How To Answer 5 Tricky Job Interview Questions

Why do hiring managers ask tricky job interview questions? They ask because for them, hiring you is a risk. They try to minimize the risk by asking questions designed to uncover problems with you or your qualifications. Answer them well, and they will feel comfortable offering you the job.

Tricky Question #1 – Tell Me About Yourself

This is commonly asked in social settings, so many people respond with a social answer—this is a big mistake.

Always answer this question as if you were answering “Why should we hire you?” because that’s what they’re really asking. What will matter most to them?

  • Your education or experience?
  • Your skills? Maybe you’re a great communicator, a fast problem-solver or a skilled motivator.
  • Your achievements or awards?

So your answer may be something like,

“My background is in X, I am known for Y, and I have accomplished Z.”

Everything you mention should be a reason why they should offer you the job.

Tricky Question #2 – What Bothers You Most About Co-Workers Or Bosses?

Everyone has things that bother them, so it sounds false to say that you don’t. At the same time, you don’t want to seem negative, easily angered, or quick to embrace conflict.

Choose something very general that probably bothers most people, and be sure to speak about it calmly. For instance:

“I don’t like negative attitudes. It doesn’t help anyone, even the person who’s being negative. If there’s a problem, they should focus on how to fix it.”  That says you’re someone who’s focused on solutions rather than problems.

Tricky Question #3 – Why Have You Been Out Of Work For So Long?

Why haven’t you been snapped up—is there something wrong with you? Alleviate their fears by being positive and helping them see that is YOUR choice: you haven’t found the right fit yet.

If it’s true, tell them you took personal time before you hit the job search (maybe because you had a nice severance package), so you really haven’t been looking that long. Say that you’ve been on some interviews, but nothing that was a really great fit. As soon as you say that, say something like: “But it’s REALLY picked up lately, so I don’t think that I’m going to be in the search for much longer.”

That’s an important psychological tactic: everybody wants what someone else wants, so give yourself a little bit of that aura of unattainability by pointing out that you are going to be snapped up soon.

Tricky Question #4 – Why Weren’t You Promoted In Your Last Job?

Not getting promoted isn’t as bad as getting fired, but it still leaves the hiring manager wondering if there’s a problem with you. The best answer indicates that it was YOUR choice:

“I was offered a promotion, but I didn’t want to take on that additional responsibility.” Give them the reason—maybe you had small children, family obligations, or something else that may not be a factor now.

“I was offered a promotion, but I wasn’t interested in moving in that direction in my career.” If that promotion wasn’t a good stop on your career path, that’s OK.

Maybe the lack of promotion opportunities in your old company is exactly why you’re in the job search—so it makes perfect sense that you’re looking for advancement in another organization.

One thing that will help you any time there’s some question about your background: your references. Cultivate good references and prep them before your interview.

Tricky Question #5 – What Are You Most Proud Of?

The worst mistake job seekers make is answering this question with something personal: they completed the Ironman competition, or they’re proud of their kids.

Your answer to this MUST be work-related—and not only that, it must be specifically related to this job.

Think about your proudest accomplishments at work and choose one that would be especially impressive to this company, for this position (this is not necessarily the one YOU are the most proud of). Read over the job description and think about what may match up with those requirements. In your story, provide details—quantified if possible. Don’t be afraid to brag, and show your enthusiasm.  That’s what this question is for.

In all your answers, be strategic—everything you say in a job interview should give them another reason to hire you.

The best thing you can do for yourself is to prepare answers to as many interview questions as you can.