Design for Understanding, Not Just Frictionless Use

Resources

Resources & Recommendations

Books

• "Why Nothing Works" by Unknown Author - This book explains the progressive increase in vetoes available for any course of action and how difficult it is to get things done in complex systems.
• Annie Duke's Second Book (Title not recalled by speaker) - This book uses Glitch and Slack as examples of making smart "folds" or pivots when the expected value of one path diminishes.
• "Don't Make Me Think" by Steve Krug - This book's mantra is about making software intuitive and easy to use, minimizing cognitive load for users.
• "Positioning: The Battle for Your Mind" by Al Ries and Jack Trout - This classic marketing book emphasizes that it's easier to position a product by connecting it to existing ideas in a user's mind rather than introducing entirely new concepts.

People Mentioned

• Noah Weiss - Suggested topics and questions for the conversation.
• Chris Cortel - Suggested topics and questions for the conversation.
• Ali Rail - Suggested topics and questions for the conversation.
• Johnny Rogers - Suggested topics and questions for the conversation.
• Cal Henderson (CTO of Slack) - Mentioned as Stewart Butterfield's long-time collaborator, having worked together for 23 years on Flickr and Slack.
• Jeff Bezos (Founder of Amazon) - Referenced for his quote "your margin is my opportunity" and the concept of "divine discontent."
• Brendan Velasco (Former Creative Director for Product Development at Slack) - Mentioned in the "tilting your umbrella" anecdote, which became a core value at Slack.
• Andrew Torres - Possibly one of the individuals who came up with the "magic link" idea for Slack's mobile app.
• Ben Brown - Possibly one of the individuals who came up with the "magic link" idea for Slack's mobile app.
• John Collison (Co-founder of Stripe) - Mentioned in an anecdote about his frustration with the Gmail app's contact dragging feature.
• Sundar Pichai (CEO of Google) - Mentioned in an anecdote about his conversation with John Collison regarding the Gmail app.
• Michael Jordan - Referenced for his approach to learning to ski, viewing every mistake as an opportunity for improvement.
• Farid (last name not mentioned) - Suggested asking about "hyper realistic work-like activities."
• Melanie Perkins (CEO of Canva) - Mentioned as an example of perseverance, having been rejected by 100 investors before finding funding.
• Stewart Little - The mouse character, mentioned in the context of Stewart Butterfield's name choice.
• Dharma (from Dharma & Greg) - The character, mentioned in the context of Stewart Butterfield's original name.

Organizations & Institutions

• MIT Technology Review - Interviewed Stewart Butterfield in 2014 about Slack's progress.
• The Economist - Published Parkinson's original article on Parkinson's Law in 1956.
• Bridgewater - Mentioned in the context of a story about Michael Jordan learning to ski.

Websites & Online Resources

• lenny'snewsletter.com - Mentioned as a place to become an annual subscriber and receive free products.

Other Resources

• Utility Curves - A concept describing an S-curve where initial effort yields little value, followed by a steep increase in value, and then diminishing returns. It helps determine where to invest product resources.
• Owner's Delusion - A concept describing how product creators often design for their own understanding and intent rather than the user's, leading to confusing or unhelpful experiences.
• Hyper Realistic Work-Like Activities (HRWLA) - A term coined by Stewart Butterfield to describe activities that superficially resemble productive work but do not contribute to known valuable outcomes, often stemming from an oversupply of people and a lack of clear, valuable tasks.
• Parkinson's Law - The maxim that "work expands to fill the time available for its completion," often leading to organizational bloat and inefficiency.
• We Don't Sell Saddles Here Memo - A legendary internal memo from Stewart Butterfield at Slack emphasizing the importance of communicating the value and outcomes of a product to users, not just its features.
• Shouty Rooster - An internal name for a feature in Slack that warns users when they use the "@everyone" tag, preventing overuse and annoyance.
• Magic Link - A login method where a link is sent to a user's email for authentication, eliminating the need to type a password.
• Divine Discontent - A term used by Jeff Bezos to describe a perpetual desire for improvement and dissatisfaction with the current state of things.
• Tilting Your Umbrella - An anecdote that became a core value at Slack, representing empathy, consideration, and attention to detail in product design.
• Prisoner's Dilemma - A concept from game theory mentioned in the context of demonstrating cooperation through acts of generosity.
• Fair Billing - A Slack policy that stopped charging customers for unused seats, seen as a generous and innovative approach to customer relations.