Jack Dorsey Leadership Style

Jack Dorsey Leadership Style: Lots of people set out to change the world, but Jack Dorsey is one of the few who actually succeeded. He had an idea, and he turned that into one of the most popular and far-reaching methods of communication ever to exist. 

Twitter is so deeply integrated into the 21st century lifestyle that politicians and business leaders use the platform to announce policy. Companies connect with consumers, and users create and maintain relationships with like-minded strangers located in all corners of the globe.

Twitter (TWTR) hosts 330 million active users every month, and 145 million of those access the social media site daily. Together, they post more than 500 million messages every day. 

Some leaders might have been satisfied with the creation of a single $43 billion-dollar company, but Dorsey doesn’t rest on past success.

In 2009, Dorsey launched Square (SQ) – a brand-new method of making and receiving digital payments. Dorsey said, “Twitter is about moving words. Square is about moving money.”

Given that Square has a current market cap that flirts with the $100 billion mark, it is clear that Dorsey is a world leader in innovation and creation of simple solutions to complex problems. 

Of course, no one can build a multi-billion dollar company alone. Jack Dorsey’s leadership style is key to his ability to transform ideas into real-world services. That has entrepreneurs asking: what is it about Jack Dorsey’s leadership style that sets him apart? 

What Type of Leader Is Jack Dorsey?

It’s true that Jack Dorsey sparked the social media flame, but he is the first to say that he didn’t do it alone.

Whether he is discussing Twitter (TWTR) or Square (SQ), Dorsey gives most of the credit to his team. Dorsey spends his time inspiring, motivating, and empowering his people, trusting that they have the skill and ability to do their jobs well.

One of the most important contributions he makes to his companies is getting out of the way so employees can get the job done.

Characteristics Of Jack Dorsey Leadership Style

The most common word used to describe characteristics of Jack Dorsey’s leadership style is bold.

Within that single syllable, you can find all of the qualities that made him a massive success. He is fearless, even when it means challenging the status quo, and he has never hesitated to introduce big ideas that fly directly in the face of traditional methods.

In fact, one of his most-often repeated quotes is “Expect the unexpected. And whenever possible, be the unexpected.” 

That bold, fearless confidence came through when he founded Twitter, and it was clear once again with Square. Dorsey made space for his team to transform communication and mobile payments, then stood back and let them build the future of both. 

Is Jack Dorsey a Laissez-Faire Leader?

Some have speculated that Jack Dorsey is a laissez-faire leader, because he doesn’t put too much emphasis on telling employees what to do and how to do it. However, nothing could be further from the truth.

A laissez-faire leader is one that basically checks out of the process, handing responsibility and authority to team members. Dorsey is committed and fully involved in his companies. 

Dorsey serves as a coach and mentor to team members, supporting them in getting the job done. While he expects them to do the “writing”, he is always present to “edit”.

Dorsey has found a balance between empowering his people and abandoning them to their own devices.

Is Jack Dorsey A Transformational Leader?

Some have said that Dorsey and his companies have been the biggest disruptors of our time. He took the microphone away from celebrities and the media, handing it over to average people who have something to say.

Thanks to Twitter, one-way communication is all but obsolete. Anyone can speak directly to fame, fortune, and power. 

Conversely, individuals with an interest in connecting and influencing large groups don’t have to wait to be “discovered” by movers and shakers. They can create their own platform and amplify their own voice through social media. 

That’s empowering – and that’s Dorsey’s goal.

He leads his companies in the very same way. Dorsey doesn’t stand on ceremony, observing strict hierarchical standards. He spends his time talking to people who don’t report to him, inviting and encouraging their ideas. That leads to more creative solutions, as he pointed out when he said: 

“I spend 90% of my time with people who don’t report to me, which also allows for serendipity, since I’m walking around the office all the time. You don’t have to schedule serendipity. It just happens.”

When you consider that transformational leadership is marked by inspiring, motivating, and empowering employees to discover innovative ways of doing things, it is clear that Jack Dorsey is a transformational leader.

Is Jack Dorsey A Servant Leader?

The foundation of servant leadership is people before power. It assumes that if you do what’s right for your employees, customers, and community, business success will follow naturally.

While he isn’t widely considered a servant leader, a closer look shows Jack Dorsey has more in common with this leadership style than not. 

Dorsey’s companies were both founded on making life easier for users by simplifying complex processes.

Dorsey has never shown signs of being after power – instead, he has made it clear that his passion is elevating others.

While Dorsey doesn’t blatantly exude servant leadership like some of his CEO peers – Cheryl Bachelder (Popeyes), Garry Ridge (WD-40), Melissa Reif (The Container Store), and Sylvia Metayer (Sodexo) come to mind – his on-going concern for the world beyond himself demonstrates that he has many qualities of a servant leader. 

Is Jack Dorsey A Visionary Leader?

His ability to see beyond what is to what is possible is just part of Jack Dorsey’s skillset – but it is this particular skill that makes him a visionary leader.

Dorsey thrives in chaos and knows how to maneuver through it to the other side. More importantly, he is capable of supporting his employees through times of transition, change, and disruption. 

He does this by holding fast to three basic tenets: first, he believes in transparency above all else. Sensitive information and business data is typically kept confidential from the rank-and-file, but Dorsey doesn’t operate that way.

He makes those details available, so there are no secrets about where the companies stand and where they are headed. This transparency builds trust – the second tenet. Dorsey makes trust a priority in his business relationships. 

Finally, Dorsey believes in serendipity. He knows that big ideas and opportunities can’t always be predicted or planned. He is open to seeing the possibility in the unexpected. More importantly, he is open to hearing from others when they see possibilities. 

Jack Dorsey Leadership Quotes

Jack Dorsey leadership quotes aren’t like those of traditional business tycoons. He doesn’t bother with platitudes or vague references to idealized concepts.

Dorsey is firm, confident, and real when he speaks about leadership, and he continuously emphasizes the importance of partnering with others. Examples of leadership quotes that made it into MBA case studies include: 

  • Great companies don’t just have one founding moment. They have many founding moments.
  • Everyone has an idea. It’s about executing the idea and attracting other people to help you with the idea.
  • Ideas that can change the course of the company can come from anywhere.
  • Success is never accidental.
  • It’s empowering to be asked to look at what’s possible, not told how to do it.

These quotes define who Jack Dorsey is: a leader who respects and values the many people who join forces to make a company great. 

Jack Dorsey Leadership Style Conclusion

Given his enormous success in not one but two billion-dollar businesses, it wouldn’t be a surprise if Jack Dorsey’s leadership style involved directing others to follow his instructions.

After all, he clearly has the creativity and vision to change deeply ingrained methods of getting things done, and he has proven again and again that he can achieve results where others failed. 

However, while he is certainly bold and confident, Dorsey remains committed to collaboration, teamwork, and empowering others.

Perhaps, on occasion, it would be easier to simply tell employees what to do, but Dorsey isn’t tempted. His leadership style is deeply rooted in being a transformative force that empowers his team to build a successful business. This is summed up in a 2017 remark he made: 

My goal is to make sure that we are building something that outlives me… I need to build structures that aren’t dependent entirely on me. That means I need to recognize leaders who can succeed me.

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