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Stewart Butterfield: Embarrassment Can Drive Improvement — Employees Papered the Office

Stewart Butterfield says a little embarrassment can be a productive spur for teams, recounting a 2014 interview in which he called early Slack "terrible." Employees famously printed the quote on 40 sheets of paper and pasted it around the office the next day. Butterfield defends the remark as a way to instill a continuous drive for improvement, citing kaizen and an anecdote about Ray Dalio. He cautions that blunt criticism doesn't work for everyone but can be effective for many.

11:10 PM, 11/23/2025Technology

Stewart Butterfield, cofounder and long-time CEO of Slack, says a healthy dose of embarrassment can motivate teams to get better — sometimes in dramatic ways. In a 2014 interview he described an early version of the product as "just terrible," and the remark had an immediate reaction from staff.

Butterfield recalled on Lenny's Podcast that he arrived at the office the next day to find the quote printed across 40 sheets of 8.5-by-11 paper and pasted all over the walls. While blunt, he defends the comment as a deliberate tool to create what he calls a "perpetual desire to improve."

"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... Like, it's just terrible, and we should be humiliated that we offer this to the public." — Stewart Butterfield

Butterfield clarified that leaders can celebrate individual successes, but should also maintain a mindset that the whole product or organization has "almost limitless opportunities to improve." He pointed to two influences that shape this approach.

Models of continuous improvement

First, he referenced the Japanese principle of kaizen — the practice of continuous, incremental improvement that focuses on maximizing quality, reducing waste, and improving efficiency. Second, he described an anecdote about investor Ray Dalio and a ski instructor who taught the value of learning from mistakes, treating them as "little puzzles" that reveal valuable lessons when solved.

Butterfield acknowledged this style of direct criticism doesn't work for everyone. "Not always, not with every person," he said on the podcast, "but most of the time, with most people, you can get them to the point where that really direct criticism is actually motivational."

Other leaders take similar but distinct approaches to feedback: for example, Netflix's leadership emphasizes "continuous, timely, candid feedback," while Meta's finance chief has noted that Mark Zuckerberg's ability to give constructive feedback has evolved and become stronger over time.

Butterfield went on to lead Slack to become one of the most widely used workplace messaging platforms, culminating in its sale to Salesforce for $27.7 billion.

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