Job Interview Tips

How to Answer the Toughest Interview Questions

Written by Kate Lopaze

The toughest interview questions can be deceptive—after all, how can “tell me about yourself” be a trap? In reality, these are questions that require some thought behind them, and that means you don’t want to look like the proverbial deer in headlights while you scramble for an answer.

Here are some of the most common tough question types, and how to get through them.

What is your biggest weakness?/Tell me about a time you failed./What is your greatest missed opportunity?

These are questions designed to get you to be honest, and to (unofficially raise any red flags for the interviewer). They’re kind of a trap. If you say you don’t have any weaknesses or failures, they’re likely to keep digging until you reveal something you might not want to reveal. If you use a blatantly positive “weakness,” like “I love my job too much,” that will likely also result in more pushing for the real you.

Instead, confront these questions head-on. Before the interview, prep some examples of times you faced adversity in your job, but that you persevered. Find a way to turn it into a backdoor positive: “My weakness is that I try to take on too much, but I’ve learned along the way to trust the people around me and work on realistic plans to get the job done.” Or “I used to have issues with organization, but now I’ve developed a planning method that works for me, and I also take advantage of tools like Asana to keep me on track.”

Are you a team player?/Tell me about a time you handled conflict./What would you do if you disagreed with your boss?

These questions are meant to gauge your ability to work with others. Incorrect answers include: “There’s no ‘I’ in ‘team,’ right?” However, you also don’t want to look like a middle-of-the-pack pushover. The best way to handle questions like these is to have specific examples of how you’ve collaborated with others in the past. If you were the leader, make sure you emphasize that, and talk about how important it is for the whole team to work well together and put aside differences so that the work gets done.

Aren’t you overqualified for this position?/Where do you see yourself in five years?/What are your long-term goals?

 These are commitment questions. The last person a company wants to hire is someone who’s going to bolt for a new opportunity six months in. Realistically, the interviewer knows you’re not likely to put in 50 years in this job, but it’s good to reassure him or her that you’re committed to the idea of this role. The answer to the long-term question doesn’t need to be, “I see myself right here in this position,” but definitely talk about how you see yourself growing into the role and what your professional goals are in the industry.

The “overqualified” question can be especially sticky, especially in a tough job market were people just want a foot in the door. If that’s the case, be honest that you’re seeking a position where you can settle in and build a new arm of your career, picking up new experiences and bringing your skill set to this new job, even if it’s a step back in seniority.

If you practice these kinds of questions beforehand, and have a mental list of specific anecdotes and points you want to hit in the interview, the interview should go more smoothly. You never want to be caught by surprise, lest you start rambling or admitting to things that make you look like a weaker candidate. Always find a way to spin answers to these questions as either a strength or as a learning experience, and you’ll do well on interview day.

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.