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May 15, 2023, 6 a.m.
How Ryan Singer Uses OmniGraffle

Ryan Singer is one of the founding members of 37Signal’s Basecamp team. Today, Ryan's consulting company, Felt Presence, helps people solve problems between their product and engineering teams. He credits OmniGraffle for being his brainstorming partner each step along the way.

Show Notes:

On this episode, we find out how Ryan's design, programming, and strategy experience led to an innovative approach (and book), called “Shape up,” to bridge the gap between product and technical teams. Tune in and learn how Ryan's OmniGraffle expertise contributed to his success and how "Shape Up" helps humanize the software development process and ensure team projects get successfully completed.

Some other people, places, and things mentioned in this episode:

- A shorthand for designing UI flows
- Breadboarding in Shape Up
- Small tools for shaping
- Shaping in a Nutshell
- Felt Pesence
- Shaping in Real Life course
- Bob Moesta
- OmniGraffle
- Miro
- OmniFocus
- Mailchimp
- Convertkit
- Hey
- Remix
- Netlify
- Whimsical
- Basecamp


Andrew J. Mason: You are listening to the Omni Show where we connect with the amazing communities surrounding the Omni Group's award-winning products. My name is Andrew J. Mason. And today, we have Ryan Singer sharing how he uses OmniGraffle. Well, hey there, and welcome to another episode of the Omni Show. My name is Andrew J. Mason. And today, we are so excited to be able to have Ryan Singer with us. Ryan Singer is one of the original team of three that helped launch Basecamp at 37 Signals. His work has deeply influenced the software as a service industry, and more recently, over the last 17 years, he's helped design processes that teams use to design, develop, and ship software. We'll talk more about that. Over time, Ryan's role has evolved from UI designer to product manager, to now head of strategy. And in 2019, Ryan wrote a book about managing software development called Shape Up: Stop Running in Circles and Ship Work that Matters. Ryan, thank you so much for hanging out with us today.

Ryan Singer: Yeah. Thanks a lot, and I'll just mention that in the last of couple years also I've been working independently under Felt Presence doing consulting to help companies to implement Shape Up and to solve problems between their products and engineering teams.

Andrew J. Mason: Thank you for mentioning that. Very cool. And let's talk about that. How do you end up in a career path where this is now your life? It's such a broad question, but just wondering, can you give us a sense of was this more intentional or did you take each next step to see where it led?

Ryan Singer: It's been a constant I come into one area, try to do what I can and then find the edges of how much I can contribute, and then I find myself in a new area over and over again. So I started just being interested in web design in the '90s, when the web was new and I couldn't really program even though I was really into computers since I was a kid. So I got into making webpages because it wasn't that hard to do, and I got into user interface design and then I reached a point where I couldn't really get far enough because I could design what I wanted the software to do, but I couldn't actually make it do it. So I realized that I needed to learn how to program. So then I got into programming. And then I knew both of these worlds, the world of the programmer and the world of the designer. So that put me in a position where I could be the person in between these different teams, and speak both languages. Then I was getting into product management and being the bridge between design and development, but then, the question started to come up of, "Well, okay, now that I can work between these two worlds, what's actually important to do? What's actually valuable to do?" So then I started learning about strategy and business, and how to understand the demand side of what people want and the supply side of what we can build and how those things go together. And that's how I ended up getting more into strategy. And then along the way, the whole time I was at Basecamp, the company was growing and changing and there were new challenges appearing, and things that we were doing just intuitively, organically as three people, five people, 10 people. There came a point when we were 20 people, 30 people, 50 people, and it wasn't possible for it to just happen automatically anymore. We had to formalize and figure out how to define the things that we were doing that were working so well for us, and that became Shape Up. And then much to my surprise actually, Shape Up has really spread a lot through the software industry and I'm hearing from people all the time who either tell me, "We've been doing Shape Up for four months now and it's great." Or, "We've been doing Shape Up for a year now, and it's been amazing." And I also hear from a lot of people who say, "We're trying to do it and we can't figure out how to adapt it exactly to our situation." Those are cases where I get in there and I actually learn about all the places where the exact way that we were doing it at Basecamp doesn't exactly fit to what's going on in other companies that are structured differently or have different needs. And so, I've been in this kind of big learning process over the last couple of years of adapting it and learning how to help more companies do it, and that's led into new things. So then it's like, "Okay, I wrote the book and people are using it." But now, my wife and I recently made an online course to help companies who are not structured like Basecamp to use stuff from Shape Up. And then it's like, "How do we make a course?" You don't have to learn all these other new things. How do we do the video? How do we edit it? How do we put it onto a course platform? How do we do all these things? It's always a learning process just to overcome the next challenge.

