Dorsey championed the mobile payments company as an “analytics” company, allowing store owners to query things like “total # of biscotti sold” versus the complete lack of data and analysis involved in many outmoded traditional point-of-sale systems.
Dorsey emphasized that this bent towards analytics and transparency was also endemic to the culture at Square, which is perhaps the most “designed” startup culture of all startup cultures.
Dorsey brought up the infamous meetings conundrum, raised in Maker’s Schedule, Manager’s Schedule, that sometimes managers can get so bogged down in planning meetings about work that they forget about actual work. This is somewhat of an epidemic at Aol-era TechCrunch, and in most big companies. And when this happens, people “start thinking of things that are not actually the work,” says Dorsey, who is determined to run Square differently.
Dorsey prevents this “secret meeting” problem not only by making the physical environment of Square transparent, with few conference rooms and lots of space, but by making every meeting with more than two employees require note-taking, which then gets shared with the rest of the 600 person company. In addition, the Square board meeting deck is also shared with the whole company at its monthly board meetings. Impressively no Square board decks have leaked to TechCrunch, yet.
“We benefit so much from how quickly we can move in changing circumstance,” said Dorsey, the envy of legacy incumbents which have endless over-management and speed bump bureaucracy. “It’s very hard to keep secrets at Square,” he said. Except when those secrets are about Twitter, I guess.*
* While GigaOm founder Om Malik and Dorsey did not talk tweets during the interview, Square Communications Head Aaron Zamost tells me Malik was only asked explicitly to refrain from talking about the Cardinals losing in the World Series.