My guest today is Ryan Singer, the head of Project Strategy at Basecamp. Ryan recently published a book called Shape Up where he describes his process for planning, designing, and executing projects at Basecamp. Basecamp works in six-week cycles through the entire company.
In this interview, instead of talking about Shape Up and the principles in the book directly, we danced around those topics and applied them to ideas like consciousness, architecture, and product management. We talked about the interaction between design and consciousness and how Ryan’s love of architecture lead him to Christopher Alexander. We talk about relationships between top-down and bottom-up perspectives on the world and how you can synthesize the two. Our conversation begins by applying Shape Up to the writing process. At times this conversation is practical at times it gets spiritual, and ultimately I hope you enjoy this conversation as much as I did.
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2:02- How Ryan used the core principles of Shape Up to structure, focus, and ultimately write his book, using workshops to refine how you present your ideas and the necessity of using time constraints and process clarification to move through the different processes of writing.
8:29- Ryan’s transition from being a designer to a designing programmer and the successful elements of teamwork that Ryan has identified over his 16 years at Basecamp.
15:13- How impact and team satisfaction drives productivity and focus for Ryan’s team and how the 6-week schedule at Basecamp facilitates this satisfaction. The balance you can find by asking, “How far can you push in one push?”
19:57- How enthusiasm paired with timeboxing helps a team feel energetic but still healthy, the nuance of using a firm 6-week time boundary for a project, and how hard walls with a soft middle are key to the Shape Up method.
26:44- How a team can be committed to the end goal without being attached to how to get there, why Ryan uses the deeply matured truth of architecture to inform his work in the newer field of interaction design and his appreciation of Christopher Alexander’s design principles.
35:18- How only a deep understanding of a problem can inform the comparison methods for the potential solutions, the multiscale principle as relates to Modernist buildings and design, and the playout of human scale and architecture in Minecraft and tourist destinations. Ryan asks the question, “how do we specify the large scale and allow the people living there to design the small scale?”
49:44- Why Ryan chose “Felt Presence” as the name of his website, how consciousness and the mind inform Ryan’s design work, how Bob Moesta’s work to understand why people reach for a Snickers bar informed a redesign of the candy.
55:52- How understanding the underlying causes of a situation can help you design a useful solution.