Andrew J. Mason: Hey, the humility, just to say, I don't have it all figured out and I'm just taking each next step as it shows up. That's great.

Ryan Singer: Well, I tell you every time I start to think that I have it figured out, that's when it starts to get stiff and boring feeling. You know what I mean? It's less fun to talk to other people because I think I have all the answers. And when you're really starting to struggle with something and you're like, "How am I going to get through this? How am I going to make this work?" Then a lot of things come to life. That's really an exciting place to be.

Andrew J. Mason: Well, hey, I do want to honor that you're here for OmniGraffle, but before we dive in, talk to us a little bit more, give us a few more sentences about Shape Up. What is that process and how do people tell whether or not it's something that they'd like to engage with?

Ryan Singer: So when it comes to figuring out how the designers in a software company, how the product people in the software company work together with the technical people and the business people, there aren't a lot of clear answers out there. A lot of people use things like you maybe heard of Agile or Scrum, or Sprints, or doing things like that. And those things are methods to manage the tickets of work, the pieces of work that people have decided should happen, and then figuring out how to make sure those little pieces of work get done. There's a lot of systems out there for doing things like that and a lot of famous software packages like Jira and Kanban Tools, there's a million things for how do we make sure that the little pieces of work, the assignments they actually get done. The question is that how do you actually figure out what it is that we should be doing? And how do you actually bridge that gap where the product people have an idea of what they think we should do, but they don't really know what's technically possible? And the technical people know better what's possible, but they don't necessarily understand the customer. So you have this big disconnect. And so, when we talk about shaping, we talk about this step in the project formation where the people who understand the problem that we're trying to solve for a customer, the project that we're trying to put together, how they actually get together with the technical people to come up with the approach of this is the thing that we think we can go build. So we call that shaping. And if this was the software development podcast, I could talk about a whole lot of other details and stuff like that. But broadly speaking, the big difference there is a lot of people in the industry who've heard about Agile, they have this idea that you cannot plan anything upfront and you can only decide things as you go along the way. And what you find out is that a lot of surprises come up. Things turn out to be more complicated than you thought. Things turn out to be harder than you thought. Things that you thought were possible turn out to not be possible. And actually, it's much better to know those things further upfront. So instead of just saying, "We're going to figure out as we go." Shape Up is a way that you can put heads together and actually look at the unknowns and surface some of those time bombs that would otherwise explode later so that you can have a clearer approach and more confidence that you're actually going to be able to ship something in the next three weeks, in the next six weeks or however you set that time box that you need to be finished in. It's really helping teams to actually finish work and not just be on this treadmill where it's always two further weeks away.

Andrew J. Mason: What a novel concept. I think sometimes those of us that are a little bit more technically minded become beholden to a process at the expense of humanity. And it sounds like this really introduces the humanity slice back into the entire thing or even just throws that clear thinking back into the process to begin with. I guess that's what I'm saying.

Ryan Singer: That's a great way to put it because it can become so mechanical. Put the task into the box and then feed it into the machine, and then everything is going to come out right. But the harder parts are actually putting our heads together to understand what are we actually trying to do here? What does it mean for us to be done? How will we know when we're done? Is this really a good approach or not? What other approaches could we take? Those things they have to somehow get figured out and we need a little bit of structure to figure out how we actually bring people together to solve those questions.

Andrew J. Mason: Well said. Well said. And talk to me about your first encounter, if you have a memory of that or any first thoughts or ideas of when you came across the Omni Group or OmniGraffle.

