Can a single question reveal whether someone's a perfect fit for your office — or a walking culture clash waiting to happen?
It seems unlikely. Culture is fuzzy at best, with most companies struggling to define theirs without descending into corporate mumbo jumbo.
Still, when I asked a dozen founders and executives what they ask to dodge hiring disasters, each had a go-to question. Some were smart. A few were strange. One or two were bizarre.
The stakes are high. "If you don't have product-market fit or you charge customers the wrong amount, those are things you can fix," says Steve Hunter, founder and CEO of London-New York-based AI company 9fin. "Fixing the culture is incredibly difficult."
So what are leaders actually asking?
Mark Stokes, CEO of UK spacetech Magdrive, asks candidates whether they play the cult-classic game Dungeons & Dragons. A "yes" is a good sign here (though it could prove a red flag among a handful of companies I know).
Michelle Volberg, founder and CEO of recruitment platform Twill, advises founders to ask: "What's your go-to karaoke song?" I'm guessing I Will Survive by Gloria Gaynor is a good answer and Creep by Radiohead is a bad answer.
Others aim for insights on candidates’ moral reasoning. Natalia Edde, chief operating officer at Mindset Consulting, a Spanish PR agency working with tech companies and VC funds, probes applicants on subjects seemingly unrelated to the job description, such as their views on euthanasia.
"Our intention is not to judge the person's opinion itself but to understand how someone reasons through morally complex topics. Their empathy, nuance and ability to disagree without becoming dogmatic.”
She also has a tamer litmus test: PowerPoint or Excel? "That question alone says a lot about how someone thinks," she says.
‘Psychological alignment’
Some approaches are more controversial. Chris Spillane, a communications adviser turned stealth founder, recalls a legaltech startup that sent new hires to meet a psychologist to assess "alignment with the founder's personality". Another company asked candidates how important money was to them to weed out those unmotivated by the company mission.
"Less controversially, VCs often invite new hires to meet them in person and spend days chatting about work and life to see if they're a good fit. Sensible, if potentially slow," he says.
Then there are the blindingly obvious questions that still trip candidates up. Chris Sisserian, head of platform at Manta Ray Ventures, says two of the most effective screens are simply: 'What do we do?' and 'Why do you want to work here?'
"Bizarrely, 90% of people can't answer them," he says.
The pizza test
Filip Kirschner, founder and chief operating officer of Czech software company Applifting, uses the "pizza test".
Imagine it's Saturday night and your product has suffered a major security breach. You work all night with the team and save the day. Come morning, do you go straight home or go for pizza together? Those who choose pizza, he argues, are the people you want in a crisis.
Hunter at 9fin asks candidates why they want this job specifically — and what they'd say if another company offered more money.
One of his bluntest questions? If an offer were made immediately, could they accept it? "If the person says, 'Oh well I've got one or two other interviews lined up, can I tell you later?' That's a red flag. You don't want to be anyone's second choice."
Perhaps the hardest question to answer comes from Bianca Zwart, chief strategy officer at Dutch neobank Bunq, which received 20k applications a month last year.
Every interview ends the same way: "Tell me why you're not a fit for this role." Senior candidates, she notes, often find it hardest to answer.
Others, of course, might say that culture-fit screening is hokum. Yoram Wijngaarde, CEO/founder of Dutch data platform Dealroom, says he tries to have “a frank conversation” with would-be hires before “listening very much to my gut.”
Similarly, Stef van Grieken, CEO of Swiss-Dutch AI drug discovery company Cradle, says he doesn't have a go-to question. His reasoning goes against popular sentiment: he doesn't want a team of like-minded people.
"You run the risk of becoming a monoculture," he says.
