Brian Bailey

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 start and had a hand in everything we built. As the products and teams grew, the knowledge I accumulated felt like a superpower. Not only could I answer most questions, but I could quickly evaluate options and surface trade-offs, edge cases, and unknowns. Decisions weren’t always easy, but with the the full history and context at the ready, they were faster.

Then I started a new job and everything was new again. 37signals has been a successful business for over 20 years. Basecamp debuted in 2004 and HEY recently turned two. The products are both deep and wide, built on principles that guided the thousands of decisions along the way.

It will be a long time before I know Basecamp and HEY inside and out, and that's with a head start. I used Basecamp for the first time in 2004 and frequently in the years since. I signed up for HEY on day one. I've read the books, listened to the podcast, and practiced Shape Up for four years. Even with that context, none of which you normally have when starting a job, I still discover something new most days.

Work at 37signals is remote and asynchronous, with employees in multiple countries and timezones. Outside of the product team, it's unlikely I'll have in-depth conversations with a lot of my coworkers without being intentional about it. So, when I started, I set out to meet as many as possible. 

My motivation was twofold. First, relationships across a company are essential to working in product. Every team has a unique view of the customers and products. There's much to be gained on both sides by an ongoing back-and-forth of insights and ideas, questions and pain points. The best conversations are free-flowing, honest, and fun, which is only possible when you regularly invest in the relationship.

Second, a large portion of the team has been at 37signals for 5, 10, even 15 years. Who better to learn from? These are the people who thoroughly understand the company and the products. They know how things work and why.

The conversations have been a highlight of my first few months. It's a talented and welcoming group of people and everyone has generously shared their knowledge and advice.

One conversation was particularly helpful. At the end, I said I'm eager to learn more from them and others in the weeks ahead. They said that's great, but the organization already has that knowledge. A significant value new people bring is knowledge and perspective the organization doesn't have yet. I should speak up, ask questions, and bring my own knowledge and experience to the table. 

Being an outlier is a feature, not a bug to be fixed as quickly as possible.  

I've been more patient since. Rushing to get up to speed means less time to slow down and look at something with fresh eyes. I don’t always have the context and history, but that’s okay.

Knowing a product completely—it's history, neglected corners, and interconnected pieces—is great, but gaps in knowledge and understanding aren't gaps, they're margin. They make room for new ideas and ways of looking at things.

About Brian Bailey

Head of Product Strategy at 37signals, the friendly people behind Basecamp, HEY, and ONCE. Find me elsewhere at and @bb.