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The curveball interview questions CEOs are asking job seekers amid Gen Z’s hiring nightmare

January 7, 2026
in Business
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The curveball interview questions CEOs are asking job seekers amid Gen Z’s hiring nightmare

It’s no secret that getting a new job is hard, with candidates constantly complaining about the endless hoops that recruiters are making them jump through to prove they’re the perfect match, from endless rounds of interviews to 90-minute tests and presentations. 

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But for young people in particular, the challenge is even steeper. About a fifth of Gen Zers worldwide are classified as “NEETs” and are currently locked out of the job market. Last year in the U.K. alone, more than 1.2 million applications were submitted for fewer than 17,000 graduate roles. 

Even Goldman economists have admitted Gen Z’s hiring nightmare is real—and it isn’t going away anytime soon. 

As millions of Gen Zers face unemployment and entry-level office roles becoming scarcer, hiring managers are being forced to get creative to find the very best candidates. So Fortune has rounded up the curveball make-or-break interview questions now shaping hiring decisions.

Do you think we are in an AI bubble?

Do you think we’re in an AI bubble? Even the experts who’ve predicted past crashes can’t seem to agree. But if you’re looking for a job right now, your opinion on all this could decide whether you get the job. Dave McCann, IBM’s managing partner for EMEA, says he now throws the curveball question in interviews as a make-or-break test.

There’s no right or wrong answer, but actually knowing where you stand could give you an edge and pique the exec’s interest. McCann doesn’t care which side you pick—he cares whether you’ve thought it through.

Can you design a car for a deaf person?

Lyft CEO David Risher likes to ask candidates: “Design a car for a deaf person.” The curveball question may sound unusual, but for Risher, it’s a quick way to “suss out” whether a candidate can put themselves in the shoes of a customer—and he got the idea from his time working with Jeff Bezos. 

“I want to see the candidate close their eyes and ears and imagine what that feels like, then be able to describe the experience to me in detail, including what someone in that position might need,” Risher said. “That’s how I know I’ve got someone who can build great customer-obsessed experiences.”

Do you have any questions for me?

The question that turns its head on the interviewee and enables them to put the hiring manager in the hot seat isn’t an unusual one. But for Twilio’s CEO Khozema Shipchandler, it’s what comes next that matters most. 

If your answer is a blank stare or “Nope, I’m fine,” consider yourself on thin ice. 

“The number one red flag for me is when someone doesn’t ask questions towards the end of an interview,” Shipchandler exclusively told Fortune. “That’s a pretty significant mark against them being curious about what they’re interviewing, the company, the way we might work together, chemistry, culture, all of those things.”

And Denny’s CEO Kelli Valade echoed that it doesn’t really matter what you ask employers at the end of the interview—the fact that you do ask something shows you did your homework, are seriously interested and is a big green flag.

Can you start right away?

Picture this: You’ve spent hours applying for the dream job and sitting through multiple interviews. Finally, you think you’ve won over the hiring manager when they ask, “when can you start?” 

You’d be forgiven for thinking the right answer, is “straight away.” After all, you want to seem eager. But Gary Shapiro, the chief executive of U.S. trade association Consumer Technology Association, revealed that he turns candidates down who say they’re available within two weeks. “They don’t get the job, because they’ll treat us the way they treat that former employer.”

Other things to look out for: Coffee cup tests, pricey menu items and wait staff

It’s not just what you say in the interview that could cost you the job. Hiring managers are also watching what you do—as early as when you walk through the revolving doors and great reception. They’re looking at how you treat staff before and after your interview, as well as, what you do with the coffee (or tea) cup you were drinking from. Hint: offering to clean it up will go down will.

Other hiring managers take their prospective new hires out for a lunch interview and watch for whether they season their food before taking a bite. Why? Because putting salt (or anything) on your food before tasting it is the equivalent of judging a book by its cover and apparently, highlights a lack of patience.

That’s not all. They’re also testing you for how quickly you order, whether you wait for others to sit before sitting down to eat, the price of the items you order, and how you treat wait staff.

One consultant even revealed on X that he knows a CEO who goes as far as taking candidates for breakfast and secretly asking the servers to mess up their order “to see how they’d react.”

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