10 of the Best Interview Questions Ever

Diana-Martz by

When it comes to interviewing, if you want real answers you have to ask the right questions — the more unexpected, the better. Ten leading tech founders and CEOs share their favorite interview questions for picking out the best from the rest.

It’s no secret the impact great talent can have on driving your company to success. But when it comes to interviewing candidates, how do you really weed out the pretenders from the true contenders? Sure, you can go through the list of conventional interview questions — “Where do you see yourself in 5 years?” or “What are your strengths and weaknesses?” — but as these examples show, in order to truly find the perfect fit for your team, you’re going to have to dig a little deeper. And that means asking unexpected questions to get candidates off their scripts.

Want to know what questions companies Zappos and PayPal ask to find their dream talent? Read on! Below, we’ve compiled a list of ten of the most insightful interview questions from some of the most successful CEOS and founders in tech.

10 of the Best Interview Questions Ever

“On a scale of 1 to 10, how weird are you?”

Tony HsiehIt’s all about the candidate’s reaction to the bizarre question. Tony Hsieh, CEO of Zappos says, “Our whole belief is that everyone is a little weird somehow, so it’s really more just a fun way of saying that we really recognize and celebrate each person’s individuality, and we want their true personalities to shine in the workplace environment.”

Source: Quartz

“What book do you think everyone on the team should read?”

Dharmesh Shah“It’s a red flag if the candidate can’t think of a single answer.” Dharmesh Shah, Co-Founder & CTO of HubSpot, says, “Most great people always have had a book that they found to be super-useful and like sharing with others.” If a candidate can’t think of a single book, it’s likely he/she doesn’t enjoy reading or believe books are useful for learning. Both instances, Shah says, are worrisome.

Source: OnStartups

“What’s your superpower or what’s your spirit animal?”

Ryan HolmesThe silly question can give you insight into the candidate’s character. When Ryan Holmes, Founder & CEO of HootSuite asked his current executive assistant the question, she described herself as a duck because “ducks are calm on the surface and hustling like crazy getting thing done under the surface.” He says the amazing answer was a “perfect description for the role of an EA.”

Source: Fast Company

“How lucky do you consider yourself?”

Jennifer HymanThis behavior question helps weed out candidates that may be toxic to your culture. Jenn Hyman, Co-founder & CEO of Rent The Runway says, “appreciative people bring positivity to every interaction – a quality that is critical at a start-up.”

Source: Fashionista

“What do you know is true that no one else agrees upon?”

Peter ThielPair the question with, “What is a great business that no one has conquered?” Co-founder of PayPal Peter Thiel asks young entrepreneurs these questions because “You’re going to start a business you might as well try to start one where, if it works, it will be really successful, rather than one where you’re competing like crazy with thousands of people who are doing something just like you.”

Source: Elite Daily

“Think of something you’ve done in the past: What would you have done differently?”

Paul MaritaThe answer will tell you if the candidate is thoughtful or self-aware. Paul Maritz, CEO of Pivotal says if the candidate gives you an in-depth answer, it tells you “that this person thinks deeply and is honest enough to really be objective.”

Source: New York Times

“What are three things that really bother you but that most people don’t seem to mind? AND what are three things that you love and take great pleasure in that most people don’t like?”

Rand FishkinIt’s okay to break out of the formality of the interview. Moz’s Founder Rand Fishkin says that in addition to testing the candidate’s authenticity, the question also lets you see if your potential new hire is a value fit for your team.

Source: Rand’s Blog at Moz.com

“What was the first experience in your life when you realized you had the power to do something meaningful?”

Simon AndersonYou never know what answer you’ll get with an open-ended question. Maybe the candidate will tell you a story from when they were five or from their teenage years, says Simon Anderson, CEO of Dreamhost. “If someone sits there and they’re stumped, I think that tells you something.”

Source: Business Insider

“How much money would you leave us for?”

Ilya PozinThis provocative question weeds out candidates who just aren’t that passionate about your company. Ilya Pozin, Founder of Ciplex, says a great candidate will say he/she values a fulfilling job over money, a mediocre candidate will say double or triple the salary, and a bad candidate will choose less than double the salary.

Source: Inc.

“What questions do you have for me?”

Scott DorseyTiming is key with this classic question. Scott Dorsey, Managing Partner of High Alpha, loves asking this question really early in the interview. “It shows me whether the candidate can think quickly on their feet, and also reveals their level of preparation.”

Source: Inc.

Image by Stephen D

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VP, Human Capital

  • Those are indeed great questions to consider for identifying superstar talent. A few others I’ve found helpful include the following:

    Why are you considering leaving your current gig? We want to have a sense for what really drives the candidate – intellectual stimulation, a currently un-channeled passion, money, etc.

    Tell me about a situation where you made a bad decision and things went to hell. In this case, we really want to see a level of ownership (yep, I screwed up … and here’s how) as well how the person learned from this and was able to utilize the new learning in a future situation where things worked out well.

    Tell me about working with a horrible colleague (boss) and how you handled that situation. Here we are looking for the person not to project or create a scapegoat, but rather to see how they handle the real-world situation of dealing with difficult people. Are they confrontational? Do they swallow their frustration and walk away? What skills have they mastered for diffusing tension?

    Another technique is probing for a person’s developmental opportunities – a euphemistic term I prefer over “weaknesses” ;). Asking questions like, “What would mentors/advisers who know you best say are your top 3 development opportunities?” Obviously we are looking for thoughtful, genuine responses – ideally including action-plans the candidate has already put in place to begin working on them.

    I know a few CEOs who take final candidates out for dinner/drinks (or happy hour). As you’d expect, the conversation often starts our quite measured. But by the end of the evening, the candidate’s guard is lowered and a truer nature emerges. In the case of happy hours, I’ve had some CEOs tell me they disqualified candidates who couldn’t stay focused and maintain eye contact amidst all the people, chatter, and general hubbub of the environment.

    On the flip side, candidates are spending more time preparing for interviews and honing their answers. So great interviewers are able to cut through the “practiced responses” and get to the core of the candidate.

    -Anthony Gold (http://anthonysdesk.com or on Twitter @Anthonys_Desk)

  • DuchessofDownton

    I’m not working on Sundays, Brockman’s self righteous Sunday test or not. Sundays are for family. If he can’t appreciate the work-life balance, I don’t need to work for him.

  • This was a cool and thorough article, thanks for sharing!!