For Slack cofounder Stewart Butterfield, embarrassment can be a useful and motivating tool.
Butterfield led Slack, which is now owned by Salesforce, from 2009 to 2023 as CEO. In 2014, he gave an interview where he called the early product “terrible.” Employees responded by putting posters up around the office, he said on “Lenny’s Podcast” — but he stands by it.
“I try to instill this into the rest of the team, but certainly I feel that what we have right now is just a giant piece of shit,” he told the MIT Technology Review in 2014. “Like, it’s just terrible, and we should be humiliated that we offer this to the public. Not everyone finds that motivational, though.”
On the podcast, Butterfield described the aftermath.
“I came into the office the next day and people had printed out on 40 pieces of 8.5-by-11 paper that quote and pasted it up on the wall,” he said.
Butterfield defended what he had said in the 2014 interview: “To me, that was like: you should be embarrassed by it. It should be a perpetual desire to improve. You should never be like, ‘Oh, this is great.'”
He could be proud of “individual pieces,” Butterfield said, but in the aggregate, leaders should only see the “almost limitless opportunities to improve.”
Butterfield gave two examples of the endless search for improvements.
First, he pointed to Toyota’s principle of “kaizen,” or continuous improvement. The philosophy ensures “maximum quality, the elimination of waste, and improvements in efficiency,” per Toyota’s UK magazine.
Second, he pointed to Bridgewater founder and billionaire investor Ray Dalio. Michael Jordan’s ski instructor once told Dalio that he “reveled in his mistakes” and saw them as “little puzzles that, when you solve them, give you a gem.”
How to be critical — and when — is an art that all leaders approach differently. Netflix’s CTO said that the company uses “continuous, timely, candid feedback.”
Meta CFO Susan Li said that Mark Zuckerberg has refined his ability to give feedback over the years. Now, he’s “world-class,” Li said.
On the podcast, Butterfield said that “trying to be critical” and “trying to find improvements” can be helpful tools.
“Not always, not with every person,” he said. “But most of the time, with most people, you can get them to the point where that really direct criticism is actually motivational.”
Butterfield would go on to lead Slack to become one of the most popular workplace messaging platforms in the world, eventually selling it to Salesforce for $27.7 billion.
