How to Make Design Decisions - Tyson Rosage24:47 with Nick Pettit
Tyson Rosage is a designer at Treehouse. He works on the Treehouse application and helps members navigate content by designing intuitive user interfaces. Previously, he was a designer at Digg. In this interview, Nick Pettit talks to Tyson about career development, reaching a consensus on design disagreements, and more.
[Treehouse Friends] All right. Well, Tyson, thanks so much for hanging out with us. 0:00 For people who don't know who you are, 0:04 who are you, and what do you do? 0:06 [Tyson Rosage] My name is Tyson Rosage. I'm a designer at Treehouse. 0:08 Mostly, what I primarily work on is designing the user interface 0:15 and develop the product flow for how people navigate all our content. 0:20 [Nick Pettit] That's awesome. So let's back up and start at the very beginning. 0:26 Where did you first grow up? 0:31 [Rosage] I grew up in Olympia, Washington. I've always been directed towards art stuff. 0:33 I guess that's kind of--most people who got into doing design 0:39 came from that type of background. 0:44 I was very much into music, playing guitar and playing in bands, 0:46 and that was my gateway into doing stuff for the Web, 0:50 which was, we needed a website at the time, 0:57 and that was something that I took upon myself to figure out how to do 0:59 and developed that over the years into now being my career. 1:03 [Pettit] So when was that, that you first got into it? 1:07 [Rosage] I actually got into computers very late, relative to a lot of people. 1:10 I don't think I really got into it seriously until like my senior year of high school, 1:15 and then I got very obsessive about it in my first few years of college. 1:21 So much so that I didn't finish college, because I had spent a lot of time in college 1:26 doing freelance work for other bands. 1:31 Throughout that whole process I developed somewhat of a following 1:37 amongst other people in the design community. 1:44 So I worked to get myself any--some kind of attention at some other companies. 1:47 The main thing that got me my first job was I used a website called PureVolume.com, 1:52 and at the time it was like a Myspace music website, 1:57 a network for bands to promote their music and all that. 2:03 So I would find bands on this website that I thought had potential 2:09 to grow as a band, but maybe they were lacking in terms of their web presence. 2:13 So I'd reach out to them and say, "Hey, I'll do a website for you for free." 2:19 And the reason why I was willing to give it up for free was because 2:24 at the time I was in college, and I didn't really need the money. 2:27 I needed things in my portfolio, and that was way more important to me. 2:30 So I actually wrote something about this on my blog at the time. 2:33 This was when blogging was a big deal. 2:36 It was like '04, '05. 2:39 Some referers from that blog, because I had cited how I use PureVolume 2:41 to meet bands, the people who made PureVolume.com found out about that, 2:44 and they reached out to me because they had seen a bunch of my design work. 2:49 They actually offered me a job. 2:52 And they were in Boston, so it was a pretty huge departure. 2:55 I drove all the way over to Boston, and I worked for them for about 4 years 2:59 before moving back to the West Coast, meaning California. 3:02 [Pettit] So where did you go to school? 3:06 [Rosage] I went to school at Western Washington University. 3:08 At that time--I was only there for about a year and a half 3:11 before I ended up moving off to take on this job. 3:13 But I was there to study graphic design, stuff like that. 3:17 They had a course for Web stuff, but it was pretty primitive. 3:23 It was much more focused on, "Well, this is the way of getting your posters online." 3:30 Like, oh, you're just going to be exporting your Photoshop documents 3:35 and then it puts it into Dreamweaver and there you go. >>[Pettit] Right. 3:39 [Rosage] Which is not really a practical way of doing these things at scale. 3:42 [Pettit] So what did you do over at PureVolume? 3:48 [Rosage] At PureVolume, for the first few years, 3:50 my primary responsibilities were--we did a lot of partnerships 3:54 with the record labels that did very custom campaigns on PureVolume. 3:57 So they were doing more one-off pages where, for me, it was really fun 4:03 because I kind of got into design through wanting to make cool graphics and stuff like that. 4:09 I was much more visually focused. 4:14 So getting to work with all these different bands-- 4:17 a lot of bands that I was already a fan of long before I even got this job-- 4:19 it was an honor to be able to work with all the cool stuff that bands 4:23 that I really respected were using to promote their stuff. 4:26 So I would use a lot of these assets and make these pages 4:31 to help them promote their new album or new singles or whatever it might have been. 4:33 But then over the course of time with that job, 4:37 it developed into being more responsible for the actual user interface 4:40 of the website and any kind of new features, designing all those kinds of things. 