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

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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. 

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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Trump order says Venezuelan oil money is being held by US for ‘governmental and diplomatic purposes’

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President Donald Trump’s new executive order on Venezuelan oil revenue is meant to ensure that the money remains protected from being used in judicial proceedings.

The executive order, made public on Saturday, says that if the funds were to be seized for such use, it could “undermine critical U.S. efforts to ensure economic and political stability in Venezuela.”

The order comes amid caution from top oil company executives that the tumult and instability in Venezuela could make the country less attractive for private investment and rebuilding.

“If we look at the commercial constructs and frameworks in place today in Venezuela, today it’s uninvestable,” said Darren Woods, CEO of ExxonMobil, the largest U.S. oil company, during a meeting convened by Trump with oil executives on Friday.

During the session, Trump tried to assuage the concerns of the oil companies and said the executives would be dealing directly with the U.S., rather than the Venezuelan government.

Venezuela has a history of state asset seizures, ongoing U.S. sanctions and decades of political uncertainty.

Getting U.S. oil companies to invest in Venezuela and help rebuild the country’s infrastructure is a top priority of the Trump administration after the dramatic capture of now-deposed leader Nicolás Maduro.

The White House is framing the effort to “run” Venezuela in economic terms, and Trump has seized tankers carrying Venezuelan oil, has said the U.S. is taking over the sales of 30 million to 50 million barrels of previously sanctioned Venezuelan crude, and plans to control sales worldwide indefinitely.

“I love the Venezuelan people, and am already making Venezuela rich and safe again,” Trump, who is currently in southern Florida, wrote on his social media site on Saturday. “Congratulations and thank you to all of those people who are making this possible!!!”

The order says the oil revenue is property of Venezuela that is being held by the United States for “governmental and diplomatic purposes” and not subject to private claims.

Its legal underpinnings are the National Emergencies Act and the International Emergency Economic Powers Act. Trump, in the order, says the possibility that the oil revenues could be caught up in judicial proceedings constitutes an “unusual and extraordinary threat” to the U.S.



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As U.S. debt soars past $38 trillion, corporate bond flood is a growing threat to Treasury supply

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As the Treasury Department looks to ensure investors continue absorbing the fresh supply of debt it must sell, growing competition from companies issuing their own bonds could send rates higher, according to Apollo Chief Economist Torsten Slok.

In a note on Saturday, he pointed out that Wall Street estimates for the volume of investment grade debt that’s on the way this year reach as high as $2.25 trillion.

That’s as the AI boom increasingly sends companies, including hyperscalers and adjacent firms, to the bond market to fund massive investments in data centers and other infrastructure.

“The significant increase in hyperscaler issuance raises questions about who will be the marginal buyer of IG paper,” Slok said. “Will it come from Treasury purchases and hence put upward pressure on the level of rates? Or might it come from mortgage purchases, putting upward pressure on mortgage spreads?”

With U.S. debt topping $38 trillion, the federal government has already borrowed $601 billion in the first three months of the 2026 fiscal year, which began in October 2025, according to the latest data from the Congressional Budget Office.

That’s $110 billion less than the deficit during the same period a year earlier as tariffs helped revenue outpace spending. But the Supreme Court could strike down President Donald Trump’s global tariffs soon, and this year’s tax season should see a surge of refunds to account for new tax cuts under the One Big Beautiful Bill Act.

Meanwhile, Trump has vowed to boost defense spending to $1.5 trillion a year from $1 trillion, threatening to further deepen federal budget deficits.

And despite the Federal Reserve’s series of rate cuts this past autumn, Treasury yields remain about where they were in early September, suggesting the government will not see much relief on debt-servicing costs that are also contributing to the overall tally of red ink.

“The bottom line is that the volume of fixed-income products coming to market this year is significant and is likely to put upward pressure on rates and credit spreads as we go through 2026,” Slok said.

Apollo

To make sure there’s sufficient demand among bond investors, Treasury yields must remain attractive relative to the competition. Failure to draw enough investors raises the risk of so-called fiscal dominance, or when a central bank must step into to finance widening deficits.

That’s what former Treasury Secretary Janet Yellen warned of last weekend, during a panel hosted by the American Economic Association.

“The preconditions for fiscal dominance are clearly strengthening,” she said, noting debt is on a steep upward trajectory toward 150% of GDP over the next three decades.

At the same time, he holders of U.S. debt have shifted drastically over the past decade, tilting more toward profit-driven private investors and away from foreign governments that are less sensitive to prices.

That threatens to turn the U.S. financial system more fragile in times of market stress, according to Geng Ngarmboonanant, a managing director at JPMorgan and former deputy chief of staff to Yellen during her tenure at Treasury.

Foreign governments accounted for more than 40% of Treasury bond holdings in the early 2010s, up from just over 10% in the mid-1990s, he wrote in a New York Times op-ed last month. This reliable bloc of investors allowed the U.S. to borrow vast sums at artificially low rates.

“Those easy times are over,” he warned. “Foreign governments now make up less than 15% of the overall Treasury market.”



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ICE shooting that killed Renee Good sets up budget standoff ahead of shutdown deadline

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The killing of Renee Good by an Immigration and Customs Enforcement agent in Minnesota has sparked a potential funding battle just as the federal government faces another shutdown deadline on Jan. 30.

Democrats in Congress are considering ways to rein in President Donald Trump’s immigration crackdown after the fatal shooting, and legislation to fund the Department of Homeland Security could be one vehicle for it.

Sen. Chris Murphy, the ranking Democrat on the subcommittee that oversees the DHS budget, plans to introduce legislation that would require agents to have warrants for arrests, ban them from wearing masks during enforcement operations, limit the use of guns by ICE during civil actions, and restrict the Border Patrol to the border.

He is trying to gather enough Democrats who will demand guardrails on DHS in exchange for their votes to pass a spending bill for the department, sources told Axios.

“Democrats cannot vote for a DHS budget that doesn’t restrain the growing lawlessness of this agency,” Murphy said in a post on X on Wednesday.

At least one Republican, Sen. Sen. Lisa Murkowski from Alaska, has called for policy changes, saying the shooting in Minnesota “was devastating, and cannot happen again.”

“The videos I’ve seen from Minneapolis yesterday are deeply disturbing,” she said in a statement. “As we mourn this loss of life, we need a thorough and objective investigation into how and why this happened.”

Some Democrats in the House, where Republicans hold a razor-thin majority that has gotten narrower, have also said legislation for DHS appropriations should be used as leverage.

And Rep. Adriano Espaillat, a member of the House Appropriations Committee, suggested at a news conference Friday that Democrats should take an even more aggressive stance.

“I was of the belief that perhaps we could reform ICE. Now I am of the belief that it has to be dismantled as an entity,” he said. “This unaccounted for violence is part of its culture. And so we must dismantle it and build it from the ground up again.”

But after the longest government shutdown ever last fall took a heavy toll on the economy and social services, top Democrats like Senate Minority Leader Chuck Schumer have signaled they want to avoid another one a few months later.

Still, House Speaker Mike Johnson admitted on Friday he’s concerned Democrats’ targeting of immigration enforcement funding could interfere with overall negotiations on government appropriations.

“We should not be limiting funding for Homeland Security at a dangerous time,” Johnson said, according to Politico. “We need officials to allow law enforcement to do their job. Immigration and Customs Enforcement is a critically important function of the government. It is a top concern for Americans, as demonstrated by the last election cycle.”



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