Billionaire Jay Chaudhry has built multiple companies.
His first was SecureIT in 1996, which was sold for $70 million in an all-stock deal two years later. That was followed by AirDefense, CipherTrust and CoreHarbor in the earlier 2000s, all of which were ultimately acquired. He founded his most recent company, Zscaler, in 2008, and is currently serving as its CEO. Zscaler has a market cap of $26 billion as of Monday.
With so many companies founded, Chaudhry has done his fair share of hiring. Depending on what kind of role he’s looking for, he often separates candidates into two categories: builders and operators. Builders thrive in a chaotic startup environment while operators prefer a structured, larger company.
He also pays attention to turn-offs in candidates. Here are two of his biggest red flags.
One thing Chaudhry pays attention to is how interviewees measure success. “People who just focus on building fiefdoms” don’t cut it, he says.
These are people who put an emphasis on the specific resources that they have. “They view the success as linked to the budget and number of people who report” to them, he says. It’s a type of rigidity that he believes doesn’t lend itself to the creativity needed in business. If a candidate comes in asking about how big their team or budget will be, he knows they’re not focused on the right measures.
Instead, Chaudhry is interested in hiring people who know that “it’s the growth that’s very, very important,” he says. They’ll take whatever resources they have and make something out of them.
The second thing Chaudhry pays attention to is “people who like to package their results to look good,” he says.
Early in his career, he worked at large tech companies like IBM and Unisys. And right before business reviews, he’d see leadership “busy for two, three weeks packaging their PowerPoint slides to make the results look better and better,” he says.
“And I would think, wow, these people should be out there meeting with customers and making a difference” instead of spending their time on PowerPoints, he says. What makes a company great is people who know “we need to keep on looking for areas of improvement,” instead of trying to make existing results look better.
When he’s interviewing people, he looks for an indication that they want to fix problems. “I tell them that at Zscaler, we spend 10% of the time of a meeting patting ourselves on the back,” he says, then 90% of the time “looking for areas of improvement.”
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