4:45 So it evolved into being much more product design 4:50 versus doing more advertising design, if that makes any sense, in terms of the difference. 4:54 [Pettit] I was actually going to ask how you made that transition, 5:01 because it sounds like you started out as a graphic designer, but-- 5:03 was it because they were assigning you those things, 5:06 or was it because you really had more of an interest in making product decisions? 5:09 [Rosage] Well, at that time, when I first got into it, I was like 20 years old. 5:14 I didn't really have much perspective on what I really wanted to do. 5:17 All I knew was what I really--I knew what I found to be really fun, 5:21 which was the graphics side of it. 5:26 That's how I got into it, and that was where my attention was. 5:28 And I think that when you work with other people 5:33 that are focused on other aspects of how you actually use visual design 5:36 but have it be more complimentary to a greater purpose, 5:42 which is trying to fulfill or trying to get users through a particular set of objectives 5:46 or whatever. That's kind of a weird abstraction way to say it. 5:52 It gave me this perspective of, how do you apply these things 5:58 in different ways than just artistic? 6:00 Which I think a lot of people think of design as being, 6:03 oh, it's just fun, artistic ways of delivering a message, 6:06 when I think it can be a lot more complex than that. 6:10 And I think once I understood those complexities 6:15 it really changed my interests over time. 6:18 [Pettit] How big was the PureVolume team? 6:21 [Rosage] I think it was about 10 or 11 of us, 6:24 and it grew to be about 25 or so. 6:28 But it kind of went up and down as our goals as a company changed. 6:32 We did a lot of different things. 6:38 [Pettit] So then after that you went to Digg, right? 6:41 [Rosage] Yeah. PureVolume eventually moved to Los Angeles, 6:43 and I was there for about a year doing that. 6:50 After that, I had been at the company for about 4 years 6:53 and had been really heavily intertwined with the entertainment industry, 6:56 music-focused, and I think I was just ready for something new. 7:01 So I moved up to San Francisco, and I got a job at Digg. 7:05 [Pettit] So did you move up to San Francisco without having a job, 7:11 or did you just move here just to try and get a job, or--? 7:14 [Rosage] Actually, I did move up to San Francisco saying that I would be 7:17 working remote, and I definitely took that seriously. 7:23 But ultimately, I did know that I was moving up here where I had a lot more opportunities. 7:28 I mean, that was the greater purpose, I think. 7:32 I didn't really like L.A.; it didn't really fit with me, culture-wise. 7:36 San Francisco was better for that, and 7:41 obviously affords a lot more opportunities in the tech industry 7:43 and for someone with my skill set. 7:46 [Pettit] Sure. So how did you first connect with your job with Digg? 7:49 [Rosage] One of the guys I worked with at PureVolume 7:53 was a guy named Ryan Simms. 7:55 He's a fantastic designer. He's a designer at Rdio. 7:58 He is now. At the time we had worked there, he knew Daniel Burka, 8:01 who was the creative director at Digg. 8:06 He knew him because they had been on a panel together 8:09 at South by Southwest, and so I reached out to him 8:11 because we had worked together for a few years, and I was like, 8:15 "Hey, I'm interested in this job. Do you think you can put a word in for me?" 8:17 And he did, and I got a call back from Daniel like the next day. 8:22 So it was very, very quick and very nice. 8:26 [Pettit] Now, when was that? Was that when Digg was really new, 8:35 or was it a big, popular thing at the time? 8:37 [Rosage] No. This was 2008. >>[Pettit] Oh, okay. 8:40 [Rosage] Or--yeah. It was right before 2009. 8:43 [Pettit] So this was almost at its height? 8:46 [Rosage] Sort of, yeah. Digg's height was probably more around 2007. 8:49 The company--I think once the company grew, at Digg, over about 40 8:53 is about when things--when the focus got a little bit different at Digg. 8:59 When I started working there, it was about 80 people, 9:06 and there had been a lot of cultural shifts, 9:10 and at the time--well, what's funny is that the entire time that I'd been interviewing 9:13 with people at Digg, Daniel was one of the main reasons why I wanted to work there. 9:18 And when I just moved to San Francisco-- 9:24 because we actually interviewed when I was still in L.A. 9:27 Or started interviewing when I was in L.A. 9:29 So when I moved to San Francisco, I wanted to reconnect with him. 9:31 I was like, "Hey, I'm in town. I'm ready to start working 9:33 if you guys are still looking to hire for this position." 9:36 And he said to me, "Oh, you should come out. 9:39 We should go get beers." And so we went out and got beers. 9:42 He told me that night that he was leaving Digg. 9:44 And I was like, "Oh, no. That kind of changes my motivations." 9:49 Ultimately, I still decided Digg was an interesting product 9:54 that I wanted to have the opportunity to work on, 9:56 but it did make it a little bit different. 