Slack founder: Mental models for building products people love ft. Stewart Butterfield

Slack founder: Mental models for building products people love ft. Stewart Butterfield

November 20, 2025 1 hr 30 min
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🤖 AI Summary

Overview

This episode features Stewart Butterfield, co-founder of Slack and Flickr, as he shares his insights on product design, leadership, and the principles that have guided his success. From the importance of utility curves to the concept of hyper-realistic work-like activities, Stewart offers practical frameworks for building products that resonate deeply with users and creating organizations that thrive.

Notable Quotes

- If you can't see almost limitless opportunities to improve, then you shouldn't be designing.Stewart Butterfield, on the importance of continuous improvement.

- In the long run, the measure of our success will be the amount of value we create for customers.Stewart Butterfield, emphasizing the core metric of business success.

- Don't make me think.Stewart Butterfield, on reducing cognitive load for users in product design.

🛠️ Utility Curves and Product Design

- Stewart explains the utility curve, a concept that helps teams determine whether a feature is worth further investment.

- The curve illustrates how initial effort yields minimal value, followed by a steep increase in value, and eventually plateaus.

- He emphasizes the importance of reaching the aha moment where users can't live without the product.

- Stewart highlights the need for continuous improvement, citing examples like Slack's notification settings and the magic link login feature.

🌂 Tilting Your Umbrella and Product Craftsmanship

- Stewart shares the metaphor of tilting your umbrella, which became a cultural value at Slack. It represents the importance of empathy and consideration in product design.

- Slack's success was partly driven by small, thoughtful touches that created emotional connections with users, such as the shouty rooster feature to prevent overuse of @everyone notifications.

- He argues that good taste in product design can be cultivated and is a competitive advantage, as most companies fail to invest in it.

🧠 Friction vs. Comprehension in User Experience

- Stewart challenges the common mantra of reducing friction in product design, arguing that the real challenge is often user comprehension.

- He explains that reducing friction is only valuable when users have clear intent and understanding of the product.

- Instead, designers should focus on making products intuitive and reducing the cognitive load on users.

- He cites examples like Slack's onboarding process and the importance of clear visual hierarchies and affordances in UI design.

🔄 The Art of Pivoting

- Stewart reflects on his experience pivoting both Flickr and Slack from their original concepts as video games.

- He advises founders to pivot only after exhausting all realistic ideas to make the current concept work.

- He emphasizes the importance of making rational, not emotional, decisions when considering a pivot, despite the humiliation and difficulty it may involve.

🎭 Hyper-Realistic Work-Like Activities and Leadership

- Stewart introduces the concept of hyper-realistic work-like activities, where employees engage in tasks that mimic real work but lack meaningful impact.

- He attributes this phenomenon to the natural tendency of organizations to grow and create unnecessary work.

- Leaders must take responsibility for providing clarity and ensuring a steady supply of known valuable work to prevent teams from falling into this trap.

- He highlights the importance of saying no to low-impact initiatives and fostering alignment around priorities.

AI-generated content may not be accurate or complete and should not be relied upon as a sole source of truth.

📋 Episode Description

Stewart Butterfield is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions, he’s been focused on family, philanthropy, and creative projects. In this rare podcast appearance, Stewart shares the product frameworks and leadership principles that most contributed to his success. From “utility curves” to “the owner’s delusion” to “hyper-realistic work-like activities,” his thoughts on craft, strategy, and leadership apply to anyone building products or leading teams.

We discuss:

1. Hyper-realistic work-like activities

2. The owner’s delusion

3. Utility curves

4. “Don’t make me think”

5. “We don’t sell saddles here”

6. Tilting your umbrella

7. When to pivot

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Transcript: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/178320649/my-biggest-takeaways-from-this-conversation

Where to find Stewart Butterfield:

• X: https://x.com/stewart

• LinkedIn: https://www.linkedin.com/in/butterfield

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Introduction to Stewart Butterfield

(04:58) Stewart’s current life and reflections

(06:44) Understanding utility curves

(10:13) The concept of divine discontent

(15:11) The importance of taste in product design

(19:03) Tilting your umbrella

(28:32) Balancing friction and comprehension

(45:07) The value of constant dissatisfaction

(47:06) Embracing continuous