Why Twitter founder Jack Dorsey had to fire a “superstar” employee

An employee’s attitude and the culture they bring is much more important than their individual skills, Twitter and Square founder and CEO Jack Dorsey says.

Speaking at a Square event in Melbourne earlier this week, Dorsey discussed how he has always put company culture above all else, even if this means having to let a “superstar” employee go.

“One of the things I learnt early, early on in Twitter is sometimes you have these people who are just superstars – they have all the right answers, they have all the skills and they’re amazing,” Dorsey says.

“But they’re negative – they’re super, super negative.”

No matter how talented an employee is, if they don’t fit in with the company culture and provide a positive influence then it’s not going to work out, he says.

“You tend to optimise for skills rather than recognising that the negative is actually dragging everything down,” Dorsey says.

“As you look at your team, if there’s anyone who’s negative on the team you realise everything is going to become harder because of that negativity. No matter how good this person is, if they can’t bring a positive and optimistic attitude to their work you’re probably going to be slowed down.”

Letting go of a “superstar” employee because of this in the early days of Twitter was one of the most difficult things Dorsey had to do, but he says it also led him to an important realisation.

“That was really hard for me because we did have people that were just amazingly skilled, brilliant people but ultimately they were just super negative,” he says.

“I was so resistant to recognising that and parting ways but once I did all this new leadership emerged and all this new positive energy emerged. It just unlocked all these interesting attributes in other people.

“When you’re three people you have to make these moves. It’s super, super difficult but it’s the right thing to do in service of your purpose and your customers.”

It’s when you get this startup culture just right that true innovation will emerge, Dorsey says.

“The team you build is so critical and when you want to grow you have to do it with others, you can’t just do it alone,” he says.

“The relationship and structure you build is really messy, chaotic and noisy but at the same time it’s really beautiful.

“That’s where true creation, invention and innovation comes from – from all the contrasts you provide one another to get the truth, to figure out what you’re actually trying to do and why.”

During the Square Talk Shop event at Federation Square, Dorsey also provided a number of important lessons and takeaways for founders and entrepreneurs, from the early days of Twitter to the global success of Square.

You need to be constantly learning

Despite being the founder and CEO of two globally renown tech companies, Dorsey says he is still constantly learning, something that has been driving his journey from the very beginning.

“I never wanted to be an engineer when I was a kid, but my parents got a computer and I knew I could do something interesting with it,” he says.

“So I had to learn everything about it. I learned the bare minimum to start drawing on it and I learned a little bit more and a little bit more.

“My whole life has pretty much been like that.”

This process was very similar to when Dorsey, Ev Williams and Biz Stone were building on the initial idea for Twitter.

“It was just something we wanted to use and we learned everything we needed to build it, then it turned out we had a business,” Dorsey says.

“I had to learn how to be a CEO, how to hire people, how to build a team and how to raise money.

“That was our approach with Square as well. We knew nothing about the financial industry, about credit cards or about banking. But we learned everything necessary to do it.”

Going all in

When Dorsey and his co-founders started Square, they took a very big risk.

“We started Square when I was in credit card debit and we put the whole company on our two credit cards,” he says.

“We took a significant financial risk on a bet that this would eventually work out.”

And this willingness to take risks still permeates through Twitter and Square, he says.

“What I’m proud of is that when we did get to proof of concept and we did show people, we kept taking risks,” Dorsey says.

“You have to believe in what you’re trying to do and others will start believing as well. A lot of those times we thought, ‘oh my god, this is all going to fail’, but we persevered and had the grit to keep going and figure it out.”

The virtues of Twitter for businesses

When launching Square, Dorsey says he was able to draw on his other startup for assistance.

“We used Twitter as a broadcast channel to communicate that we exist, we used it to announce new features and we used it to recruit people,” he says.

“It’s much easier starting a company with it now than without it.”

He says the most useful aspect of Twitter for business owners is the near-instant feedback it providers from users and customers.

“The feedback that you get instantly is amazing,” Dorsey says.

“I like seeing both the positive and the negative. If you see both then you find the truth, and the truth will get you to the right answer.

“We can tell what our customers are doing, what they like and what they don’t like, and we can do that instantly. That helps you make better decisions in the moment and if you make better decisions you can grow faster.

“We discover so much just from watching.”

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