Ryan Singer of Basecamp about brainstorming and innovating remotely


When you think about remote work, Basecamp is likely one of the first things that come to mind. What used to be a Chicago-based web agency called "37signals" turned into a globally known product for collaboration and async communication. With multiple books published and a culture that lives and breathes remote, they were advocates of distributed working for the better part of the past decade.

Ryan Singer has been part of that journey for 17 years, starting in design, moving over to coding, and now sitting in-between the two as the Head of Product Strategy. In this interview, we are talking to him to find out more about how this all started, and how the transition from a quiet Chicago-based office to a remote life in the mountains went.


"Today, things are more formalized"

Hey Ryan, thanks for meeting with me! You are the Head of Product Strategy at Basecamp. I am sure most of our readers know what Basecamp does, but if anybody doesn't – could you summarize it for us?

Basecamp is an online communication platform for teams working on projects together. In my time here, I've been through a few titles and positions. When I first joined we were still doing web design work for clients as 37signals, so I joined as a web designer. Later, I moved on to become an interface designer on Basecamp, the product.

At some point, I started learning to program and work together with the programmers. Eventually, we went with the title 'Product Manager', even though it wasn't quite clear what that meant at the time. We wanted to indicate that I was working between the spheres of design and programming. Today, it's Product Strategy.

Basecamp has transformed a lot – you went from working in a consulting position to being a company with a single product. How did your job change throughout that?

The biggest thing that changed in my role is that it was extremely hands-on and I was working very directly with Jason and David every day when we were first building Basecamp. Today with 50-something people, there's more processes and more formality with what we do and how we do it.

I think that change is part of what has enabled us to formalize the way that we work into 'Shape Up', the book that I wrote last year. You need to formalize the way that you work as you bring on more people, and become more clear about what the steps are. We're still extraordinarily flat and there's still a lot of autonomy and freedom, but there's some clearer structure overall.

We've gone through different phases, where Basecamp was the only product and then we had a whole suite of products sold together at some point. Then, for a while, we were focused on just Basecamp as the main thing and now, Jason and David are ready to ship their new product called Hey very soon. Now again, we'll have two main products and we'll see what comes next.

You have not only been iterating on existing ideas then but actually built a new thing from scratch while remote. How has that process been like, to brainstorm and work on an entire product without seeing anyone in person?

It's actually not so different from what we've been doing for Basecamp. I'd usually have my head down working on the main changes or a new feature and then I'll have a call with Jason and do a working session with him. It's not like a meeting, it's just a call where we look very closely at the work that I've done and take care of the questions that I'm raising. We'll talk through some of the ideas and we'll have these close one-on-one sessions, a lot of results come out of those.

It's not as good as being in the same room and drawing together on a blackboard on the wall, I think that's the best environment for that type of sketching and brainstorming, but it hasn't been horrible. I don't think we suffered too much from not having that.

Before the outbreak, I would fly to Chicago, maybe once a quarter, and then Jason and I would have a couple of intensive days in a room together. That would be an opportunity to catch up on all of the things that are more creative. Those moments together in a room are a good opportunity to take everything that is unclear and fuzzy and talk it through, draw some sketches on the wall, and then come to some understanding with each other.


"I haven't found an equivalent to sketching and brainstorming in person"

What's keeping you from doing the same thing over a video call?

I haven't found any type of an equivalent to the experience of standing up, grabbing a piece of chalk and drawing on the blackboard. There's a dynamic in those situations where you draw something, and then the person that you're with grabs the chalk and they stand up and draw something next to it. Having this kind of shared surface, there's a certain kind of spontaneity in that process, that I have not been able to replicate online yet. I don't think any of the online tools are a good substitute for that.

Also, there's something about getting in the room together and carving out this time together, where you know that this is what you're going to do for the afternoon. If you have this open time, anything can come up. I feel like when it comes to zoom calls and phone calls, it feels more limited – we have this scheduled hour and not more. If you were to try and sit together on a Zoom call all day, it wouldn't be fun, you would get tired of it pretty fast. It's hard to get that feeling of being in the bubble together for the day, and just sort of carving out that time and space to be creative together.

