“What we have right now is a giant piece of …,” says Slack cofounder Stewart Butterfield on building a culture of improvement

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Slack cofounder Stewart Butterfield has never shied away from blunt assessments — especially of his own product. Reflecting on Slack’s early days, Butterfield revisited a moment from 2014 when he described the then-nascent messaging tool in language few CEOs would dare to use publicly. Speaking to MIT Technology Review at the time, he said: “What we have right now is just a giant piece of shit.” The remark would become one of the most memorable in the company’s history, not just because of how sharp it sounded, but because of how employees reacted.

The next morning, Butterfield walked into Slack’s office to find his words printed out across 40 sheets of paper and taped to the walls. It was part protest, part inside joke, and part reflection of how the team internalised his call for constant improvement. Rather than back away from the critique, Butterfield still stands by the sentiment today. As he explained on Lenny’s Podcast, embarrassment — when channeled correctly — can be a powerful motivator. His view: teams should never settle, never assume the product is “great,” and always maintain what he calls a “perpetual desire to improve.”

According to Butterfield, leaders should embrace a mindset that sees flaws as opportunities. He pointed to Toyota’s kaizen philosophy — the belief that organisations should continuously eliminate waste and increase efficiency — and to Ray Dalio’s habit of treating mistakes as valuable “little puzzles.” In Butterfield’s interpretation, the job of a founder is not only to build a product but to keep finding places where it falls short. Even when Slack began gaining traction and winning praise, he maintained a sceptical posture, saying leaders should focus less on individual wins and more on the “almost limitless opportunities to improve.”

Still, he acknowledged that this form of direct criticism isn’t for everyone. “Not always, not with every person,” he said on the podcast. But in most cases, he believes people can learn to treat tough feedback as motivation rather than discouragement. It is, in his view, part of building a culture where honesty is normal and complacency is rare.
Slack would eventually evolve from that “terrible” early version into one of the most widely used workplace messaging platforms, culminating in its $27.7 billion acquisition by Salesforce. But for Butterfield, the lesson of those early days remains unchanged: if you’re building something important, you can’t be afraid to call out its flaws — even if your team turns your words into wallpaper.