(2025-11-24) Rachitsky Biggest Takeaways From Stewart Butterfield

Lenny Rachitsky: My biggest takeaways from Stewart Butterfield.

1. Product design is about creating understanding, not removing friction. Teams obsess over reducing friction and removing steps, but 70% to 80% of product design challenges are actually about helping people understand what your product does and what to do next.

2. You’re not selling features—you’re selling outcomes.

3. Organizations naturally fill with fake work (bullshit work) that looks exactly like real work, what Stewart calls “hyper-realistic work-like activities.” Meetings to preview deck slides, analysis of tiny feature differences, elaborate processes around insignificant decisions. People aren’t lazy; they’re responding to having more time than valuable work to do. Leaders must continuously ensure there’s enough valuable work and explicitly say no to projects that can’t possibly generate meaningful impact.

4. Small conveniences create emotional connections that drive word-of-mouth growth. No one switches products because of a good time-zone picker or smooth password recovery, but these details make users love or hate your product.

5. The “owner’s delusion” explains why bad experiences persist everywhere. Restaurant owners create terrible websites even though they’ve experienced the frustration of visiting other terrible restaurant websites. Business owners assume visitors care deeply about their product, when in reality people arrive distracted, in a hurry, just above the threshold of caring at all. (this drives way too many re-design projects)

6. Only pivot after exhausting all reasonable ideas. The right time to pivot isn’t when things get hard—it’s when you’ve genuinely tried every non-ridiculous approach and can coldly, rationally assess that the expected value has dropped below alternatives.