Ryan Singer: Yeah, I'm probably going to overstate it, but in my rough idea, I probably first tried OmniGraffle 20 years ago. I don't even know if it existed 20 years ago, maybe 15 years ago, 12 years ago. I don't know what the real number is, but a long time ago. I can remember being in the office, the first office that I worked out of when I joined 37 Signals and I had my computer there and it was a Mac, I went into the office every day, which is not the case anymore. For many of us that's changed, right? So many things have changed in the last 10, 15 years, and I remember trying out different Mac software all the time. It was also before there were a lot of web-based tools. It was certainly before the wave of online whiteboarding tools like Miro and stuff like that. So I can remember I probably installed OmniGraffle all those years back because I was always trying to communicate visual ideas. And I was always learning, trying to figure out which tools were going to work for me, and it was somehow in the rotation of things that I knew about. I remember also I used to OmniFocus for a while back in the day, so I knew about Omni, I had this sense that Omni was one of those companies that somehow they're a brand in my mind that it's like a real... I don't know what this means, but it's like a real software company. There's all of these little apps that you download and it's like one person made them and sometimes they're great, but a lot of the times, there's a lot of corners cut and there's a lot of things missing, but Omni's been around for a long time and they have the suite of apps. And especially for me as a web designer and somebody who basically learned a program doing web stuff, I always was really impressed when there was a software company that made a Mac app that you download. I was like, "Whoa, that seems hard." Or how do you actually make something that you can draw in, that's so much harder than just saving some information you type into a box, into a database. That always really impressed me. Yeah. So I've known about it for a long time and it's really in the last, I think, less than two years that I came back to OmniGraffle and it became my regular go-to. Already maybe four years ago I started using it a little bit more again, but really especially it took over in the last couple of years where it's one of the main things I reached for these days.

Andrew J. Mason: Man, I would love for you to share the last two to four years. What are some of those use cases or specific examples of how you might go about using OmniGraffle?