What I'm finding is that there's always a tradeoff. On the other hand, if Jason and I were to meet in person in Chicago, I would go there and just see what comes out of the conversation. When we meet over zoom remotely, I feel like I need to have a lot more prepared, because I need to use the time better. If I do my homework and go into it prepared, I find that it's actually a very intense and very productive session.

You have that office in Chicago. Do you have people going there every day, exactly because of this trade-off?

It used to be the case that a lot of our core team was in Chicago. It was more regular for Jason and me to get together into a room to brainstorm something. As the company started to grow, we started to meet a little bit more infrequently, but more intensely. It came to a point where we weren't having those meetings so often, even though we were both showing up to the office. I was worried about making the transition to remote, but at some point, I asked myself whether I really need to be in the office all the time.

We mainly communicated through Basecamp just like everyone else who was remote already, but we had this extra possibility to jump into a room together whenever we wanted to. There came a point where we found a new rhythm and didn't need to meet as frequently, so I felt like it could be exciting to move out to the mountains, so I made that jump.

Nowadays, there are a few people who have a habit of coming into the office. Everyone, even if they are at the office, is still communicating with each other through Basecamp at their desks. There isn't a parallel culture of people in the office and people remote, just a few people who happen to be in an office.


"We have library rules at the office"

That's interesting to hear, in the past, we've heard a lot about hybrid teams running into this issue, but you don't feel that at Basecamp?

I think the reason for that is that we always had these library rules at the office. The office wasn't a place where you walked over to somebody's desk and talk to them. It has always been very important for us to really protect everybody's time and attention. If you wanted to socialize and go together to the kitchen and talk, that's normal, but there were never people just chit-chatting standing around their desks. Because of that, it was actually more appropriate to message somebody through Basecamp, even though they're just one desk away from you.

The way that you have a quiet and focused office is by having more asynchronous communication, so it's actually very similar to remote work overall. That was a really great experience, and I really recommend it to people who are transitioning to remote work now. There's this tendency where companies try to emulate the office culture in remote work. They a lot of Zoom meetings and a lot of constant communication in Slack. We always did the opposite. We started with the remote culture and then we modelled our office culture after the remote culture.

You can have some asynchronous back and forth on a clearly defined thread in something like Basecamp. If there comes a point where that doesn't work anymore, then you can escalate to synchronous communication. The point is that you don't start in the conference room, you end in the conference room as the most escalated option.

That transition and moving away from Chicago and the office worked out for you then, I assume?

For me, it was no meaningful change in the way that we were working together. Jason and I couldn't meet in the office to work through something anymore, but now it's happening through Zoom. Then there's the trade-off with not having that sketching together on the wall, but in the big picture, it's a small difference.

It has led me to do more deeper work so that I have more polished work to present when Jason and I do talk. I don't feel like we're going to be able to make as much progress with a blank page together. I try to bring a little bit more structure into it.

I've been experimenting a lot with my tooling for how I sketch and how I share early concepts, which I didn't do before. It was a lot easier to talk something through and then just draw it on the board before. Now, I have Notability on my iPad, where I can just sketch something off the cuff. I've been using Omnigraffle, which is a diagramming tool to share some high-level concepts. There's a lot of opportunities for new tooling in that area. A lot of the software for doing design is too high-fidelity, it just takes too many clicks and steps to manipulate anything, especially if you're doing early concepts.

That's awesome to hear, and will probably spark a lot of new ideas. To wrap things up, where can we learn more about you, Basecamp and your book "Shape Up"?

I'm @rjs on Twitter, my website is feltpresence.com. Shape Up is the book about the way that we do product development at Basecamp, how we put projects together and give them to teams so that they can consistently ship them on time. That's at basecamp.com/shapeup


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