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Red-flag answers to avoid in hiring interviews, according to Tripadvisor's former CEO

Former Tripadvisor CEO Steve Kaufer.
Steve Kaufer, the former CEO of Tripadvisor, shared in a podcast interview the traits and red flags he looks out for in hiring interviews. Boston Globe/ Getty Contributor
  • Tripadvisor's cofounder discussed the traits and red flags he looks out for when hiring.
  • He suggested interviewees look out for questions about difficult projects and self-improvement.
  • He described curiosity and adaptability as crucial traits, especially in startups.
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Having a stellar résumé and LinkedIn profile is only half the battle to survive the job market. Nailing your interviews is a separate test — and the Tripadvisor cofounder Steve Kaufer recently shared some red-flag answers to avoid.

Kaufer, who stepped down as Tripadvisor's CEO in 2022 to found the philanthropy-focused startup Give Freely, spoke on "The Logan Bartlett Show" about his interviewing methodology and the traits he looks out for when hiring.

One go-to question he asks: What's the hardest project you've ever worked on? Kaufer said he listens for tendencies to blame others (a red flag) or an ability to empathize with coworkers (a green flag).

"That can often tell me, are they a team player?" he said. "It can tell me, are they ever taking responsibility for why something became difficult?"

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In other words, don't play the blame game in interviews, as it could suggest an inability to take responsibility when things get tough.

Kaufer said the answer to that question could also indicate differing definitions of hard work. For example, a candidate's viewing a task as difficult because they had to work on a Saturday could be "kind of a red flag," Kaufer said.

Kaufer said he looks not only at the obstacles interviewees struggled with but at their ability to constantly evaluate and improve. He said he'd often ask about successful projects and how a candidate might still refine them.

"That'll sometimes catch people off guard," he said. "And I can see kind of by the pause — they've never thought about it."

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Kaufer said he was particularly drawn to curiosity, which he uses to gauge interviewees' adaptability. He said an interest in the latest technology or trends could help indicate flexibility, especially in more unpredictable environments like startups.

"I don't know a good question for adaptability," he said. "I do know good questions for curiosity."

For example, Kaufer said he'd specifically ask interviewees whether they'd played around with new AI agents and chatbots. For Kaufer, it's important that a candidate demonstrate a willingness to adapt and curiosity about what's around the corner.

Software engineers who say they haven't experimented with AI usually get passed on, he said.

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"I just don't understand it," Kaufer said. "And I probably don't want to work with that individual."

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