A Beautiful Observation About The Start of Twitter

This is a true and unusual story about leadership and potential.

Coach Tony
Sep 7, 2016 · 2 min read

In 2005, I was an engineering manager for a 15-person startup.

One day, the CEO of the startup gave everyone in the company a very heady assignment. He asked us to take a few hours and jot down our best ideas for where we might take the company.

He asked everyone. And he demanded that we comply because everyone had to present their idea afterward.

There were basically six engineers and I was their boss. Two of those engineers were anarchists — they’d tell you that. They were really a huge problem to work with for big and for little reasons. One wouldn’t even stand up at the stand up meeting because he considered that too compliant.

The other three were intermittently challenging. One was threatening to punch their coworkers (it was a weird group).

The sixth was almost not worth talking to. He got his job done, never said no to an assignment, his code always worked. I basically only talked to him to award him a bonus and then a raise.

Going into this brainstorming session assigned by the CEO, I already knew what the two anarchists were going to do. They were loud and obnoxious and had already been throwing out ways for the company to make a U-Turn.

But it was the sixth engineer, the quiet, reliable one, who was actually sitting on a good idea. He’d been thinking for years about the idea of status messages over text messaging.

He told us that idea because we asked him to. And we loved that idea. And we asked him to build it. And he turned that idea into Twitter. And he was the first CEO of Twitter.


Do you know what I think is beautiful about this story? It’s a complete reversal of what people think about leadership and potential.

The CEO in this story is Evan Williams, now CEO of Medium.

The engineer with the idea is Jack Dorsey, now CEO of both Square and Twitter.

How great of a leader is Evan Williams? He was able to have the humility to look outside himself, the emotional intelligence to look beyond the loudest voices, and then the resolve to change bets.

And what does Jack Dorsey’s double-CEO, Jobs-ian leadership say about a person’s capacity for self-improvement? Does every one of us who are quietly excelling at our work have the potential to someday run two public companies?

These are the contrarian observations that got me into coaching. What’s the real story behind excellence? The mainstream thinking on leadership wouldn’t have backed Ev and the mainstream thinking on talent would never have identified Jack.

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

Coach Tony

Written by

Evangelist for great coaches and excellent personal development advice. CEO/Founder of Coach.me. Publisher of Better Humans & Better Programming.

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.