Leadership, Startup Advice

Attitude over ability: Twitter and Square founder Jack Dorsey reveals how he hires for success

Stephanie Palmer-Derrien /

Jack Dorsey

Twitter and Square founder and chief Jack Dorsey.

Having founded social media leviathan Twitter and then $US26 billion payments fintech Square, Jack Dorsey knows a thing or two about building a business. And for him, success comes from great culture and great people. Let’s be real. He would know.

The famed Twitter founder and chief founded Square in 2009, in a bid to make credit card payments more accessible to small businesses. The startup listed on the New York Stock Exchange in 2013, and now has a market cap of $US26 billion ($38.25 billion).

At a Fintech Australia breakfast event in Melbourne, where he announced the launch of the new Square Terminal product in Australia, Dorsey said one of the most important lessons he learnt from Twitter was how to hire.

Speaking to Shahirah Gardiner, founder and chief of Aussie fintech Finch, he said when it comes to startup success, “it all comes down to — and you all know this — who you hire and who you bring on the team”.

Hire for purpose

First, Dorsey said something he learnt from his experience founding and growing Twitter was that hiring a great team was less about getting “the superstars” and more about achieving the right dynamic in the team.

You can have the best engineers, product people or designers, he said, “but, they could be super negative or super toxic, and that brings the whole company down”.

When building the team for Square, he drew on his prior experience.

“I really focused a lot of my time and attention on finding people who would contribute to a team that was healthy, that was inspiring, that was challenging, that raised the bar on what we thought was possible,” he said.

To achieve this, he asked prospective employees a simple question: why Square?

Some people would focus on the innovation, saying they wanted to be part of the “rocket ship” business that was about to take off.

For Dorsey, “that is exactly the wrong answer”.

What he was looking for was something more personal. For example, if someone had a family member who owned a small business, and was not able to take credit cards.

In an ideal world, that person would want to be part of the solution. They would also be able to identify things the business was doing wrong, and explain how they would contribute to fixing them.

Square would be looking for “someone who is already engaged in solving the problems and, more importantly, is aligned with the purpose of the company,” Dorsey said.

Find risk-takers

Dorsey also said he likes to test how ambitious and how risk-averse prospective employees may be, particularly in the early days of Square.

The startup was entering an industry that is traditionally “pretty conservative and pretty risk-averse”, he said, adding that it “tends to say ‘no’ a lot”.

The founder recalled a warning he gave to “at least” Square’s first 50 employees.

“I would say: ‘This company will either be a massive success, or I’m going to jail. There’s nothing in between.’”

The startup was entering a highly regulated space, and would have to question some of those regulations. Early employees had to have an appetite for risk.

And, just to add to the uncertainty, “it wasn’t until employee 60 or 70 that we hired someone with any financial experience”, Dorsey said.

“We could be very naive, but being naive allowed us to question some of the fundamentals … that really pushed us.”

Square was looking for people who “were brave enough to ask the question ‘why’”, and who were “strong enough to arrive at the answer ‘I don’t know’”, the founder explained.

Take your hands off the wheel

As chief executive of both Square and Twitter, Dorsey said he is often asked how he manages both roles, and both businesses. For him, however, it’s about letting go of control.

“I don’t want to keep myself in the driving seat, necessarily,” he said.

“I don’t want to build a company that’s dependent on any one person, including myself.”

Dorsey wants any company he builds to last beyond himself, and beyond any one employee. And realising this has made him think about his own position differently.

“My number one job is to make sure we have an amazing team dynamic,” he said.

“If we don’t have that, we’re not going to be able to do anything at all.”

That dynamic should be self-sustaining and autonomous, he added, and “contributing in a healthy way to itself”.

Leaders should be able to step back, and not be involved with every single decision.

“If you have to make every decision as a CEO or as a leader … you have built a failure of a company, and one that will naturally fail when you take your attention off of it,” he explained.

That’s neither scalable nor empowering to employees.

“You’re not going to hire great people if you’re making every single decision.”

Dorsey doesn’t feel decision-making should be his job. And if it is, that means there is “an organisational failure”, he said.

His job is “to raise the bar on what we thought was possible”, reminding people they have already made the impossible possible, and empowering them to do more.

“As we strive to do so much more, everyone’s skill increases within the company,” he said.

“My role is mainly a check on the company and the organisation and this organism that we’re all building together, to make sure we’re serving our customers, and we’re being creative, and we’re pushing ourselves to be one per cent better every single day.”

If a leader is involved in every single decision, not only does it lead to a less empowering office environment, it can also be a detriment to innovation.

“I just don’t think that’s scalable, I don’t think that’s healthy, and I don’t think it’s going to lead to true invention,” Dorsey said.

“True invention doesn’t happen in a single person’s head.”

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Stephanie Palmer-Derrien

Stephanie Palmer-Derrien is the editor at StartupSmart. You can contact her at [email protected].