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Shape Up: The Print Edition

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In 2019, Basecamp released Shape Up, a digital book by head of product strategy Ryan Singer about our approach to product development. Since then, Ryan has added sections in response to reader feedback and released a print edition. Ryan comes back on Rework to talk about connecting with other business owners using Shape Up, and how he approached the editing, design, and distribution of the physical book without going through traditional publishing channels.

The Full Transcript:

[00:00:00] Broken By Design by Clip Art plays.

Wailin: [00:00:01] Welcome to Rework, a podcast by Basecamp about the better way to work and run your business. I’m Wailin Wong.

Shaun: [00:00:07] And I’m Shaun Hildner. You know, I think it was about 50 episodes ago, we talked to Basecamp’s head of product strategy, Ryan Singer, about his new digital book called Shape Up. It’s a comprehensive guide to how Basecamp works and covers things like working in six week cycles, thinking about appetites instead of estimates, and Hill charts, which is the way we track progress.

Wailin: [00:00:29] Ryan is back on today’s episode. He’ll give a little Shape Up primer in case you missed the last one. And, more importantly, he’ll talk about releasing a new print edition of Shape Up, which he did after getting a flood of requests for a physical copy. Basecamp’s co founders have published print books before, but Ryan went through a really different process for Shape Up. Here’s Shaun’s conversation with Ryan Singer about the response to his book and how the print edition came into being.

Shaun: [00:01:00] Ryan Singer, welcome back to the show. It’s been a long time since we’ve had you on here.

Ryan: [00:01:04] Hey, yeah, nice to be back.

Shaun: [00:01:05] How have you been holding up?

Ryan: [00:01:07] Things are good.

Shaun: [00:01:08] Good, good. So you just released, by the time this comes out, you will have just released a physical copy of the Shape Up book. Can we get a quick, I know we talked about this on the show before, a quick explanation of what the Shape Up method is?

Ryan: [00:01:24] Yeah. I started at Basecamp 17 years ago. And Jason and David had a lot of really, really juicy, good intuitions about how to do product development. And then as we went from a small team of three, four, five people up to 10 people, up to 30. And now the whole company is what, around 60, I think? We had to go through a period of figuring out how do we actually formalize all the things that we used to sort of do without really knowing what we were doing, other than just kind of knowing that it worked. And also seeing a lot of the same questions come up of friends at other companies around us and our peers saying how is it that you still manage to ship so often? How is it that you manage to keep shipping like you did in the early days? And that’s a problem that I was also hearing from friends who were doing startups. They would be, in the beginning, when they were just a few people, they would ship, ship, ship, and then all of a sudden, one day, they would wake up and they would have a product with customers. And they would feel like it took forever to get anything out the door and forever to make any kind of progress.

[00:02:31] So Shape Up is actually a way to spell out the way that we’ve been doing product development at Basecamp. And put it into a kind of system that other people can understand and then take pieces of that are going to improve their ability to… yeah, basically, to ship work and to have a more energized team that collaborates more.

Shaun: [00:02:51] What are sort of the the key features of the Shape Up method. I’m talking like the six week deadlines, the betting, we can even go into Hill charts, appetite, some of the things that we talk about it a lot at Basecamp that probably need to be defined.

Ryan: [00:03:04] Yeah, I think relative to the way a lot of people are working, the six-week thing can come off as a surprise. It’s so popular now for people to work two weeks at a time. But you can’t get anything meaningful done in two weeks. And six weeks is a period of time where you can actually accomplish a meaningful chunk of work, You can deliver a whole new thing that really works, that actually matters to customers. And then the way that we actually go about thinking about like, what happens inside of that six weeks is very different.

[00:03:33] We talk about appetites instead of estimates. An estimate is where you say, well, what is the thing that we need to do? And then how long is it going to take? And then you schedule that. And we go the opposite direction. Instead of saying, how long is it going to take? We say, well, how much time are we willing to spend? In terms of the value of this thing, strategically, what’s it worth to us? Do we want to spend six weeks on this thing, or less, or more? And then when we first set the appetite, then we have a creative task to actually design the work so that the work is something that can be done within that period of time. So instead of taking the work as a given, and then the time just gets longer and longer and longer, we actually take the time as the thing that we fix up front. And then we kind of change what the work is to fit inside of that. And that’s a that’s a very big difference in approach.

[00:04:28] Shaping, then, is actually the task of figuring out what that work is that’s going to fit into that time box. That we can then give to a team where they’re going to have the creative ability to define their own tasks and work out all the details and make a lot of judgment calls to actually get some version of that thing shipped within that period of time.

Shaun: [00:04:48] So about a year ago, you decided to, or you were tasked with, I’m not entirely sure which one, to distill all of these shaping ideas into a digital book. Can you talk about that process?

