8 Interview Questions That Elon Musk, Sara Blakely, and Other Top Execs Ask Job Candidates (and So Should You)

The best business leaders ask the best questions, especially when hiring new staff. After all, these are the people who will drive their company’s growth and success.

But savvy business leaders and execs aren’t always looking for a ‘right’ answer. Instead, they’re more interested in how potential employees handle the questions being asked. 

First of all, understanding what interview questions to ask is key. Equally important is knowing the intentions behind the toughest questions you’re choosing to ask.

Here’s a look at interview questions asked by successful business leaders. They were put together by online CV builder resume.io, with some helpful tips on answering each question effectively.

Tesla and SpaceX boss Elon Musk gets his candidates thinking with this brain teaser:

“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?”

The question tests scientific knowledge, logical thinking, and the ability to process new information quickly. It’s the perfect starter question for interviewing aspiring rocket scientists.

But it’s helpful in other ways, too, even if the candidate doesn’t know the answer. Someone who says “I don’t know, please explain” displays several positive traits, including honesty, integrity, and a willingness to learn.

Spanx CEO Sara Blakely asks a common (and deceptively simple) interview question: “Can you describe yourself in three words?”

It’s a way for Sara to get a good sense of a candidate’s self-awareness, values, and whether they’ll be a good fit for her company.

Candidates need to pick words that showcase their talents and suitability.

But don’t just listen for the words.

Candidates that interview well should take a little time to explain why they chose that word and why it’s relevant. For example, “I’m competitive. I thrive off challenges and being rewarded for all my hard work. It’s one of the reasons why I do so well in high-pressure, target-driven companies like yours.”

Chad Dickerson, the former CEO at Etsy, wants potential employers to reflect on their failures. He asks:

“Tell me about a time you really screwed something up. How did you handle it, and how did you address the mistake?”

It’s a tricky question designed to make candidates assess their past performances. It tests their ability to take responsibility for their professional and personal development.

Mistakes are natural. But what separates the best from the rest is how they react. They don’t search for excuses. Instead, they assess what went wrong and use the information to find ways of improving. 

Luis Von Ahn is another successful business leader who challenges job candidates with tough and uncomfortable questions.

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

Firstly, the question requires candidates to admit their personal and professional shortcomings. It tests self-awareness and humility. Would you hire or want to work with someone who thinks they’re perfect?

The second point of the question is to see what the candidate is doing to work on their weaknesses. The ideal answer outlines a personal fault and then reframes it into a positive by demonstrating what action has been taken.

Someone who was previously short-tempered could explain how meditation or mindfulness helped them become less reactive and more empathetic.

Roli Saxena, president of Adroll, takes a different approach. She wants people to shine during interviews.

“What are you better at than most other people?” asks the Adroll boss. “What’s your superpower, and how will you leverage that to make an impact at this company?”

Interviews are about showing off the best version of yourself. In other words, there’s nothing wrong with a little bit of boasting. But it must be done in the right way.

The trick is for candidates to focus on their strengths that match the job description. Listen for real-world examples and metrics to back up any claims.

Tim Chen, co-founder and CEO at NerdWallet, likes to turn the table around during his interviews. He asks, “If you were in my shoes, what attributes would you look for in hiring for this role?”

This is an opportunity for the candidate to prove that she understands her own skillset and how it applies to the position. Well-prepared job candidates will do as much research as possible and focus on the job description and company values.

Porter Braswell is the co-founder and CEO of Jopwell, a diversity hiring startup that connects companies with Black, Latinx, and Native American candidates.

He uses this thoughtful question to help candidates open up about what’s really important to them: “What does success mean to you?”

It starts a free-flowing conversation about the job candidate’s values and goals. As the interviewer, look for honesty and authenticity here even if it means they want to earn lots of money or win monthly sales competitions. And listen for clues about their desire to help others to succeed at work.

The more upfront candidates are about their goals, the better the odds of finding a good fit that will make both the new hire and employer genuinely happy.

Shippo CEO Laura Behrens Wu kicks off interviews with a question that appears unrelated to finding the right person for the job.

She asks, “What are some things outside of work that you’re irrationally passionate about?”

The question puts candidates at ease. But it also reveals what motivates them and whether or not their interests align with the company’s goals.

Listen for passion in their voice, but not misplaced and overdone passion. You want your (potential) future employee to convince you that work will always be their number one priority.