Brian Bailey

Head of Product Strategy at 37signals. Now writing at world.hey.com/bb
August 4, 2024

5 Years of Shape Up

Shape Up debuted 5 years ago on July 10, 2019. I remember it because I read the book from cover to virtual cover the day it came out. I was leading product at a small startup. We were using a version of Shape Up that I'd stitched together from blog posts and podcasts. We had left 2-week sprints and backlog grooming behind and product d...
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April 11, 2024

Leave room

HEY Calendar has a feature called Time Tracking. It's one of those things that once you have it, you wonder why every calendar app doesn't. What better place to track time? Today we shipped a handful of improvements that make it that much nicer. One change is when you look at a category, we total up the number of hours for you. That re...
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April 6, 2024

Too quiet

When you walk to your favorite coffee shop, you pass a woodworking shop that makes custom furniture. You can watch them work through the large, glass doors. When the weather is just right, they even prop them open. After admiring the creations for months, you place an order for the bookcase you've always wanted. They star Monday and it...
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March 28, 2024

Anatomy of an Announcement

Announcements tell the ongoing story of a product. They frame new features, suggest different ways of using the product, and pull in curious people who haven't signed up yet. They're also easy to tune out. Here are a few ways to make them worth reading. 1. Tell a friend Starting here makes everything easier. Imagine you're at a coffee ...
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March 11, 2024

Consider it done

If you're an author, the moment comes when you hand off the final draft and the book is published. If you make music, you eventually stop altering the mix and cycling through cover photos. You finish the album and release it. The book might have a convoluted plot. Maybe the album could use more insightful lyrics. But they're done. Most...
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December 20, 2023

Two heads

Product roles are frequently solo roles. There's a lot of collaboration with designers and engineers, but it's uncommon that two product people work alongside one another. That's why you hear a lot about being the "CEO of the product" or owning things, whether a product, feature, flow, or metric. The list of reasons I wanted to join 37...
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November 20, 2023

Make room for ambition

You start a new project. The pitch outlines the problem and boundaries of the solution. There's an appetite, like three weeks, that captures how much time it's worth investing. It's time to jump in. You add some to-dos. Have a kickoff call. Mock up a few approaches, throw together a dead simple UI, or spike a potential data model. All ...
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September 12, 2023

Strict scrutiny

The Betting Table is how product priorities are chosen in Shape Up. It’s essentially a planning meeting—priorities are debated, projects picked, and teams finalized—but, it still prompts a lot of questions. What’s so different? Let’s start with the basics. The meeting is three people: Jason (CEO), David (CTO), and myself (Head of Produ...
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September 4, 2023

Margin

You can’t have margin without constraints. At 37signals, we work in 6-week cycles. At the end of the 6 weeks, whatever we’re building has to ship. After the cycle, we have a 2-week cool-down where people can roam, experiment, and fix a nagging frustration or two. It's also a chance to slow down, reflect, and recalibrate. The cool-down ...
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July 1, 2023

Often, not always

Do you optimize for consistency or flexibility? Many of us are drawn to patterns and processes. When something goes well, we try to figure out how to repeat the success. “That project went great. Let's do the same thing next time.” When things go poorly, we look for which inputs led to the wrong output. Then, we introduce checkpoints t...
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March 22, 2023

Lessons in shaping

When I joined 37signals last year, I had been using Shape Up for four years, but I was eager to learn how shaping here differed from my own experience. I wasn't disappointed! Jason and David share invaluable feedback during shaping and at the betting table, as do the programmers and designers who take a pitch and turn it into something...
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July 29, 2022

The pizza or the toppings

Product strategy is continually asking, What is the pizza, and what are the toppings? What defines a pizza? At it's core, it's a round base of dough baked with a topping of tomato sauce and cheese. If you're opening a restaurant and want to be known for great pizza, that's where to start. Experiment over and over again until you perfec...
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July 17, 2022

It's okay not to know

From the start of my career, I've known the products I've worked on inside and out. Not only how they work, but why they work that way—from how one feature intertwines with another to the reasons others were never built. Joining two startups while the employee count was still in the single digits made it easy. I was there from the star...
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June 2, 2022

New job, same desk

One twist of remote work is that when you get a new job, you don't get a new office. I started at 37signals last month. We make Basecamp and HEY (and HEY World!) The company is fully distributed, with employees around the world. I’m working on product strategy from my home office in Austin. Which happens to be the same home office I wo...
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