5 CEOs share their favorite interview questions for potential employees

5 CEOs share their favorite interview questions for potential employees


Interviews usually unfold as if they’re following a ready-made script. They ask you about your greatest qualities and weaknesses, background, maybe a few more specialized questions, to which you answer in such a way as to be honest and accurate enough but also put yourself in the best light possible in the eyes of your employer.

This scenario can work for an entry or mid-level position, but for leadership positions, some CEOs like to resort to a more nuanced approach, and they choose interview questions that test and challenge the candidate’s mindset.

Roger Crandall, CEO of American insurance group MassMutual, told Quartz about his obsession with past failures in the lives of his job candidates. Crandall likes to look for honesty, resilience and humility in the people he evaluates in his interviews: “A person who can speak openly, honestly, and specifically about their personal shortcomings is attractive, but only if they can also explain how they are a better person, partner, leader, and manager as a result”.

Gordon Wilson, CEO of Travelport, a UK-based software company, spoke to the same news agency about the question he asks most often: Why are you here today?, to which he expects a very specific answer. “I’m surprised how many times people talk about the benefit of the job from their point of view, versus the benefit that they’re going to bring to the company”, he says.

Ken Moelis, the founder and CEO of Moelis & Co, an investment bank, likes to throw in a totally unexpected question such as What is your favorite property in Monopoly, and why?, so as to observe the candidates’ take on risk-taking and rewards.

Michael Gregoire, CEO of an IT management software company called CA Technologies, gives the standard leadership qualities question a Machiavellian touch. His most asked question is, according to Quartz, Would you rather be respected or feared?. He says that this question “never fails to catch people off-guard, and really reveals what they think about their leadership style”.

Zhang Xin, co-founder and CEO of SOHO China, a commercial property developer, shares with Quartz her favorite interview question. The self-made billionaire likes to ask her job candidates what their biggest dream in life is, and she considers that no answer is too ambitious, a fact of which she is living proof.