Ryan Singer: So there was a time when my work was more just about coming up with an idea for how a piece of software should look, imagining the interface, where the buttons are going to be and how you're going to get from A to B to C, and I needed some tool where I could. There's the drawing tools where you actually try to make a picture of this is what the design is going to look like and that's where people use things like Figma today or back in those days I was using Photoshop to do that, but there were other times when you needed to just diagram out the bigger idea of there's going to be some screen, and I don't know what it's going to look like and it's going to have a button like this on it, and then when you click that button, it's going to take you to this other place. So just diagramming the flow of things. I would occasionally reach for OmniGraffle when I needed to make one of these diagrams. I actually wrote an article called A Shorthand for UI Flows, something like that. You can Google it and it's on the old 37 Signals blog. And you'll see some examples there of this technique that in Shape Up, it's called breadboarding, and it's just a notation technique for how to quickly draw a flow in a user interface. And when I was doing really simple breadboards, I would just sketch them by hand on a piece of paper, but if I needed to share them with the team or if it started to get complicated and I had really a lot of steps in a lot of states, then I would open up OmniGraffle to make it because I didn't know any better tool, I didn't know any other tool to use. So that was already maybe 10 years ago, and if you look at that article, you'll even see what looks like some computer made diagrams alongside the hand drawn ones, and those were made in OmniGraffle. And what I found was that as my work shifted from designing what a button should look like and designing what the pixels and colors on a screen should look like to more strategic questions of what are the different possibilities of how this thing could work, what are the different architectural pieces of it? And also, as I started doing more research projects, I got into a situation where I needed something that could help me think the way that you use a whiteboard. If you're trying to think through a problem and you've got two or three people in a room and you're really, it's not like a meeting, but you're actually jamming like, "Maybe we could do this. What about this? Let's try this." You're drawing on the whiteboard and you're sketching out ideas and you have boxes and arrows and this kind of a thing. And what I found was that I just was trying to solve a lot of really hard problems and I needed to be able to whiteboard with myself. And what I started to notice was that if I drew things on a whiteboard, it just didn't let me experiment fast enough because it takes a while to write things out by hand. I can type faster than I can write with my hands. If I wanted to quickly copy and paste something and then change one thing and have, "Here's version A, here's version B with a slight tweak to it," rewriting everything on a whiteboard, again, it's just slow and not really satisfying, but if I'm doing it on in a tool like OmniGraffle, I can just copy and paste a whole diagram or a few random boxes that I drew and be like, "Here's the duplicate version where I change one thing." The way that I think about this a lot is if you watch the way that a graphic designer works, somebody who makes logos or somebody who makes icons, or something like that, and you look at any YouTube video of a graphic designer working or you look over the shoulder, if you know somebody and let's say they're designing an icon, they are going to have 20 versions of that icon on the same screen. They keep copy paste, copy paste, copy paste, and then like, "What if this is blue? What if this line is thicker? What if I reverse this? What if I move this to the other side?" And there's like a million versions as they're exploring to figure out what is the right thing. That's basically what I'm doing at OmniGraffle. It's the place where I can go to try out a lot of ideas. If I'm coding, I'm coding. If I'm designing and I'm actually trying to make a design that I'm in a design tool, but there's a lot of work that isn't the hands dirty down in the weeds actually moving pixels around or writing lines of code work. There's the figuring out what am I going to do work, figuring out my approach this work. Whenever I have that work, which is I actually think all the time, I think this is a underappreciated kind of work, the thinking work of how am I going to go about doing this? And then I go into OmniGraffle because that's a place where I can... Yeah, it's a super whiteboard or I can just put everything there and I can easily play with different ideas. I've got a project going right now. I have some articles that are on one platform. I have an email newsletter on another platform. I have a website that I hacked together and hand coded, and I'm doing some marketing for this new shaping and real life course, and I started to learn from people that a bunch of people were reading an article of mine. It's on a platform where I have no way to track how many people are going to that article. I can't count the views of how many people look at that article on the platform it's on. So I'm starting to think to myself, "Maybe I need to rethink how I do my blog and my website, and my email so that I can start tracking things better and I can know what gets more traffic and I can have more intelligence about stuff like that. So this is an example of a real life problem, and what I need to do is I need to figure out, "Well, what do I have today? And what's working, what's not working and what might a new system look like?" So I literally, just this morning, opened up OmniGraffle, and I have this template style. It's a little bit like a sticky note where it expands as I type it and it's the nice little box with a little shadow on it, and it's just a little box and I can type something in it, and I just copy and paste these things and I have a million of these boxes. First, I make a frame, so I have a white box with a gray line container, and this is the empty space where all the things that I have in my current solution are going to go, and then I make these little sticky notes inside and it's like, "What do I have today?" Okay, my articles are on a platform called Hey World. My email audience is also on Hey World. In addition, I have MailChimp for email. I have a hand coded website. I have some of the articles are also hand coded on the website. Plausible is my event tracker that I'm using to know how many hits I get on the website, like blah, blah, blah. And I'm looking at, here's all the stuff that I have. So now, okay, this is the current system and this is where it's hosted and I don't have a CMS and blah, blah, blah. This is my current system. Now, I've got another thinking problem, which is, "What am I actually trying to change here? How will I know if the solution..." So basically I'm shaping. "How will I know if this is better? So what am I actually going to do differently and how will I know it's better?" I have a different thinking tool where I make four more of these big container boxes for the four forces that are in my decision-making process, "What's pushing me, what's wrong with what I have today? What's pulling me? What am I hoping that I could do differently? What are the habits? What are the things that I don't want to lose that I don't want to give up if I change something? And what are the anxieties that are the unanswered questions?" I literally create these four boxes, push, pull, habit and anxiety, and I'm sticking sticky notes in them. What's wrong today? I noticed that I'm not posting articles as much as I was before because I realized that every time I post an article, it's going somewhere where I don't get any analytics on it. I don't want to do that anymore. I want to be posting on something new. I realize, "Okay, in the poll box I put a sticky saying, I want to be able to know which articles are popular. In the push box, I realize people keep telling me that some of my old articles are things that they're reading and I have no idea how many. In my habit box, I can currently post really quickly and easily on hey, and it looks great." I really like how it looks and I love how fast it is and I don't want to give up that it's fast and it looks good, but my anxieties are like, "Is it going to be too much work to set up my own blog? Is the blog going to interoperate with my email notifications? How am I going to solve that? Are my articles going to look ugly because I really like the typography on Hey, and I'm not a very good designer?" I'm looking at it right now. I've got one, two, three, four, five, six, seven or eight sticky notes in these different boxes that help me to figure out what's wrong and what I'm trying to solve. So now what I'm thinking is, "Am I going to go buy a CMS to do this? Am I going to change from MailChimp to ConvertKit because I could better customize my email templates? Am I going to move my website from the current host to something more modern, versatile or whatever where I can do some custom thing? Am I going to code it in remix instead of doing it hand coded?" I've got all these different thoughts now, but what I might do differently, so all these things I'm throwing on here as stickies, and then the place where I can start to get some order out of this is I can have another container box for my sticky notes and OmniGraffle, I can have a container box, which is like path A, I move to a commercial CMS that does all this stuff for me that makes it look good and also handles the emails and is also going to give me the analytics I want. Option B, I build this myself using Remix and I deploy it on Netlify and I'm going to use ConvertKit to integrate the email part. These different options are appearing, and I'm not getting lost in the weeds of trying to actually code something. I'm not on the website of Remix trying to figure out what exactly my framework is going to look like. I'm on this higher level where I'm figuring out all my options. It's like when you're shopping for a car, you've got three different things you're looking at and you don't know what you want, and you're trying to figure out what trade-offs you're willing to make. It's like that thinking process. And the other thing too is maybe when I had a fixed base, I might have done something like this on a whiteboard, but I am moving around all the time and my laptop is really the home of everything that I do, and it's much better for me to be able to quickly open up my laptop and then I can pull up one of these just documents in OmniGraffle, which is really this giant whiteboard and everything that I'm working on to figure out what to do next on a problem gets all there with me, and it's offline. If I'm on the plane, I travel all the time. My wife and I are digital nomads, and sometimes my local SIM card stops working and I don't know how to get to the local place... It's like I am not going to have internet for the next six hours until I figure out how to get this thing topped up at the... And I don't speak a language or whatever, so offline happens. I don't have to worry that it's not going to load when I quickly have an idea or there's something that I need to be able to look at in order to make a decision.