Ryan: [00:05:02] Yeah, I mean, I had no intention of writing a book, I had my semi annual review meeting with Jason. Jason told me, you know, I think it’s time for you to write a book about this stuff. It was just around the time when I had started to introduce Hill charts, internally.

Shaun: [00:05:19] Mm hmm.

Ryan: [00:05:20] And Hill charts were a way for us to formalize something that we had been doing just by gut for a long time. And I think that was kind of the last missing piece to really turn this into something that we could share and explain to other people.

[00:05:30] Yeah, so he told me to write the book, I had no idea how to do it. I didn’t know where to start. So I just prototyped it by hosting a one day workshop. Because the thing is, I didn’t know how to write a book, but I was sure that if I had to talk to people for a day that I would come up with something.

[00:05:46] And then this kind of helped me first to do sort of a first sketch of what the content should actually be. And then second of all, it allowed me to actually interview everybody who came to the workshop to learn what were they actually trying to change? What were they hoping to find out by coming to this thing? I felt from the beginning that I could just list out everything that we did. But I didn’t know from the beginning, how to connect it to what other people cared about, and what was important to them. And by doing those interviews, I started to learn, oh, wow. Oh, it’s always the same things coming up. People don’t feel like they have enough time to think strategically about what to do next, because they’re so busy in the weeds with the teams. Or they used to ship quite regularly and now it seems like projects drag on and on, what happened? That kind of a thing. And that allowed me to start to actually frame the book in a way where I felt like it was going to help people make progress.

Shaun: [00:06:41] Mm-hmm. And so when was that published?

Ryan: [00:06:45] Let’s see…

Shaun: [00:06:45] Or when was that made available online?

Ryan: [00:06:48] The very first public version went online in July, I think, of 2019.

Shaun: [00:06:55] Okay, so now we’re talking in October, almost November of 2020. And you’re about to publish a physical copy of this book. I guess, why a physical copy? Why did you feel that that was necessary?

Ryan: [00:07:10] So many people asked for it, that it became clear that just a lot of people wanted it, first off. Which was a really great surprise, because you know, it’s one thing just to hit publish on a website, and then see if you get any traffic. And it’s been really cool, actually, to see the amount of interest. The traffic to the web version of the book has been incredible. I’ve also been hearing from a lot of companies who are actually adopting it. So the interest is really high.

[00:07:37] If we had published this thing as a web book, and it turned out that for some reason, it didn’t resonate, it would have been less of a loss, I think than going through all of this work to fix every typo and polish every little corner and get it into a print version. Having had the web version out for a while, I think we got confident that look, this is something that people are really excited about. This is something there’s interest in, that’s working. This is this is worth the extra effort now.

[00:08:08] Plus, it’s just cool to have a printed version, also.

Shaun: [00:08:11] Yeah, you have a book, right? Absolutely.

Ryan: [00:08:12] [Crosstalk] And I have heard more and more people say that they learn better, and they remember better when they flip through a paper book. And that seems to be true for me, too. There’s something about—

Shaun: [00:08:24] Yeah, same.

Ryan: [00:08:24] —how there’s kind of more information attached to the experience when you’re reading it, that that helps it to lodge into your memory better. And I really like the idea of being able to help people to kind of have a closer relationship with the material and remember it better.

Shaun: [00:08:41] Did you make any substantial changes to the content between—I mean, you’ve been sitting with the digital version, and hearing from readers for a year. Were there any big changes between the digital version that was released in July of last year to the print version now?

Ryan: [00:08:55] Yeah, there were a couple waves of changes. First of all, fortunately, all the sharp-eyed readers of the very, very first version that went up in the first week or two reported a million typos and small errors and stuff like that.

Shaun: [00:09:09] Of course.

Ryan: [00:09:10] So that was that was really cool to get all of that help. So there was a flurry of changes right after launch. And then I posted at the end of the book, if you’ve read this, and you have any questions, or you apply it in your own team, and you would like to reach out, here’s an email address. And I’ve just been getting emails since then with people asking questions. And this has been such a cool mechanism to learn what are the questions that come up over and over and over again. Right away, people started to ask, okay, well, how do you handle bugs? Small issues? How do you deal with things like QA and testing? So I put a small section in that answers that. And then as time went by, the one question that stood out as something that we should have to answer is people kept saying, well, how is this different for a new product versus an existing product?

[00:09:59] Honestly, we had been working on an existing product, on Basecamp, for so long, that I didn’t really feel confident about writing something about how to do a brand new product, because it’s not something that we had done together as a group in a while. And I could certainly come up with things to say about it, but I wanted it to reflect what we actually do, because the rest of the book is very much kind of real and specific. This is what we do. And here’s an example, that kind of a thing.

