What the Interview Questions Of 5 CEOs Can Teach Us

When I was working as a house manager at a regional theater, I used to ask concessions stand interviewees what their second favorite Disney movie was. It always caught people off guard – it’s not something most people can answer off the top of their heads – and got at the heart of the interviewee’s character in a way that the standard “How would you deal with a problem customer” failed to do.

Earlier this week, I posted a list of basic interview questions you can expect to be asked, but along with those you’re likely to come across some real wildcards. These five are actually asked by CEOs, and the reasons behind them are fascinating. Even if you never interview at these companies, there’s a lot to be learned here about what hiring managers are trying to discover about you.


“When have you been most satisfied in your life?” – Dick Cross, founder and CEO of Cross Partnership

Assuming his more advanced interviewees possess the skills and smarts to the job, Dick Cross prefers to focus the interview on a person’s character and how well they match the organization.

This is a go-to question for him because, as he tell Jeff Haden, “This question opens the door for a different kind of conversation where I push to see the match between life in my company and what this person needs to be their best and better in my company than he or she could be anywhere else.”

The takeaway: Job satisfaction isn’t just important to your own happiness – your employer wants to make sure you’re a good match, too, in order to keep from having to search for your replacement.

Read more: The Strange, Difficult Questions CEOs Ask in Job Interviews by Jeff Haden


“If I were to ask people to describe you in three adjectives, what would I hear?” – Michelle Peluso, CEO of Gilt Groupe

For Michelle Peluso, the question “What are you not good at?” doesn’t do enough to cut through an interviewee’s rehearsed answer. Instead, she asks: “O.K., I’ve interviewed an eclectic crowd about you: the guy who delivers your food, the last people you worked with, the person who can’t stand you the most, your best friend from high school, your mother’s neighbor, your kindergarten teacher, your high school math teacher who loved you, and last boss. Now if I were to say to them, ‘Give me three adjectives that best describe you,’ what would I hear?”

If the interviewee snaps back with only glowing adjectives, she digs deeper. “It’s a tough question,” she tells the New York Times, “and nobody wants to answer it, really. But I do want to know, ‘What is top of mind for you?'”

The takeaway: Although you want to make sure you show up in a good light, try to be as honest as possible about yourself during the interview. Your potential employer will see through if you only praise yourself.

Read more: Michelle Peluso of Gilt Groupe: I Don’t Need an Ivory Tower (or an Office) by Adam Bryant


“A hammer and a nail cost $1.10, and the hammer costs one dollar more than the nail. How much does the nail cost?” – Jeff Zwelling, CEO and cofounder of Convertro

As the CEO of a marketing and advertising measurement services firm, Jeff Zwelling needs to know his employees can think on their feet – so he often asks this brain teaser in order to test that ability.

“Some candidates will instantly blurt out 10 cents, which is obviously wrong,” he tells Business Insider. “They don’t have to get the exact right answer, which is a nickel, but I want to see them at least have a thought process behind it. Ten cents is too easy of an answer, and if it was that easy, I wouldn’t be asking it.”

The takeaway: Although the pressure’s on in an interview, don’t just blurt out the first thing that comes to mind. Your interviewer wants to see how thoughtfully you solve problems more than how quickly you can answer.

Read more: Here’s The Tricky Math Question One CEO Asks To Size Up Job Candidates by Jacquelyn Smith


“Tell me something that’s true that almost nobody agrees with you on.” – Peter Thiel, cofounder of The Founders Fund

This tough question is designed to test an interviewee’s gumption, Peter Thiel tells Forbes. “It sort of tests for originality of thinking [and] for your courage in speaking up in a difficult interview context where it’s always socially awkward to tell the interviewer something that the interviewer might not agree with.”

The takeaway: Many interviewers are looking to see how well you perform under pressure – before you get into the hot water of your daily job. Tackle difficult interview questions with the same fortitude that you’ll bring to the job itself.

Read more: Reid Hoffman And Peter Thiel In Conversation: Finding The Best Candidates For The Job by Ryan Mac


“On a scale of one to ten, how lucky are you in life?” – Tony Hsieh, CEO of Zappos

The company culture at Zappos is known for being on the playful side, and CEO Tony Hsieh tells Business Insider that he works hard to keep it that way. Hsieh admits they’ve passed on talented people who were skilled, but simply didn’t fit with the culture, which is defined by values like “Be adventurous, creative, and open-minded.”

“How lucky are you in life?” is designed to test the value of open-mindedness. It was inspired by a research study that found the people who considered themselves unlucky paid less attention to a specific task than the people who considered themselves lucky. The way Hsieh sees it, it’s not about being unlucky or lucky, it’s about being open to opportunities beyond just how a task or situation presents itself.

The takeaway: Research a company’s culture before heading into the interview both to make sure you’re a good fit, and to understand how to answer interview questions about company culture.

Oh, and also remember that your attitude makes your own luck!

Read more: EXCLUSIVE INTERVIEW WITH TONY HSIEH: How Being A Little Bit Weird Made Zappos A Fortune by Henry Blodget

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