How to Answer 5 of the Toughest (and Most Awkward) Interview Questions

Interviews are the most terrifying 8-12 minutes of your life and if you’re lucky, they’ll be the most terrifying moments of your life through three rounds of upper management second interviews or callbacks and you’ll eventually get your dream job.

The key to staying cool under pressure is being prepared for the intimidating and sometimes downright strange questions you are asked.

Monster polled young professionals and found some of the most awkward interview questions. Here’s the best advice on how to knock these curveballs out of the park.

Q: What would I find if I Googled you?

1. Do not lie. 2. Before you interview, update your social media settings to private if you feel there’s anything questionable.

Your social media can’t do much to help your job search and it can do a whole lot to hurt you. Regardless of how private your accounts are (they should be protected like missile codes) this question might come up. Thus, make sure that you can say with confidence that you project the same professional image online that you do at work. The closer this is to the truth, the more confidence you’ll have in saying it.

Q: What would make you quit this job?

This is very much a loaded trick of a question. It’s actually a very good one because it puts you on the spot and helps them weed out those who aren’t interested. A diplomatic answer would be to say, “If I felt I wasn’t contributing enough to the vision of the company.” You can add variations, but you should make it clear that you will be putting the company’s best interests first.

Q: Name a time you’ve personally failed but persevered through it anyway.

This is a pretty excellent question because it gauges how hard you screw up and how well you problem solve (a skill essential to pretty much everything). Be sure to have an anecdote ready. One of mine is: “On my first film project the school’s camcorder was stolen from my backpack. I had hidden it well but somebody was on a mission. I was also on a mission and I had to get the movie made. I had to use a semi-broken old camera we had at home which meant paying that much more attention while shooting. Ultimately, I made exactly the movie I wanted to and learned a valuable lesson in keeping track of the important things.”

It’s hard to not make yourself look bad with the first part. I’m certainly embarrassed by my screw-up, but the perseverance and eventual success is key. I used this story as my college essay and in interviews all the time. A similarly vulnerable but ultimately endearing anecdote should do the trick.

Q: What’s your weakness? Pause… Nope. Keep going.

“What’s your weakness?” is a very common interview question and once again, quite tricky. My go-to is “I have a hard time being concise especially in emails. I was raised by writers and write a lot, but I always notice my emails are longer than the responses. So I’ve been trying to be more short and sweet so as to be less demanding of people’s time.”

While it is important to be as concise as possible in your work correspondences, this is a pretty excusable weakness, which is key. Whatever you choose to go with, make sure it is indeed a weakness, but don’t tell them your deepest darkest secret.

Q: Do you have a girlfriend? Boyfriend?

This is an extremely important point in the interview: you are interviewing your potential employers as well. While everyone in entry level will have to compromise a bit of their ultimate goals (if only to pay your dues on the way to achieving them), there are limits.

You should never have to disclose your sexual preferences. While there are different variations of the truth we all know we tell in interviews, you should never find yourself in a position where you have to flat out lie about an important piece of who you are to get a job. If you can’t be yourself at work, chances are you won’t enjoy working there.

Monster Wants to Know: What are some of the toughest or most awkward interview questions you've been asked? How did you answer? Share with us in the comment section.