[00:10:29] And then it turned out, Jason and David kicked off the project to build, HEY, our email service. And this presented a perfect chance to say, okay, well, what was different about HEY. And now that we’re in it, looking at this process of developing the new product, what memories does this trigger? And then, of course, I remembered, oh, I remember what it’s like to be in this phase, where we think we’re gonna do this, but then we end up being surprised that it didn’t work. And then we have to change course. And there’s all this unpredictability in the new product.

[00:11:02] And I had some conversations with Jason and David, we kind of captured a few kind of key points of how working on a new product is different than an existing product, while still plugging all the key points of the rest of the framework in. And so I ended up introducing a section on that. That was actually the last thing before we felt ready to do the print edition that was just maybe, I don’t know, maybe a few months ago, that we added a new section about that.

Shaun: [00:11:27] When we were building BC3, I don’t think a lot of these sort of Shape Up methods were formalized, especially in the way they are now. Was it fun watching all of these now formalized ideas be utilized in the creation of HEY?

Ryan: [00:11:41] Well, I’m still shocked every time I look at a Basecamp project and I see that these things are being followed. In particular, the fact that people are using Hill charts internally continues to amaze me. Like you mentioned, at the beginning of BC3, we were working in cycles, but we hadn’t yet figured out what the right length was. The core notion of having a budget for the time, and then kind of designing the work to fit into the amount of time we want to spend is something that goes all the way back to working with Jason and David on Basecamp Classic in 2004.

[00:12:19] But then, actually, Hill charts, for example, came about because we were in the middle of a project for BC3. And I remember that we got to the end of a cycle, we, by then, were working in the six week cycles. And the work just wasn’t done. We kind of looked at each other and said, Well, how come there were other projects where the work wasn’t done, and we gave it an extra two or three weeks to finish it, and then in this project, the work wasn’t done and we said, we’ve got to scrap this, we can’t we can’t reinvest, we’re not going to give this more time? Like what was the difference? And then I remember one of us said, well, this one never got over the hill. And it’s kind of like, what? Wait a minute, what hill? And it’s like, yeah, you know, when all the problems are solved, and this is kind of like putting the screws in, we never got there, we still had some big unknowns that we didn’t have an answer to, and we’re not going to just put more money and time into something where there’s a big hole in it that we don’t understand, that we never figured out, right?

[00:13:17] The Hill chart came out of that and then I remember prototyping it with Conor and it worked well. And then introducing it to the whole company. And then, to this day, I look and I see, Hill charts with dots flying from one end to the other and it’s amazing.

Shaun: [00:13:33] How was the publishing of this book different than the books that Jason and David have put out, who, sort of, they went through a traditional publishing setup where they would find a publisher, they would get an advance, and that kind of thing. We’re doing this ourselves, right?

Ryan: [00:13:47] Everything was different about this. This, for me, was a really exciting part of the project, because I always felt from the very beginning, this wasn’t going to be pushed by anyone else. There wasn’t going to be a distributor, there wasn’t going to be a book sitting a on a shelf somewhere that somebody was going to accidentally see, just by walking into a bookstore, or at the airport, or something like that. The only way this was going to reach people was if it was so compelling and also useful and resonant that the people who needed it told other people that you got to read this, this is going to change the way you think about stuff.

[00:14:27] That’s why I did that workshop in the very beginning and interviewed people in order to figure out where are those points where it’s going to fit, where it’s going to click in and it’s going to be the thing that actually makes sense to them and they’re going to say, wow, this really helps me.

[00:14:44] We did everything ourselves for Shape Up. I just wrote it. We didn’t even have an editor or we didn’t even have anybody to proofread for typos. Adam, who is our, I don’t know what you call him because he has so many skills. He’s kind of our marketing designer, so he’s not working on the applications ,but he’s working more on the marketing websites and stuff like that. But he’s also very skilled web designer and graphic designer and print designer. And he’s also very technically accomplished. So he actually designed and kind of custom built the back end, to convert all of the book files into a web book that had all kinds of nice navigation features and rendered everywhere in a beautiful way, and was very maintainable and easy for me to keep shipping changes to. So this was it. Basically the whole production side of it really was Adam.

[00:15:36] So he built the website, we shipped it as a website. And then the time came, of okay, how do we do a book? One constraint on us, from very early was that actually Jason and David didn’t want to sell on Amazon. It’s the place, if you were to publish your book, you’d think you would want to be there. And they said, no, look, we want to do this ourselves. So Adam designed the print layout. He did everything from the cover to the spacing of words, so that the flow of words across pages would look good. Reformatted everything. He also made all the choices about paper and stuff like that. And we ended up with a beautiful, perfect bound, full color book, thanks to his design work.

