Job Interview Tips

How to Answer the Biggest Challenge Interview Question

tell me about a time you overcame a challenge
Written by Kate Lopaze

Part of the interview process is taking a frank look at challenges you’ve faced in your previous jobs. The interviewer is trying to figure out how you would approach problem solving in your new role, and see if there are any red flags. (Hint: “Dealing with the stupid people around me” is never gonna be your ideal answer when asked about previous challenges in your professional life.)

If the interviewer does ask you a question like, “What’s the most difficult part of being a [current job title]?” or “What was the toughest part of your last job?” here are ways you can frame it to make yourself look awesome.

DO think about this beforehand.

It’s a common enough question that the interviewer can reasonably expect you to be ready to think on your feet. If you need a review on some of the most common interview questions, head over to this article on the most common interview questions.

DON’T pretend your career has been a breeze up to this point.

It can seem tempting to make it look like you handled every issue with the ease of Roger Federer returning a serve–but making it seem like you never had any challenges or struggles won’t make you look like some kind of suave champ. It’ll make the interviewer think you’re a) not taking the question seriously; b) can’t think on your feet; or worse, c) being dishonest.

DO tailor your answer to fit the job description of the position for which you’re interviewing.

Unless you’re making a big career change or applying for a big stretch position, chances are your previous experiences will work nicely with the needs here. Before the interview, review the tasks and responsibilities associated with this job, and dig back in your mental archive for similar issues you’ve tackled in your current or previous jobs. Try to avoid purely personal anecdotes (about family or friend conflicts). The interviewer isn’t interviewing a buddy, he or she is looking for a strong employee.

DO be specific about why your challenges were challenges.

You want to show off your problem-solving process, so offer as much context as possible so that the interviewer can see how you’re connecting your past with your present (and ideally your future) professional self. Also, sum up with what you learned from the experience. (Example: After we got through the event totally shorthanded, I developed a “Plan B” coverage system that meant we always had backup in case we found ourselves in another crunch.)

DO make sure your anecdotes show you in a positive light.

You don’t get bonus points for brutal honesty here. If you were facing a challenge because of a mistake or because you dropped a ball, that’s not the one to highlight here. Focus on situations where your actions made you a hero (small h, no kitten rescuing necessary), not situations that featured you digging out of a hole you made yourself. Though even heroics aren’t necessary—if you were part of a team that had to solve an issue, and you took charge of any part of the process, that’s fine too. You want to demonstrate strong leadership and problem solving, whatever you choose to highlight.

DON’T panic if you don’t have a very long work history.

If you’re just out of school or are otherwise just starting out, this question can be daunting—how would you have had work challenges if you haven’t really worked yet? In this case, it’s totally fine to use an example from your education, or your volunteer work, or other activities (sports, extracurriculars, etc.). Again, though, make sure you tie it to your professional life, and especially the job description. Make sure it demonstrates your leadership skills, not your failures.

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About the author

Kate Lopaze

Kate Lopaze is a writer, editor, and digital publishing professional based in New York City. A graduate of the University of Connecticut and Emerson College with degrees in English and publishing, she is passionate about books, baseball, and pop culture (though not necessarily in that order), and lives in Brooklyn with her dog.

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