Mental models for building products people love ft. Stewart Butterfield

Episode Overview

• Stewart Butterfield shares his core product-building philosophy, which is rooted in a deep, self-critical dissatisfaction with the current product and an unwavering focus on creating customer value.
• He challenges the conventional wisdom of simply "reducing friction," arguing that the true goal is to increase user comprehension and reduce cognitive load, encapsulated by the mantra "Don't make me think."
• Butterfield applies Parkinson's Law to modern organizations, explaining how "hyper-realistic work-like activities" emerge when teams lack a clear supply of valuable work, leading to bloat and wasted effort.
• The discussion covers his approach to leadership, from making cold, rational decisions during difficult pivots to using strategic generosity to foster a cooperative and successful company culture.

Key Concepts

• Divine Discontent: The belief that a product leader should always be embarrassed by their product's current state and see "limitless opportunities to improve," driving relentless innovation.
• Customer Value as the North Star: The ultimate measure of a company's success is the amount of value it creates for its customers, a principle so central at Slack it was turned into a company-wide chant.
• Comprehension Over Frictionlessness: The goal of product design isn't just to remove clicks but to reduce cognitive load. Thoughtful friction can be beneficial if it helps a user understand the consequences of their actions.
• Shaping User Behavior: Using gentle nudges and educational friction, like Slack's "Shouty Rooster" warning for @everyone notifications, to guide users toward more considerate and effective use of a product.
• The Power of Defaults: Smart defaults are a critical tool for driving the adoption of beneficial features, as most users will not opt-in on their own.
• Rational Pivoting: The process of changing a company's direction must be a logical, intellectual decision, made with emotional distance to overcome the "humiliating" feeling of admitting the original plan failed.
• Parkinson's Law in Organizations: The principle that administrative work and staff tend to expand to fill available time, not because of malice, but due to the rational, self-interested behavior of individuals seeking to grow their influence by hiring subordinates.
• Hyper-Realistic Work-Like Activities: Tasks that look and feel like productive work (e.g., meetings, presentations, analysis) but ultimately create little to no value for the customer. These often arise when there isn't enough genuinely valuable work to do.
• Strategic Generosity: A leadership style based on game theory, where acts of generosity and goodwill are used to demonstrate a cooperative stance, fostering a more trusting and successful long-term organizational environment.

Quotes

• At 0:08 - "I feel like what we have right now is just a giant piece of shit." - Stewart Butterfield, recalling a quote from a 2014 MIT Technology Review interview about the state of Slack shortly after its launch.
• At 0:18 - "If you can't see almost limitless opportunities to improve, then you shouldn't be designing the product." - Butterfield explaining the mindset he believes is necessary for anyone in a product leadership role.
• At 1:09 - "How can I make this simple? How do I prevent people from having to think in order to use my software?" - Butterfield on the questions product builders should ask instead of just focusing on reducing clicks or friction.
• At 1:25 - "...make an intellectual, rational decision about it rather than an emotional decision is essential." - Butterfield’s advice on the mindset required to successfully navigate a company pivot.
• At 24:32 - "Hey, this is going to cause a notification for 147 people in eight different time zones. Are you sure you want to send this message with the @everyone?" - Describing the warning message that appeared when a user tried to notify an entire channel, which served to educate them on the consequences of their action.
• At 24:47 - "It was really trying to shape people's behavior so that they use—we wanted Slack to be very flexible, but we knew that there was ways to use it that would be annoying and and difficult for everyone." - Explaining the core philosophy behind designing gentle nudges and "light friction" into the product to guide users toward more considerate communication habits.
• At 27:48 - "Critically, with setting a bunch of defaults, because if we didn't set the default, most people wouldn't turn it on at all." - On the rollout of the Do Not Disturb feature, emphasizing the immense power of defaults in driving the adoption and benefit of a new feature.
• At 36:59 - "If there was one mantra that I would use to replace that, it's 'Don't make me think'." - Offering a better principle than "reduce friction," suggesting the primary goal should be to minimize the cognitive load and uncertainty for the user.
• At 37:44 - "You make me feel stupid... if you're causing people to think, in the best case, it's an unnecessary use of their biological resources, and in the worst case, you've now made them feel bad." - Explaining the negative emotional and cognitive cost of forcing users to decipher a confusing interface or make a decision they don't understand.
• At 54:42 - "Work expands to fill the time available for its completion." - Stewart defines Parkinson's Law, an adage from a 1956 article in The Economist.
• At 57:16 - "It's not because people are evil and it's not because they're stupid... in fact, they're smart." - Stewart clarifies that the tendency for organizations to bloat isn't due to bad intentions but rather rational, self-interested behavior within a corporate structure.
• At 1:01:52 - "[It was] thousands of person-hours, at a minimum, because any feature change at that scale of organization is involving a dozen people... it's a guaranteed loser." - Stewart details the massive, wasted effort on a trivial product change at Slack, highlighting how "hyper-realistic work-like activities" can consume huge resources.
• At 1:03:31 - "Hyper-realistic work-like activity is superficially identical to work... we are sitting in a conference room and... something is being projected... we're all talking about it, and that's exactly what work is." - Stewart defines the term, explaining that these activities mimic real work but lack real value.
• At 1:05:14 - "Acts of generosity to me are a way of demonstrating that I am going to cooperate as we iterate in this game." - Stewart explains that his generous leadership style is partly innate and partly a strategic, game-theory-based approach to foster a cooperative and trusting environment.
• At 1:08:23 - "In the long run, the measure of our success will be the amount of value we create for customers." - Stewart recites the mantra he had the entire company chant at all-hands meetings to instill a deep focus on customer value.

Takeaways

• Cultivate a mindset of "divine discontent" with your own product; always see its flaws and opportunities to fuel relentless improvement.
• Center your entire company's mission on creating customer value and make it a tangible, repeated mantra to align every team's efforts.
• Shift your product design goal from "reducing friction" to "reducing cognitive load." The best experience is one that prevents users from having to think.
• When facing a major pivot, make a cold, rational, and intellectual decision, separating it from the natural feelings of humiliation or failure.
• Use small moments of "good friction" to educate users and gently shape their behavior for a better collective experience.
• Maximize the adoption of beneficial features by enabling them with smart defaults, recognizing that most users will not opt-in themselves.
• Proactively combat organizational bloat by scrutinizing work that doesn't add direct customer value and questioning hiring that creates unnecessary layers of management.
• As a leader, ensure your team has a clear and sufficient supply of "known valuable work" to prevent them from filling their time with low-value, "hyper-realistic" tasks.
• Practice strategic generosity in leadership; small acts of goodwill signal a cooperative stance that fosters trust and a healthier, more effective long-term culture.