[00:16:16] And then he set up, we have an online store where fans of Basecamp can buy stickers and stuff like that. And then, and then he extended that, to to offer the book there as a product on the store. And that’s where we’re selling the physical books today is through our own online store.

Shaun: [00:16:33] Yeah. And we’ll link to that in the show notes. It is a really cool looking book. I’m on the website right now. Especially because all the illustrations in the book, are sort of of a specific style. Did you draw those, or are those Adam as well?

Ryan: [00:16:47] Yeah, I actually drew all the illustrations on the on the iPad.

Shaun: [00:16:51] They look really great in print.

Ryan: [00:16:52] This was such a cool kind of happy accident. So the the iPad app that I use is called Notability. And it turns out that whatever you draw in there kind of gets converted to vector format. So it’s like infinite resolution. So I was able to export all of the original drawings from the digital book as PDF files with perfect resolution, and now they look crazy sharp in print. And I’m super pleased with how that worked out.

Shaun: [00:17:19] And you’ve also been doing sort of these live Q&As these live sessions with people in our industry that have been using the Shape Up method to ship real work. How’s that been going?

Ryan: [00:17:32] That’s been really interesting. That actually started because in the beginning, I was doing one on one video calls with people who wrote me and asked me for advice or to answer questions, because I just wanted to learn. I wanted to learn, what were they trying to do? What was happening in their team? Why were they even trying to use this method, all of that. And so it was kind of a win-win at first to do these one by one.

[00:17:55] And then what happened was, I was getting so many requests that I realized that I wasn’t going to be able to do my day job anymore, if I just kept having calls with people about Shape Up. So I thought, okay, well, how about, we could set up kind of a win-win, where if we do it in public, more people will be able to see the questions and the answers and it’ll promote the book. And it’ll also kind of naturally filter people, because not everybody is willing to go online to do a live stream.

[00:18:22] And I’ve been really happy with these. We’ve done four now. And basically, the first half is me getting the background on the company, which I have to do in order to answer any questions or give any recommendations to understand where they’re coming from. But it’s also a cool way to hear about the journey that companies go through as they’re growing and figuring out how to go from 5 people to 15 people. Or what do they do when something changes in their business model, and now they have more customers, they have to serve at the same time. Or all kinds of different things happen. It’s been amazing.

[00:18:52] So I’ve been able to learn a lot about what’s going on at different people’s companies, and then also really answer questions with a lot of context. And it helps me, too. Slowly, I’m building up an understanding of what some kind of either, at least at a minimum, how to answer these questions better when they come up, because I’ve worked through them with more people. And also, maybe they become some kind of future edition, or some future book or who knows what, you know.

Shaun: [00:19:20] Yeah.

Ryan: [00:19:22] So it’s been it’s been an awesome learning process on both sides.

Shaun: [00:19:25] Do you have any fun examples of the sort of companies and problems that are being solved that have been using Shape Up?

Ryan: [00:19:32] I think a really great one is Adam Wathan at Tailwind CSS. He, and I think maybe a co founder created this kind of CSS library for web developers, that makes it much easier for them to manage the way that they style the webpages. And this thing completely took off as an open source offering. And they had the idea to start a business around it where they would kind of create components that solved harder problems, so you could kind of buy something off the shelf instead of having to build it from scratch. And he just wrote me an email saying, look, the amount of stuff that we have accomplished in the first six weeks was just mind blowing. And that’s the kind of email that I keep getting, is like, wow, we did a cycle and I can’t believe how much we can get done in six weeks when we work this way. And the team is way more energized before. So that’s, that’s been really exciting to hear.

[00:20:22] The other thing that’s kind of really surprised me is that there’s there’s actually a Fortune 50 company that adopted Shape Up for their digital teams.

Shaun: [00:20:29] Oh, cool.

Ryan: [00:20:31] And I never anticipated that you could use these methods in such a big corporate environment. But it turns out, they have all the same problems. And it’s all kind of the same basic issues again and again. And they’ve reported amazing success there. So, we’ll continue to share some case studies here and there as we can, but it’s been amazing to see what people are doing.

[00:20:53] Broken By Design by Clip Art plays in the background.

Shaun: [00:20:53] Awesome. Well, Ryan, this is fantastic. It’s great to see your face and hear your voice. It’s been a really long time.

Ryan: [00:20:59] I know it’s been much too long. I guess we have a virtual meetup happening November, so that’ll be interesting.

Wailin: [00:21:09] Rework is produced by Shaun Hildner, and me, Wailin Wong. Music for the show is by Clip Art.

Shaun: [00:21:14] You can buy your very own copy of Shape Up at There you’ll also find the full digital version and links to other conversations with Ryan, and his Shape Up live recordings.

Wailin: [00:21:26] Ryan is on Twitter at @RJS. We are on Twitter at @ReworkPodcast, and you can always find us on the web at