Jack Dorsey doesn’t know how to grade his performance. It’s early May, and Dorsey has just finished his annual reviews of Square’s 800 employees. He now needs to complete his own. So the Square CEO sends out a Google Doc to the entire company soliciting feedback, but he makes two suggestions that border on the masochistic: All comments should be anonymous, and all comments should be visible to everyone inside the company. “Write whatever you want,” Dorsey tells his troops, adding that he wants to learn “where I’ve done well, where I’ve done poorly, and where I’ve completely screwed things up.”
When we meet for a walk on a gray morning in San Francisco several weeks later, Dorsey is in great spirits. He jokes about overly cautious Californians who refuse to jaywalk; and in the elevator when we bump into two police officers leaving Square headquarters, Dorsey greets them with a smile and a handshake befitting a small-town mayor. He tells me he hasn’t read through all the feedback yet from his Square colleagues–he received more than 500 responses–and will only hint that much of it stressed the need for more “focus” at the company. He’s being intentionally vague, of course. When I ask what grade he’ll give himself in the self-assessment he’s writing, Dorsey tersely replies, “Not an F.”
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