How To Ship Work That Matters with Basecamp’s Ryan Singer

On this episode Abadesi talks to Ryan Singer, head of Product Strategy at Basecamp, where he’s worked for 16 years, ever since 2003. He is the author of Shape Up: Stop Running in Circles and Ship Work That Matters. You can read the book for free online.

In this episode they talk about...

How Basecamp cultivates their unique company culture

“If you think something is going to work, then go make it and let’s look at what you made in two or three days or a week. If you can’t make anything yet that works, maybe it’s not real and not ready yet. Don’t make me a big document about how it’s going to work — let’s make a prototype and click on it and see if it’s going to work.”

Ryan says that he was initially a UI designer and got into programming after joining Basecamp. He was at what was then called 37signals when Ruby on Rails was being created. He talks about the culture of shipping at Basecamp and how the learnings from his sixteen years at the company have made it into the book.

Why wireframes and documents are overrated

“If we over-specify the design up front with a lot of wireframes, we make the most decisions when we have the least information.”

Ryan says that at Basecamp, they use breadboards and fat marker sketches to mock up potential products, rather than detailed documents or pixel-perfect wireframes. He explains why it’s important to allow for improvisation by the designers and developers of products, and why you shouldn’t make the key trade-offs in the design phase, but instead after you’ve seen and used a prototype. He says that you “need to find the right level of abstraction” in your designs.

Why betting is better than planning

“We acknowledge the reality, which is that we don’t know what’s going to happen, we don’t know how this is going to work out, we’re probably going to be wrong about some things, so we want to use the language of risk instead of the language of certainty.”

At Basecamp, instead of making plans, they make bets. Ryan explains why this provides a better framework for the work that they do. He points out that when you make bets, you bet a fixed amount. They do the same at Basecamp, “betting” a certain amount of time on a project to see if it will work. If at the end of that time, it didn’t work out, they don’t spend more time than they originally “bet” on it chasing sunk costs.

How to find balance at work, and why Basecamp doesn’t think about “maximizing capacity”

Ryan says that they don’t think about “maximizing capacity” from their employees. Instead, they want to make sure that their workers have a meaningful goal with good odds for success. He says that managing how many hours someone worked the day before or today means very little. His advice is to stop micromanaging employee time and to experiment with a more flexible approach at your company. He also points out that they try to think about strategy at a more macro level than in terms of days or hours.

How to separate strategic failure from execution failure

“I would much rather have a healthy team that’s good at shipping stuff and occasionally make a strategic mistake. Because our bets have a limited downside, we’re setting out how much it is worth at the beginning. We only lose however much time we set out initially.”

As part of their unique approach to strategy, they are able to manage their downside by setting out the amount of time they’re willing to spend on something in the beginning. They trust their teams to figure out the details of the work on their own, without prescribing every detail of the product in the beginning. He explains how this is important to morale and what the difference between “imagined work” and “discovered work” is.

Ryan also talks about his love for the Apple Pencil and the iPad, and how he uses them to get his work done.

Bonus Content: Aba and the community on personal branding

We have more bonus content for you this week! Aba recently hosted a Periscope session where she invited all of you in the community to call in and explain what sites you use for personal branding and why. They covered LinkedIn, Medium, Twitter, personal sites, mailing lists, and more. If you want to be part of the next session (and maybe even be part of the podcast!) be sure to follow us on social media.

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Companies and Products Mentioned In This Episode

iPad + Apple Pencil

The Economist’s Mobile App