10 quirky interview questions from the world’s top CEOs

Office & Culture

During the hiring process, companies today are looking not only for skills but also for the right “fit”. Does the candidate suit their company culture? Be it their end goal, ethical practice or simply office atmosphere, all companies have developed their own personalities and culture.

To find candidates that fit the bill, the world’s top innovators and board members are using clever and subtle questions in their interview process.

Here are 10 of the quirkiest questions from some of the world’s top CEOs.

1. “Would you rather be respected or feared?”
​Michael Gregoire – CEO, CA Technologies

Gregoire admits that while the question catches people off guard, it can be a trust test of character, as it “reveals what they think about their leadership style”.

While there is no truly correct answer, a more appropriate one can be decided based on assessing the culture of the prospective company. If the business fosters a collaborative and idea sharing environment, then it is best to be respected so that you may be heard.

2. “If I were to say to a bunch of people who know you, ‘Give me three adjectives that best describe you,’ what would I hear?
Michelle Peluso-CEO of Gilt Groupe

Peluso asks prospective candidates to provide adjectives from the point of view of “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 neighbour, your kindergarten teacher, your high school math teacher who loved you, and your last boss.

She believes this question evokes insight, as it requires candidates to think of their personal strengths and weakness outside of purely a work perspective.

3. “What century was the French Revolution in?” 
Stewart Butterfield – CEO,Slack

In posing this question, Butterfield wasn’t looking for the correct answer. He asked this question to gauge how interested candidates were in the world around them.

Now he only asks what the candidates want to be when they grow up. “Good answers are usually about areas in which they want to grow, things they want to learn, things that they feel like they haven’t had a chance to accomplish yet but want to accomplish,” he believes.

4“Talk to me about when you were seven or eight. Who did you want to be?”
Barbara Byrne – Vice Chair, investment banking, Barclays

By the time a candidate reaches the interview with Byrne she assumes they’re already intelligent enough for the role. Rather than assess capabilities, her questions aim to “connect to the real person” underneath. As such, she believes childhood dreams are the best and quickest way to get to know someone.

5. “What magazines and books have you read recently? What do you do in your spare time?”
César Melgoza – CEO, Geoscape

Melgoza considers this question a good way of finding out what motivates a candidate to improve. When asking this he is really trying to find out “are you investing in yourself” outside of your job?

6. “What part of this role do you love and you can’t stop doing? And what part do you hate doing?”
Christa Quarles, CEO, OpenTable

Quarles uses this question to assess if the candidate has a passion for what the job entails, as she believes that excitement leads to engagement. When posing it to applicants, she wants to see “is the majority of the job something they would want to do even after the kids go to bed, because it is something they are engaged and engrossed by.”

7. “We finish the interview and you step outside the office and find a lottery ticket that ends up winning $10M. What would you do?”
Dror Malton – CTO Yufit (2011)

Again this is an example of the prospective employer trying to find out what makes a candidate tick.

“There’s no right answer; I’m just trying to see what makes the person tick [ …] Some people are quite uncomfortable with this question because they can’t figure out what’s the right answer,” Malton says.

People hangout together at coffee shop

8“What is your favorite property in Monopoly, and why?”
Ken Moelis – founder and CEO, Moelis & Co.

Moelis throws often throws this curveball at mid-level applicants to see how they can respond to something light hearted in a serious setting. He considers it a “great way to hear how people think of risks and rewards”.

9What’s your biggest dream in life?”
Zhang Xin of SOHO China

As a self-made billionaire who started her working career in a garment factory in Hong Kong, no dream is too big for Xin. The iconic commercial property developer says she is attracted to “free spirits” and likes candidates who have ambitious goals beyond their current situation.

10.“What did you learn from your mom?”
Lars Dalgaard – Venture capitalist, Andreessen Horowitz and former CEO, Success factors

Dalgaard says when asking this question, “basically I’m testing them to see, ‘How human are you ready to be with me?’” He uses the question the probe how emotional a person is and how they can control and deal with those emotions.

Although these questions might seem more ‘quirky’ than your standard interview queries, they serve to show employers what candidates are made of, and whether or not they will fit with the company culture that has been created.

Here at Glandore, we believe in providing the space and structure for companies to keep their own culture. Our events and wellness initiatives are carefully selected to compliment our member companies’ values and needs. 

If you would like to find out more about member community, click here. We would love to welcome you to the Glandore family!

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