- Indeed’s CEO Chris Hyams has asked over 3,000 job candidates the same question for the past 15 years: Apple or Android? It’s a deceptively simple question, with no right answer, but the job platform’s boss says it flags their decision-making process. And he’s not the only CEO who resorts to unusual interviewing tactics. The leaders of TripAdvisor, StockX, and CTA ask about hardship, starting dates, and clocks to pick their new hires.
Job seekers have to jump through a million hoops to land an opportunity in 2025—and sometimes, it all hinges on one nerve-wracking question. Indeed CEO Chris Hyams says he has a deceptively simple test that he’s used with over 3,000 candidates over the past 15 years.
“It might seem strange, but I ask everyone, ‘Do you have an iPhone or an Android, and why?’” Hyams tells Fortune.
It might seem like a trick question, but the job platform chief says it’s more of an icebreaker that can reveal a lot about an applicant. There isn’t one “wrong answer” that could cost them the job.
“I’m mostly curious about how people make decisions,” Hyams explains. “And it’s actually a long 15-minute series of back-and-forth on this, where I get to learn a little bit about the human being, and about how they make decisions.”
Most people answer iPhone, with typical reasoning being they’ve stuck with the brand since being put on their family plan in high school. Others open up about the apps they enjoy using on their phone, generally, giving Hyams a peek into their passions. When that happens, he also asks what they would change about the platforms.
“You can actually have a really interesting set of conversations around how important it is when you choose a product, that you can get stuck with that thing for a very, very long time,” Hyams says. “I ask people what apps they use, and that’s a way to learn a little bit about them.”
CEOs have trick questions up their sleeves to field talent
Hyams isn’t the only CEO with a make-or-break interview question. Stephen Kaufer, the cofounder and former CEO of TripAdvisor, asks candidates one thing to see if their work ethic and personality would mesh well with the company’s culture: “Tell me about a really hard project, and why was it hard?”
“That can often tell me: Are they a team player, are they ever taking responsibility for why something became difficult? It can tell me their definition of ‘hard,’” Kaufer said in a 2024 interview with The Logan Bartlett Show.
Kaufer’s question is echoed by Wisp CEO Monica Cepak. The leader of the reproductive telehealth company says she always asks: “What’s the hardest problem you’ve ever solved at work, and how did you reach a solution?”
She looks for team players who work across different departments—if a candidate only boasts about doing things by themself, they get the boot.
Meanwhile Gary Shapiro, CEO of $115 million Consumer Technology Association, brings a lot of weight to an interview standard. He asks “How soon can you start?” but how a candidate responds says more than just scheduling. If the interviewee answers they can start in less than two weeks—and they’re currently employed—they don’t get the job. Shapiro says it signals that the applicant isn’t loyal to their employer, and that he would likely get the same treatment.
Other CEOs ask some pretty unusual questions to keep candidates on their toes. StockX CEO Scott Cutler asks, “How many degrees separate the minute and hour hands of a clock at 3:15?” He wants to see how candidates think under pressure; it’s not about getting the answer right, but more about how they respond to problem-solving on the spot.
5 make-or-break interview questions job seekers can prep for
- Do you have an iPhone or an Android, and why?
- Tell me about a really hard project, and why was it hard?
- What’s the hardest problem you’ve ever solved at work, and how did you reach a solution?
- How soon can you start?
- How many degrees separate the minute and hour hands of a clock at 3:15?