Stewart Butterfield, Cofounder and CEO of Slack

Key ideas

Butterfield recounts two failed games that became Flickr and Slack, what shutting one down cost people, and how leading at scale changed the weight of his words.

From a machine transcript of the audio. Quotes link to the moment they are said.

1. 1

   A failed project can hold the next

   Butterfield says his first game could not raise money after the dot-com crash, so the team looked for a viable use of its technology, and that became Flickr after a tied team vote and some lobbying by him. His second game fell short too, and the internal system built on IRC to log and search messages became Slack, once the team realized they would not want to work without it. He says he only recognized much later how similar these products were.

2. 2

   Shut down with the people in mind

   Butterfield says stopping the game Glitch meant laying off people whose skills did not transfer, ending a community and facing what he had promised press, investors and staff. The hardest moment he describes is meeting the eyes of someone he had recently persuaded to move his family for the job. He says the $5.5 million left paid for a portfolio site, reference letters and career coaching, and customers were offered refunds, though he says none of that changed how the moment felt.

3. 3

   Make it explainable by the listener

   Butterfield says Slack was slow to spread at first because it replaced nothing, and that a new concept struggles to find a place in someone's mind. He treats it as a problem if the person you explain a product to cannot explain it to the next person, because then you must do all the explaining. He says the encouraging sign was that teams who tried it almost always stayed.

4. 4

   At scale, your words weigh more

   Butterfield says that at thousands of people, a routine 30-minute review for him can be something a new employee has prepared for over weeks, and it may be their only contact with him for years. He says any criticism therefore carries far more weight, and that he has been learning to lead without crushing people or ruling from the top. He describes the deeper challenge as not seeing others as either instruments or obstacles.

5. 5

   Start on diversity early

   Butterfield says Slack noticed its makeup at around 20 to 30 employees, which was close to too late, because each hire changes how the next candidate sees the company. He thinks the belief that hiring outside the usual profile lowers the bar is usually untrue, arguing that looking harder shows you more people. He also argues that, on the whole, candidates without the usual networks have overcome more to reach the same point.

In Stewart’s words

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