview.

Did your potential boss answer the phone or respond to an “urgent” email during your interview? Unless it was a family emergency or they are a doctor who needs to save someone’s life, it could wait. Did they politely listen to your questions and actually respond to the questions asked? If so, that’s a sign that they’re in tune with the people who work with and for them. If not, you may want to work for someone else.

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