From high school dropout to founder of Twitter and Square, Jack Dorsey’s career path has been a wild ride. Along the way, he’s developed a unique management style. While his tactics may seem unconventional, they’ve helped him develop some of the most desirable–and effective–corporate cultures in Silicon Valley.

1. Be a leader, not a decider.

For Dorsey, a good leader is someone who guides the people in their organization so that they can make the big decisions–not someone who issues decisions down from on high. "If I have to make a decision," he says, "we have an organizational failure." With this kind of perspective, the health of an organization depends not on the power of its leader, but on the power of its members.

2. Empower employees–and hold them accountable.

In 2014, Dorsey published an email that he’d sent to the staffers at Square, admonishing them for name-dropping him in order to get their projects and ideas approved. "If you have to use someone else's name or authority to get a point across," he wrote, "there is little merit to the point (you might not believe it yourself). If you believe in something to be correct, focus on showing your work to prove it." This approach both empowers employees to be creative and innovative in their thinking--and also puts the onus on them to produce quality work, that deserves to be taken seriously.

3. Admit your weaknesses--and then overcome them.

When he launched Square, Dorsey knew that people were just waiting for the venture to fail. So he tackled their doubts head-on. In an infamously audacious move, he presented investors with a list of 140 reasons why Square would fail--along with his own rebuttals. The gambit worked: investors came on board, and now Square is the leader in the mobile payment industry. With that initial list, Dorsey proved that he knew the industry, he knew the field, and he knew the limitations and potential of his idea. What lesson can entrepreneurs take from this? Be creative, be daring, and always show people that you know exactly how to overcome your weaknesses.

4. Foster transparency.

At Twitter and Square, Dorsey gave employees unprecedented access to company strategy. At Twitter, notes from engineering meetings are shared company-wide. At Square, employees get access to documents from board of director meetings, and get to ask questions and give feedback. This kind of inclusivity and transparency makes people feel like they’re working towards common goals.

5. Test everything, then test it again.

For Dorsey, perfecting the product is key--and he’s developed unique ways of testing it. The Square offices house a coffee shop that serves a proving ground for Square’s hardware and software. And Square employees work shifts in local coffee shops so that they can see how their services work in the field. This focus on usability means that Dorsey’s clients walk away satisfied. And their satisfaction equals his success.

Published on: Sep 2, 2015
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