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

Key takeaways

Embrace a culture of continuous improvement to drive product excellence.
Use Utility Curves to assess the relationship between effort invested and customer value gained.
Focus on comprehension over just friction removal to enhance user experience.
Be aware of the Owner's Delusion: prioritize actual user needs over personal biases in product design.
Generosity in leadership builds trust and fosters a positive organizational culture.
Be rational in determining when to pivot; there's no shame in changing course when data suggests it's needed.

Summary

The Importance of Continuous Improvement

Stuart Butterfield emphasizes the necessity of continual improvement in product development. He shares a candid moment from 2014 when he criticized Slack's launch as a 'giant piece of shit' and explains how this sentiment fuels a culture of constant enhancement within his teams. This mindset reflects a core philosophy: that success is fundamentally tied to the value delivered to customers.

Utility Curves and Product Decisions

Butterfield discusses the concept of 'Utility Curves,' which illustrate a relationship between resources invested in a product feature and the resulting customer value. He explains how initially, small efforts may not yield significant results, but beyond a certain threshold, enhancements can create substantial value. This framework aids product teams in prioritizing resource allocation towards features that effectively meet users' needs.

Friction vs. Comprehension in Product Design

A recurring theme in the conversation is the balance between removing friction and ensuring user comprehension. Butterfield argues that while it is vital to reduce unnecessary friction, product designers must prioritize making things simple to understand. He cites examples of broken interfaces that confuse users and notes that a lack of clarity can lead to frustration, which deters engagement.

The Owner's Delusion and User-Centric Design

Butterfield introduces the concept of 'The Owner's Delusion,' highlighting how product creators often lose sight of user needs in favor of their own preferences. He provides anecdotes about restaurant websites and app features that frustrate users instead of facilitating a positive experience. The key takeaway is that understanding and addressing actual user needs is crucial for product success.

Generosity in Leadership and Culture

The importance of generosity in leadership is underscored, with Butterfield sharing personal anecdotes of his commitment to his team and customers. His actions have included supporting employees in need, adjusting policies in favor of users, and focusing on long-term value creation rather than short-term gains. This generous mindset fosters a thriving workplace culture and cements trust between a leader and their team.

Pivoting: When to Change Course

Butterfield shares insights on pivoting in business, reflecting on his experiences with Flickr and Slack. He offers guidance on when to make the tough decision to pivot, emphasizing the need for rational analysis over emotional attachment to an idea. The ability to evaluate the potential of different paths is essential for growth and adaptation.

Show notes

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

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

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Where to find Stewart Butterfield:

• X: https://x.com/stewart

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

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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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 improvement

(50:03) The complexity of making things work

(54:27) Parkinson’s law and organizational growth

(01:03:17) Hyper-realistic work-like activities

(01:13:23) Advice on when to pivot

(01:18:36) The importance of generosity in leadership

(01:26:34) The owner’s delusion

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Referenced:

• Slack: https://slack.com

• Flickr: https://www.flickr.com

• Cal Henderson on LinkedIn: https://www.linkedin.com/in/iamcal

• Blok: https://blok.so

• Brandon Velestuk on LinkedIn: https://www.linkedin.com/in/brandon-velestuk-6018721b

• Magic Link: https://en.wikipedia.org/wiki/Magic_Link

• Ticketmaster: https://www.ticketmaster.com

• John Collison on X: https://x.com/collision

• Patrick Collison on X: https://x.com/patrickc

• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai

• Three Questions with Slack’s CEO: https://www.technologyreview.com/2014/11/21/170330/three-questions-with-slacks-ceo

• Six Sigma: https://www.6sigma.us

• What is kaizen and how does Toyota use it?: https://mag.toyota.co.uk/kaizen-toyota-production-system

• John Collison’s post on X about passion projects: https://x.com/collision/status/1529452415346302976

• Parkinson’s law: https://www.economist.com/news/1955/11/19/parkinsons-law

• We Don’t Sell Saddles Here: https://medium.com/@stewart/we-dont-sell-saddles-here-4c59524d650d

• Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)

• IRC: https://en.wikipedia.org/wiki/IRC

• This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke

• The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins: https://www.lennysnewsletter.com/p/the-making-of-canva

• Prisoner’s dilemma: https://en.wikipedia.org/wiki/Prisoner%27s_dilemma

• Stewart Little: https://en.wikipedia.org/wiki/Stuart_Little

• Dharma and Greg: https://en.wikipedia.org/wiki/Dharma_%26_Greg

• Stewart’s post on X referencing “the owner’s delusion”: https://x.com/stewart/status/1223286626991796224

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Recommended books:

• Principles: Life and Work: https://www.amazon.com/Principles-Life-Work-Ray-Dalio/dp/1501124021

• Why Nothing Works: Who Killed Progress―and How to Bring It Back: https://www.amazon.com/Why-Nothing-Works-Killed-Progress_and/dp/154170021X

• Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586

• Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996

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Lenny may be an investor in the companies discussed.

To hear more, visit www.lennysnewsletter.com