Andrew J. Mason: Dang, Ryan, thank you so much for sharing that. It honestly sparked so many thoughts for me. I don't want to break flow, but, man, just made me think about David Allen's, he had something called the Natural Planning Model, and somewhere around step three there was something called the How, and How was broken up into two parts, and there was this divergent part A where it's just about creativity and possibilities, and just breaking off in all the million different possibilities and thoughts that you can have for brainstorming. And then at some point there's just this natural transition. You just know when it's time to go into part B where you start to collect and gather all of those different possibilities and say, "Okay, I'm not planning on officially doing any of these." Like you were saying, I'm not necessarily going into ConvertKit right now, but I'm gathering these and thinking about what components could form together into an actual process. What I hadn't thought about before is using OmniGraffle as this repeatable, replicatable space of thinking saying, "Let's try process A with a variation, copy and paste." Know how about process B, which is really just process A with a tweak to it. Now, you're able to look at multiple paths of logic in a visual way. That is cool.

Ryan Singer: If there's one thing that I'm doing constantly in OmniGraffle, it's like copy and pasting things side by side so that I have option A, option B, option C, because I just can't do it anywhere else. I even do a lot of my writing in OmniGraffle now, which is ridiculous because it's really pushing it to the edge of what it's good at. But the thing is, if I open up a text document or pages or Word, or whatever, Google docs, I only have one flow of text. There's no version B. If I have got an outline for a talk I'm going to give, I'm going to give a presentation and I think I'm going to talk about 0.1, 0.2, 0.3, 0.4, and these are the bullets of the things I think I'm going to talk about. I will literally just stack those up as stickies in OmniGraffle, a big column of stickies of the points that I think I'm going to hit in this talk, and then I'm going to look at that and I'm going to be like, "That's not right." And I don't want to lose the work that I did and I want to be able to try a different like, "What if I start off with a case study instead of starting off with the principles in this talk?" Right? Or, "What if I open up by talking about the struggling moment or whatever?" I have different ideas for how to sequence the talk that I'm going to give, so then I can just literally copy and paste all those stickies and just drag them around into a different order, type new ones in, delete some of them, and now I have a different outline for a talk and they're both there. If I'm in a text document, I can't do that. I can copy and paste and then paste underneath, but you can't see it all side by side, and you can't like I'm very visual. I need to see everything in order to understand where I am and what I can do. And so, the other thing too is that when I'm an OmniGraffle, I am always out at 50%, 25%, 10% zoom with a million things on the screen, and then I'm diving into one area. If I think, "Okay, here's another option for how I can reorder this talk or what are the points I might need to talk about in this talk." But then I can zoom out again if I think I liked my first idea better.

Andrew J. Mason: Man. Sorry, you're blowing my mind a little bit. I haven't thought about this before, where you take something sequential like text, zoom out from it and say, "Okay, now, OmniGraffle is my space to be able to look at this in a more associative visual way." And then you manipulate it outside of the sequence.

Ryan Singer: Just like a graphic designer, it's just like the graphic designer working on the icon. How come the graphic designer can have 10 versions of the icon, but I can't have 10 versions of my talk?

Andrew J. Mason: Ryan, these are some really good use cases.

Ryan Singer: The other thing that really brought me into OmniGraffle more heavily recently is I've been learning a lot of these thinking tools. So my friend Bob Moesta taught me a lot of these things. They're things that he taught me how to do on a whiteboard. So for example, if I have a project and I've got 10 different steps, let's say, I'm going to go build my new version of Felt Presence, my website, and I've got this new version of the system I'm going to do, right? The new host, the new CMS system, the new email thing, what do I do first? Where do I start? Even if I think I know what to do? Do I go to ConvertKit first? Do I go set up net Netlify first? Do I start hacking in Remix? Do I do a wire frame design of what the new layout looks like? Where do I even begin, right? I've done a couple articles about it, so maybe we could reference something in the show notes if you like, but it's called the Interrelationship Diagram. And it's a way of you take the, let's say there's 10 things that you know have to do. You arrange them in a circle and then you take them one by one and you say, "If I do this thing, does it help me then to do any of the other things afterward?" And you draw an arrow to the other thing if it helps you to do the other thing, and you go around the circle like that, and what you get is this graph of arrows that basically shows you which things help you do, which other things. And then you can literally just do some... You can count which ones have more arrows going out versus in. Or I even have a technique that I do an OmniGraffle where I literally... Because it's all connected because of the magnets and the connections of the lines, I just drag it all off the circle into a format where I can see the which thing basically has all the things hanging off of it and then which things come next. And it literally shows me like, "You need to do this thing first because all the other things are going to be following from that." Versus this other thing you can do last because it's not going to help you to do any of the other things earlier. It's showing the interdependencies. That's a tool where if I know how to do that, I can take something and I can run it through interrelationship. There's no piece of software that you can download to do that. And so, what I needed was like, "Well, what software can I use as the platform that I use to do this?" And I've tried a lot, and so far, OmniGraffle is the thing that I keep coming back to and I have a handful of different tools that are like that. We talked about one, this thing about the four forces. Also my friend Bob Moesta, he has this whole framework called Jobs to Be Done, and inside of that, one of the main techniques of understanding why somebody is trying to make a change and why they're changing their behavior is these four forces, and I can make a four forces diagram in OmniGraffle and I can move stickies around to figure out what's going on and to get clarity around a situation where there's some decision-making happening. So there's a lot of these different tools and the more that I started to make these tools part of how I work, the more I needed something, let's say, on my computer where I could do these in a fast way and I could basically make these and change them, and also collaborate with other people on them. I can't just walk around with a giant whiteboard all the time and take photos of it. You know what I mean? So there's got to be something else. I've used Miro and Whimsical, and I've used a lot of those online whiteboarding tools, but it's interesting because on the one hand, they can be a better choice when I need other people to be able to collaborate with me, but I actually think that this live collaboration is really overrated today. There's a big push where everyone is trying to enable people to work on the same document in real time, and I actually think that the thinking time where you work on a document and then you get to a point where you reach a conclusion, and then you share your conclusion with people and then you discuss where you got to and then you have a different session and just one person, you have moments when you're changing everything and other moments when you're more just presenting things. I actually think that this tends to work out better than everything is always real time and editable all the time. I'm actually quite happy to run a Zoom call, and OmniGraffle is open and somebody is driving. Just like with a whiteboard, it's like somebody is driving, and I would rather that we are talking together about what I'm typing in this box as opposed to everybody is just typing all at the same time or something like that. I don't think this thing of everybody typing at the same time is a real use case. I think it's something that the software people invented that isn't really a big win when you're actually in a creative situation and you're trying to work together. I might be overstating that. There probably are cases, but I don't think it's the main case that we all need to be editing and simultaneously and stuff like that. So in a lot of cases, I'm actually okay with something that doesn't have that real time factor. I hoped that when I tried a tool like Miro or Whimsical that because... There's a lot of really great things about those tools. One of the things that's an advantage in those tools is that they have fewer settings on everything. So in a way, the defaults are more just what you want. I've seen a lot of people open up mural and they can very easily just start creating sticky notes, and this isn't a criticism of OmniGraffle, this is just, I think a trade-off. It's harder for me to make a sticky note that automatically looks good in any size, and without doing any configuration of font and wrapping, and dragging the edges. It's a little bit harder to get a great looking sticky note in OmniGraffle. So for a while, I thought that I should be doing this stuff in Miro because I'm mainly just moving sticky notes around in these different boxes. But what I started to find is that as soon as what I needed was beyond the standard sticky note, the capability of these other apps fell off a cliff and I would find myself back in OmniGraffle because I could actually make it what I wanted it to be, because I had all the controls, you know what I mean? So it's this interesting tension of how much control do I need versus how fast are the defaults? And in the end, I ended up breaking that trade-off by creating these custom styles in OmniGraffle that have the behaviors that I want so that I can basically create what I want. I am honestly fussing with it a little bit more than if I was in something like Miro, but I'm willing to make the trade-off because I prefer having the offline access. I like being able to fine tune things better. I find that being able to zoom in and out and stuff like that tend to have a little bit more control over that. The trackpad is more reliable in an offline app than it is in Safari for some reason, for pinching and zooming. There are times when I'm in a tool like Miro or Whimsical, I'm pinching to zoom, and then all of a sudden the Safari will move me back to some other page. It didn't know that I was just trying to zoom or I don't know what happened, but I feel like when I'm in a real app that I don't have those problems as much. So there's a lot of different trade-offs to be, but I just love the fact that I can work on these tools and I can prototype these different thinking tools because I have enough of the controls that I need to actually make them. It's like, I don't know, my little workshop of whiteboarding tricks to solve all these thinking problems.

Andrew J. Mason: Man, Ryan, I so appreciate your time with us and hanging out with us. One more question. When it comes to your career and finding out all the different ways that you can attack problem solving, is there anything that you look at and you say, "You know what? I thought that was going to bear fruit. I thought that was going to be a really great way of doing this, and it just didn't pan out for me." So you learn from my experience, have some lessons learned and just don't necessarily do it the way that I did it.

Ryan Singer: Yeah. One of the things that was a really big lesson for me is for many, many years I thought that if I could come up with the right answer... First of all, I thought that there was whatever it is. Let's say, I'm working with another team on a software product, or we're working on a marketing idea, or we're working on a strategy idea for the business, whatever it is, my view in the past was like, there is a right answer, and if I can get to the right answer by hard work and just fighting, wrestling with the problem, and I get to that right answer, I should be able to just go to other people and say, "Here, look, clearly this is the best answer." And everyone will be happy about it and appreciate it as being the best, and that's what matters the most. What I was really undervaluing is there's a whole human side to that. My definition of the right answer depends very much on the things that I consider to be important and the things that I'm willing to trade off and say, "That's not so important to me." If we were trying to agree on where to go for dinner, maybe one of us would say like, "The most important thing is the atmosphere." And another one of us would say, "The most important thing is the budget, because I promised myself I wouldn't spend more than X dollars on restaurants this month." And if one of us is thinking about atmosphere and the other one is thinking about budget, we are going to have very different definitions of what the best solution is. And in order to actually work together and come up with something that's meaningful for everybody, there's way more back and forth that needs to happen in a collaborative way between us as people where we need to talk about, "Well, what's wrong with this option? And what if we were to do that option? And how can we judge if we're making progress or not?" So figuring out, this is a long answer, but what I'm trying to say is that what I understood is it's not just like math on the whiteboard of getting to the perfect rigorous solution, and then everyone should appreciate it, but it's really about understanding what's important to people and how everybody has something else that's important to them, and going through a process of really talking with each other and collaborating with each other to figure out to bring everyone together through the process of the decision-making. So really leaning more into the fact that not only is there not one answer, but also figuring out how to really connect on a human level with the other people who are involved to better understand everybody's role in it.

Andrew J. Mason: Ryan, such a great conversation with me on a selfish level, and I know also with all of our listeners just different ways of thinking about how they can be problem solving. I think it's really, really useful. How can folks find out more about what you're up to?

Ryan Singer: Yeah, so you'll find me on LinkedIn, I'm on Twitter, and if you go to, maybe the website will change, but you'll find all my work there. You'll find a nice introductory video to the principles of Shape Up. There's a 20-minute intro video there called Shaping in a Nutshell. You'll find info about that course that I mentioned called Shaping in Real Life, which is how to use these different principles with a team, and especially a team that isn't exactly like Basecamp, structured the same. And of course, you can also find the original Shape Up book that I wrote when I was at Basecamp, which has a lot of the principles, and it also has the specific practices we use that worked in a company that was structured exactly like that. Plus articles and the other things I'm doing. You can find all that at the website at

Andrew J. Mason: That is incredible. Thank you so much, Ryan.

Ryan Singer: I really enjoyed it. Thanks a lot.

Andrew J. Mason: Hey, and thank all of you for listening today too. You can find us on Mastodon at the Omni Show at You can also find out everything that's happening with the Omni Group at