Shape Up with Ryan Singer

  • What is Shape Up? Shape Up is a detailed guide to how product development is done at Basecamp. [0:27] 

  • What is the book about? The book is about structuring work in such a way that teams don’t have a huge backlog. Teams don’t have any hazily defined, morale draining projects. No projects that stretch on-and-on. [0:38]

  • How do we know if the thing we are making is the right thing? This was the conversations we were having in the company. They felt like they were the most important conversations. It was natural for me to put more of my time into that side of things [product strategy]. [4:19]

  • Where the idea for Shape Up came from: Jason Fried suggested to me that he thought it was time to write a book and share what we figured out about how to work. He said I should write a book about that. [4:43] 

  • Before writing the book: I decided to hold a workshop as a prototyping device. I made it expensive enough that everyone who came would be really motivated. It was $1,000 a seat for one day. This gave me the opportunity to explain [and get feedback on] what I thought was meaningful: How we shape work, why we work in 6 weeks cycles, how teams work together, how we assemble projects etc. [5:37]

  • Inspiration for the rough, authentic look of Shape Up: When I was younger there were these little books sold at Radio Shack. Every book was hand drawn on graph paper. The author hand wrote it and interspersed the book with his little sketches. Millions of these things have sold. Those books gave me the confidence that things don’t have to be polished or professional looking. [7:02] 

  • Something I didn’t know was a problem before the workshop: When designing a product people feel like they get pushed into too much detail too early. [8:53]

  • A major theme of the book: Working with boundaries and constraints. Embracing them. Seeing boundaries and constraints as a helpful tool, rather than a road block. [13:35]

  • We don’t have this giant list of things we have to do one day: Other companies create this big backlog of stuff. There is more on that list than you could ever do. It creates a bad feeling. That sucks. [Another reason to always work on your top priority] [13:59]

  • The word bet is better than the word plan: Plan has a feeling of certainty. But the reality is you don’t know what is going to happen. [16:19]

  • We have this thing called a circuit breaker: It is a very effective and severe policy. If the thing doesn’t get done in the time we give it is automatically cancelled. [19:14]

  • Work on what is most important now: Just because a task was important in the past doesn’t mean it is relevant now. [20:50]

  • What do you want to do? If you don’t know what you want, no method can help you. [25:29]

  • Full podcast here.