13 of the World's Hardest Interview Questions! (infographic)

Interviews are tough. And interviewing for the best jobs is really tough. So to help you gain a competitive edge in today’s job market, resume.io gathered the most thought-provoking interview questions from 13 top bosses and business founders. And it added some useful tips on answering them that will boost your chances of smashing that next interview!

You only know what you know

Elon Musk likes to get candidates thinking on their feet by slipping in this head-scratcher:

“You're standing on the surface of the Earth. You walk one mile south, one mile west, and one mile north. You end up exactly where you started. Where are you?”

It’s not a trick question; the answer is The North Pole.

But what if you don’t know the answer? Should you try to wing it? Definitely not. Instead, be honest. Admit you can’t find the answer and ask the interviewer to explain it. It demonstrates honesty, humility, and an inquisitive mind.

Who do you admire?

Who we aspire to be says alot about our values and personal ambitions. And that’s why Jules Walter, Product Lead at Slack, wants to know who his candidates admire the most.

It doesn't have to be a successful billionaire or famous celebrity. It’s the person’s values that matter; not their name or bank balance. Saying you admire a family member for overcoming a personal adversity is far more impressive than name-dropping a tech-giant.

Porter Braswell asks another value-led question. “What does success mean to you?” enquires the Jopwell founder.

Again, be honest. It’s the best way to see if you’re a good fit for the company and that the company matches your ambitions.

Talking about your failures

Chad Dickerson, former Etsy CEO, asks candidates to talk about a time when they screwed something up!

Pema Lin-Moore, VP of People Operations at WRA, asks a similar question: “What’s one critical piece of feedback you’ve received that was difficult to hear?”

Questions like this can feel uncomfortable, but they’re a great opportunity to display your resilience, problem solving skills, and sense of personal responsibility. So own up to your past mistakes, then talk through the steps you took to remedy them.

What’s your passion?

Laura Behrens Wu and Cindy Smith like to know what motivates potential employees outside of work.

“What are things outside of work you're irrationally passionate about?” asks Behrens Wu, the CEO of Shippo.

And Smith, Head of Strategy at Upstart, asks, “Tell me about a topic that you’ve learnt about yourself?”

Hobbies provide a useful insight into a person’s values and motivations.

Just don’t overdo it. Be passionate when talking about your extracurricular activities. But make sure your future boss knows that you’ll always put work first.

How honest can you really be?

“What would someone who doesn’t like you tell us about you?” asks Duolingo boss Luis Von Ahn.

Whatever you do, don’t say ‘nothing!’ After all, we’ve all got our faults. But do you know what yours are? And how are you planning to improve them?

Spanx CEO Sara Blackely is also interested in how candidates see themselves. She asks a simple question: “Describe yourself in three words?”

It’s surprisingly tough to answer, especially when it catches you off-guard. Start jotting some words and think about what they say about you.

Do your research!

Transformify CEO Lilia Stoanov wants to know how much a candidate knows about her company. So she asks candidates what they think about Transformify’s corporate values.

It’s a question that comes up in most executive job interviews. And there’s only one way to prepare: do your research!

Who would you hire?

Tim Chen, CEO of NerdWallet, likes to turn the table around during interviews.

“If you were me, what attributes would you look for in hiring for this role?”

Here, Chen is looking to see if you really understand the role you’re applying for and what it takes to succeed in the position.

Can you think differently?

Doing right is more important than thinking you’re right. That’s why 121 ventures founder Sarah Fetter asks this question in every interview:

“When was the last time you changed your mind about something important?”

It’s Sarah’s way of assessing flexibility and open mindedness - qualities that are essential in today’s fast-moving markets.

Show off what you’ve got!

The last questions come from Roli Saxena, President of advertising platform Adroll.

“What can you do better than most other people? What’s your superpower?”

Don’t be shy. Tell them how great you are and what you can bring to the company.

This is your time to shine; it’s what interviews are all about!

13 tricky interview questions asked by successful leaders (and how to answer them) - infographic
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