9:58 In looking back, it was definitely indicative of a very big cultural change 10:02 at Digg as a company, just what the relationships were 10:06 amongst all the people who worked there, especially the people 10:11 who had been working there for years prior. 10:14 [Pettit] Right. What were some of the specific things 10:16 that you got the opportunity to work on? 10:19 [Rosage] There was one main creative director who had filled 10:21 Daniel Burka's position, and that was Jeffrey Kalmikoff, 10:23 who had come from Threadless, 10:27 which is a really interesting T-shirt selling site, 10:30 and it's more that just eCommerce. 10:35 It had definitely more of a social networking or social aspect to it. 10:37 So he was somebody I was really excited to work with. 10:42 Basically, I never really worked with a design team so much. 10:44 So that was the biggest thing that was a new experience for me. 10:47 I wouldn't be surprised if just about any designer who's been first put in that position 10:50 struggles a little bit, because if you're used to working on your own, 10:55 you can make all your own decisions. Having to make compromises 10:58 and all these kinds of things can be a little bit of an adjustment. 11:02 Not to say that they didn't ever have to make compromises like that at PureVolume, 11:05 it was just a little bit different because it was much more mechanized, 11:09 because you're this big company with tons of people involved in it. 11:12 Especially the product itself. 11:17 So definitely it was a little bit of an eye-opening, 11:19 getting used to designing a process even outside of just your design process. 11:21 It was more like a collaborative process. 11:27 [Pettit] Right. So how did that collaboration work? 11:30 Were you just given assignments top down, or did you work with 1 or 2 other designers? 11:33 [Rosage] Jeffrey, who was the manager there, he was very good, I think, 11:43 at trying to put together a plan. 11:49 A little bit frustrating, at times, because a lot of us had different-- 11:55 pretty conflicting ideas as to what vision we had for it. 11:59 And at this time, there wasn't really that product visionary. 12:04 Like, a lot of people think Kevin Rose was the product visionary. 12:07 He definitely was at very specific times in Digg's history, 12:10 but at the time that I came in there, he was very little involved. 12:13 [Pettit] Uh-hunh (affirmative). >>[Rosage] And so there wasn't really that 12:18 one go-to person that everybody at the company could rally behind 12:22 and say that we trust his decision. 12:26 So at that time, the design team was making that decision. 12:28 But because we disagreed so much, there was a lot of ambiguity 12:34 as to what the direction was really going to be. 12:38 And so a lot of that kind of got pushed on Jeffrey, who was the creative director. 12:41 So I think a lot of people kind of looked to him in a negative way 12:46 because they felt like he was the one making the ultimate calls. 12:50 [Pettit] How do you work through those situations, where it takes a long time 12:54 to reach consensus on something where there's a decision that needs to be made 12:58 and just kind of feel like you're talking about it forever? 13:03 What do you push towards? >>[Rosage] I think probably the best way 13:07 to pare down disagreements is to try to take whatever decision you're trying to make 13:09 and break it down to the most fundamental level, 13:15 where you're actually talking about real, objective goals, 13:17 because if you have that one objective goal, 13:21 then any opinion somebody might have, 13:23 you have to put up against that and you have to say, 13:25 "Well, does that fit this objective goal?" 13:27 Because if you say, "Oh, well, I think the button should be green 13:30 instead of purple," or something like that, 13:33 well, you have to then ask the question, "Does that affect the objective goal?" 13:36 I mean, sometimes you won't have an answer, and so you'll just have to 13:40 make a decision in that case, but in a lot of instances, 13:44 people will have strong opinions about how something should be laid out or whatever. 13:47 And sometimes those can lose sight of that objective goal, 13:53 which might be, we want to get somebody to submit a story to Digg, 13:56 and a lot of people are like, "Wouldn't it be cool if the thing flew up 13:59 and spun around in a 360 and unicorns came flying through?" 14:02 Yeah, it'd be cool, but could that get in the way of the objective goal, 14:07 which is to get people to submit stories to Digg? 14:10 I think that's, ultimately, the best process to at least try to pare down 14:15 some of the disagreements people might have. 14:20 [Pettit] Do you think that's your method for making design decisions? 14:22 Just reducing the friction as much as possible and getting to those goals? 14:27 How do you model that in your mind? 14:32 [Rosage] It's hard to say in one general way. 14:35 I think that if you could pose a problem to me, and then I could say that-- 14:39 I could probably dissect that more into saying, 14:44 "Okay, this is what we want to do. