Former TripAdvisor CEO Reveals Interview Question That is an Instant ‘Red Flag’ If Answered Wrong

The former CEO of one of the biggest companies in the world has just let us in on his interviewing technique, and it’s going to make you think.

After launching TripAdvisor in 2000, Steve Kaufer remained CEO until retiring in 2022. After 22 years in the tech business as the big boss, the 61-year-old has learned a thing or two.

In an interview with Logan Bartlett for his podcast and YouTube channel, The Logan Bartlett Show, Kaufer shared his instant turn-offs in an interview and the characteristics he tries to avoid.

Kaufer urges any founders of small businesses to carry out the final interviews for any new employee themselves until their company reaches a few hundred people.

One of the first questions Kaufer asks candidates is: “Tell me about a really hard project, and why was it hard?”

This seems like a standard interview question, right? But with this question, Kaufer is trying to find out whether the candidate will blame their fellow team members or take some responsibility for shortcomings on a project.

This is an indicator of whether that candidate is a team player.

Kaufer is also listening for candidates who cite working overtime as a reason for a project being challenging. For him, this is an instant red flag as it doesn’t match his definition of ‘hard work’.

When it comes to personality traits, Kaufer looks for someone who is introspective. To identify this trait, he asks: “Tell me about a project that you’re really happy with and that was viewed as successful.”

Once again, it seems simple enough. But it’s the follow-up question that gets really interesting: “Given that that was clearly a win, if you had to do it all over again, would you do it exactly the same?”

This question, Kaufer says, ‘catches people off guard’ and he’s able to tell by their pause and reaction whether they’ve ever really thought about it.

This is another red flag for Kaufer, as he explains: “I’m looking for people that, whether a project worked or didn’t, are always in the mindset of self-improvement.”

The tech mogul also explains how he loves curiosity in his employees, so he will often ask them about hot topics related to the industry. For example, if he was interviewing someone in 2024, he might ask them if they’ve played around with any of the AI chatbots. He’s looking for people who are curious and ‘always interested in learning what’s coming next.’

A lot of CEOs seem to use simple questions to decipher a candidate’s true intentions. Similarly, Elon Musk famously asks the same question in every job interview to determine whether someone is lying or not.