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uncomfortable interview questions

There are all sorts of interview questions out there, those that make us squirm, those that we’ve rehearsed over and over again, those that puzzle us and leave us scratching our heads, and oh so many more.  But, come every interview there will be a question that makes each person a bit uncomfortable, for whatever personal reason.

Maybe you had a bad prior work experience you don’t want to share, maybe you know you’re going to have to tell a white lie, or maybe you just don’t know how to approach the question.

In any event, you can learn to get through these situations without breaking a sweat and still come across as a stellar candidate.  Here are a few examples of uncomfortable interview questions to help you practice:

What do you think of your (current/previous) boss?

If you were in a negative situation, approach the question from a point of respect for the position and the company.  You might respond something to the tune of, “While we may have not always seen eye to eye, I respected my boss and his/her experience in the industry and learned from him/her on a daily basis.”

You don’t have to lie and you can always find something positive to take away, even from what may have felt like an un-constructive situation.

Whatever you say, the interview is no place to start down a path of negativity, no matter how much you may have disliked your previous employer or how much they miss-treated you.  Additionally, you don’t want to put thoughts in your future employer’s head that you’re going to spread damaging rumors around about them.

If you had a positive experience, great!  But, be careful not to sugar coat your prior boss too much.  You also don’t want your potential employer thinking you might jump ship at the first chance to go back to work for your old boss.

Try to tie in how much you’re interested in observing your potential employer’s management style or learning from their experience.

Why aren’t you earning more at your age?

Ouch, if you’re unlucky enough to get asked this in an interview, it can feel like a smack in the face.  But, don’t let the question catch you off guard or make you feel bad about yourself!

We all make personal choices about our career, and sometimes that can mean taking a job that fits into our current needs or career goals over taking a job with more pay.

Approach this question with the view that while you may not be earning what others at your level are, you are very satisfied with the career choices you have made, and that you were alright sacrificing the opportunity to make more money for the chance to learn different skill sets or to follow a passion.

Always stay positive and never let an interviewer feel like you should have taken any other path than the one you’ve chosen for yourself.  Don’t be defensive in your response, but show how you believe in yourself, your abilities, and your choices.

Your resume suggests that you may be over/under-qualified or experienced for this position. What’s your opinion?

Weigh your urge to share your true feelings regarding this question against how much you want the position.  In today’s job market it’s not uncommon for many people to take jobs below their experience level or for others to reach for jobs beyond what they’ve ever performed.

Even if you have more industry experience than the person interviewing you, hold your tongue and speak to why you want the role and why you are qualified for it.  Don’t avoid the white elephant in the room though, instead make it work for you.

You might approach the question starting something like this:

“While I may have held higher positions in the past, I view this role as an opportunity to get my hands back into the meat of the business  and re-hone my skills.  I value the opportunity to learn from position and grow with the company, while being able to apply my prior experience where I can.”


“What I may seem to lack in direct experience, I make up for in transferable skills and my in-direct experience.  You can see from my resume that I have held similar responsibilities in all of my previous roles that gives me a wealth of understanding of what it takes to be successful in this position.”

How long would you stay with us?

This can be a very tricky question, especially if you know that your time with the company will be short lived.  Whether you just need a job for the summer, have an internship lined up in a few months, or perhaps you’re planning to start a family or looking to take an extended vacation, none of these will sit well with a potential employer.

But, do you outright lie to get the job?  Even if you’re not planning on leaving the employer anytime soon, who’s to say how long you plan to stay?

A good approach is to say something along the lines that you plan to stay as long as you and the employer both feel that you are adding value to the company.

An answer like this helps reinforce that you want to be an asset and help the company grow, and you’ll give them every opportunity to keep you on board while always putting in your best effort, but should things not be in the best interest for either of you, you will understandingly part ways.

How successful do you think you’ve been so far?

This is another question that can have a person questioning themselves in the interview. Again, don’t let it unsettle you, especially if it never crossed your mind before to think about it.

Be positive.  Pick a few career highlights to point out and talk about how your path has lead you to this position which you feel is the right opportunity to help propel your career even further.

Reinforce your decisions and the career journey you’ve taken.  There is no one right path, and everyone gets to where they’re supposed to be in their own time.  You are your own success story.  Any missteps or side tracks in your career progression are not mistakes, they’re learnings, so if they come up, identify the valuable lessons you’ve applied to your future.

No matter what the question is that might make you uncomfortable, never let the interviewer throw you off guard.  If you need to, always take a moment, a breathe, to regain your composure or give yourself a moment to pause and think how best to approach the situation.

Never respond with a gut reaction or an overly-emotional response.  Be positive and thoughtful and if you find yourself struggling try to tie your response back into how fit you are for the position at hand.

Questions in the interview are only as uncomfortable as you make them.  A little laughter and appropriate humor can also be another way to break the moment of tension and let the interviewer see you ability to diffuse the situation in a positive way while you come to your answer.

So next time a question comes up that makes you uncomfortable in the interview, never let them see you sweat.  Stay poised and focus on the real goal–getting the job–and what response will help you get closer to that goal.


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