4 Leadership lessons learned from Jack Dorsey’s most recent resignation letter


“Jack Dorsey, painted portrait DDC_8826” by Abode of Chaos is licensed under CC BY 2.0


For the 2nd time since its founding, Jack Dorsey is stepping down as CEO of Twitter.


Dorsey co-founded Twitter in 2006, became its CEO in 2007, and was forced to step down in 2008. In response to a weak post-IPO stock price, Dorsey returned as CEO in 2015.


Dorsey posted the news of his departure on — where else? — Twitter, along with the email he sent out to employees.


Jack Dorsey's time in tech has been nothing less than polarizing. But love him or hate him, he helped create two of the biggest tech companies in the world (Twitter and Square). You don’t have to agree with the guy, but there are some valuable leadership lessons in his most recent resignation letter:


Leadership Lesson #1 ~ Know when you’re hurting the business

“ There’s a lot of talk about the importance of a company being founder-led. Ultimately I believe that’s severely limiting and a single point of failure. ”

Dorsey does not mince words when he says that “being founder-led” is a “single point of failure.” Does the founder limit the business?


What would Facebook (I mean Meta) look like without Mark Zuckerberg?


What will Amazon look like 10 years from now without Jeff Bezos at the helm?


Will Tesla fall into obscurity if Elon Musk ever leaves?


Every leader needs to figure out how to objectively look at their presence in the business to assess if they are helping or hindering.


Leadership Lesson #2 ~Promote from within

“ Parag has been behind every critical decision that has helped turn this company around. … Parag started here as an engineer … and now he’s CEO. ”

Faced with the reality of replacing a CEO, all companies must answer the same question: promote internally, or hire externally?


When a company wants to grow/change directions/revitalize/etc. there is always the temptation to bring in a “rock star CEO.”The hope is that they bring new perspectives without being constrained by the current culture. This would probably sense as Twitter has failed to keep up with its tech competition (i.e. TikTok).


But there can be some major advantages to promoting from within the ranks. First, there is potential for very little succession lag time. The new leader knows the company, is familiar with the politics and can hit the ground running. Secondly, it can be motivating to existing employees to know they also have a chance to make it to the top.


The board at Twitter obviously believes that promoting a 10-year veteran (Parag Agrawal) is the best choice.


Leadership Lesson #3 ~ Get out of the way

“ Parag is CEO starting today. ”

According to Dorsey’s letter, the switch of CEO’s was happening immediately. Even a non-business person would probably see value in an overlapping transitionary period, where the old guard trains their replacement. Not doing this will likely fuel rumours that Dorsey is not leaving willingly, but getting the outdoing boss out of the way can be beneficial for the new leader.


Later in his letter, Dorsey asks, “Why not stay or become chair?” Answering his own questions, he says, “I believe its’ really important to give Parag the space he needs to lead.” If the goal is to give Twitter moving in a new positive direction then ripping off the leadership band-aid makes a lot of sense.


Leadership Lesson #4 ~ Do what's best for the business

“ There aren’t many founders that choose their company over their own ego.”

Every founder sees their venture as their entrepreneurial baby. Just like a parent, it can be very difficult to “let go.” What if the company loses its way? What if they stray from my vision? What if the company doesn’t survive? This can be terrifying.


Dorsey obviously believes that he is holding Twitter back. By stepping down he is saying that the growth of the company is more important than holding on to his “baby.”


~~ Friends, thank you for reading!





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