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Mark Cuban credits his first tech job to an interview strategy: I answered a trick question honestly

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Forty years ago, Mark Cuban wasn’t sitting courtside at Dallas Mavericks basketball games or fielding pitches on ABC’s “Shark Tank” — he was sharing a three-bedroom apartment with five roommates.

Then, he landed his first job in tech as a PC software salesperson at a company called Your Business Software. But in an old blog post, which Cuban recently shared on Twitter, the billionaire revealed he almost didn’t land the consequential role. He had no experience and was “trying to pull out every interview trick I knew.”

The interviewers weren’t impressed, Cuban wrote, until he answered one question: “What do you do if a customer has a question about a software package and you don’t know the answer?”

As Cuban recounted, there was a long pause. “After who knows how long, I blurted out that, ‘I would look it up in the manual and find the answer for them,'” Cuban wrote. “Ding ding ding… [the interviewer] just loved the answer.”

The question was designed to gauge a job candidate’s confidence level — to see if they’d freeze, refuse to admit they didn’t know something, or swallow their pride and seek out an answer right in front of a customer. Cuban didn’t know it was a trick question, so he answered it honestly, stumbling into the correct answer.

The foot in the tech industry’s door was all Cuban needed: Less than a decade later, in 1990, he created then sold systems integration computer company MicroSolutions for $6 million. His next business, internet radio company Broadcast.com, was acquired by Yahoo in 1999 for $5.7 billion in stock.

Cuban bought a majority stake in the Dallas Mavericks for $285 million for a majority stake the following year, he tells CNBC Make It.

Ironically, Cuban says the best entrepreneurs often lie to themselves, at least a little bit. “Behind the lie are the ‘wantrepreneurs,'” he said at a Dallas Startup Week event in 2019. “The people who talk about doing it, but don’t take that step. And then you lie to yourself a little bit and you say, ‘I can do this.’ You’re scared s—less, but you know you can do this. You take one small step.”

You just can’t lie to the people around you — especially in job interviews. In 2019, a joint report from U.S. careers advice site TopInterview and job search platform Resume-Library found honesty was one of five most desirable personality traits in employees.

Cuban’s fellow “Shark Tank” star Kevin O’Leary feels similarly. In May, O’Leary told CNBC Make It that his top piece of advice for job applicants was to tell the truth.

“Great HR managers have an innate skill to sense bull—-,” he said. “They know when you’re lying to them, because [detecting that is] what they do 24/7.”

This story has been updated to reflect that Cuban bought a majority stake in the Dallas Mavericks for $285 million in 2000.

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