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The hardest interview question you'll ever have to answer

Grid hangs out with Chicago’s top headhunters and in-house recruiters to learn what it takes to ace the interview at companies like LinkedIn, Dyson and Edelman. This week, she sits down with Punchkick Interactive.

Punchkick Interactive co-founders Ryan Unger and Zak Dabbas speak of the culture at their mobile marketing company with the reverence of true believers. The underlying principle is total candor — no politics, no bureaucracy, no secrets. They post every number except for individual salaries, and each hire has to be approved by everyone who’ll work with the individual. Even firings are done to some extent by consensus.

That means they take their time finding people who can thrive in an unusual work environment. The interview process for a given position takes upwards of eight hours. “The number one thing that can destroy our business is hiring the wrong people,” says Dabbas. For now, Punchkick seems to be doing okay. The seven-year-old firm counts 15 of the Fortune 100 as clients.

On fire

Think of the hardest question you’ve ever had to answer in an interview. K, got it? Now try coming up with a response to this:

“What was the last time you should have been fired?”

When Unger springs that on candidates, he’s actually looking for an answer. “Whatever the worst thing that you think you’ve ever done, that’s what you should be saying,” Unger says. Unger and Dabbas are ruthless about maintaining a culture of transparency at Punchkick — an ethic they’ve practiced ever since Dabbas took the rheumy-eyed Unger to get evaluated for narcolepsy in college (he tested positive). To that end, this doozy of a question is simply the most efficient way they can test a candidate’s tolerance for radical honesty. “I just care if you tell me, ‘Oh I don’t know, I’ve been pretty good, I should have probably never been fired.” Wrong answer. “It’s a test of authenticity.”

Don’t get scattered

Just like Addison Group’s Tom Moran, who likes to see candidate’s wallets, Dabbas and Unger look for ways to get candidates off message. Sometimes, that means pulling out a game of Scattergories in the middle of an interview. “What we’re trying to do is kind of simulate what it’s really going to be like here,” Dabbas says. “There’s going to be interruptions, there’s going to be people always walking in, and we’re looking for folks who can take it in stride.” When candidates freeze up, Dabbas says it’s clear they’re not meant to work at Punchkick. “I think that in the long run we’re doing them a service. Because if a game of Scattergories could make you seize up, you’re not going to last long here.”

Don’t suit up

Sometimes, looking the part means dressing down. “It definitely is like a red flag for [a candidate] to wear a suit because it means you don’t quite know the culture,” Unger says. Punchkick’s first interview is all about culture and getting to know candidates, and usually takes place in the game room. Dabbas and Unger are looking for candidates who have done enough research to know it’s not a suit and tie kind of office. “If you look us up at all online, if you look at our blog and you look at some of the posts, there is no way you should come in here in a suit,” Dabbas says. “There’s just no way.”

But keep it professional

Even though the environment and the attire are relaxed, Dabbas and Unger say professionalism has its place. On their long list of absolute taboos: cussing, tardiness, and bringing food into the interview. “There’s so many things that people do that just, they eliminate themselves,” Dabbas says. At Punchkick, nearly every employee sits with clients, so how candidates behave in the interview is important. “If this is what you do with us, what happens with clients around?” Dabbas asks.

Instant CEO

Unger likes to ask, “If you were CEO for the day and you had absolutely no consequences, what would you change about it?” Putting chocolate milk in the water coolers is all well and good, but if a candidate complained about their job earlier in the interview and then doesn’t address it in the hypothetical, Unger gets concerned. “If you just sat here and told me that you have a pretty terrible developer workflow and that’s not what you’re focused on, that’s a huge red flag,” he says.

ABOVE: Zak Dabbas and Ryan Unger (l to r)