After leading 4,000 job interviews, here’s what Smartsheet’s co-founder loves to ask candidates

Smartsheet co-founder and TerraClear CEO Brent Frei chats with CoMotion Executive Director Vikram Jandhyala at the UW last week. (GeekWire photo / Taylor Soper)

As a veteran tech entrepreneur and co-founder of companies like Onyx Software and Smartsheet, Brent Frei has conducted more than 4,000 interviews. Over that time he’s figured out the type of questions to ask that help him figure out who to hire — and it has little to do with a specific discipline or technical skills.

Frei paid a visit to the University of Washington’s CoMotion Innovation Center last week for a fireside chat with CoMotion Executive Director Vikram Jandhyala. The conversation focused on lessons from Frei’s experience starting two software companies that went public — Onyx in 1999; Smartsheet this past April — and his current adventure leading high-tech rock-picking startup TerraClear.

When it comes to assessing potential employees, Frei likes to dig into the candidate’s character, asking them to talk about their values. He’ll then figure out what motivates the person to go to work and why they’ve picked that particular company. He’s also interested in what culture they’d create if given the opportunity.

“Then I ask something like, ‘what are you most proud of?” Frei explained. “If you tell me that you’re proud of your friends and family, that’s a perfect answer for me. A lot of people pick something like, ‘I coded this algorithm’ — really? That’s what you’re most proud of? I don’t think I’d put that on my tombstone. You get a sense for who they are, and most people are consistent across their lives.”

Frei said it’s important to find people that are “coming to you for the right reasons.”

“They are smart and ambitious — not just for themselves, but for the whole team,” Frei said. “I can pick those people out pretty quickly.”

Life on the farm: Brent Frei and his team are based in Bellevue, Wash., but they’re using his Idaho family farm as a testbed for TerraClear. (Photo courtesy of Brent Frei)

Frei and his leadership team at Onyx, a CRM software maker that launched in 1994 out of Bellevue, Wash., certainly made some good hiring decisions. Frei said 18 former Onyx employees went on to become CEOs of other companies.

Frei is also a big believer in entrepreneurs and employees who don’t quit. Onyx went through a difficult time after the dot-com bubble, but persevered and was later acquired in 2006. Smartsheet nearly ran out of money in its early days and Frei almost sold his house. But the company, which helps Fortune 500 customers manage and automate key work processes, implemented key design changes that ultimately helped propel Smartsheet to big growth and an eventual IPO.

Frei likes to ask interviewees about an “impossible chasm or immovable object” in their career.

“Most people will say it’s never happened to me — that’s BS,” Frei said. “It’s happened to almost everybody.”

Frei said having the grit to overcome obstacles and plow through situations is the “difference between great and average or crappy employees.”

“You figure out a way,” he said. “If you’re an entrepreneur, that is absolutely essential.”

Frei recalled playing a college football game at Dartmouth as a defensive end. He tried to sack the quarterback, but an offensive lineman kept tackling him — a clear penalty, but the referee didn’t throw a flag.

Frei’s coach lit into him on the sidelines, demanding that he work harder. Frei tried to explain what happened with the opponent’s illegal move.

“Well, OK, then we are going to lose,” the coach said.

That moment stuck with Frei for the rest of his life. Everyone has a valid excuse for why they can’t be successful — so what are you going to do to overcome what’s unfair, or what’s too difficult?

“It was real lesson in determination, effort, and never quitting,” Frei said.

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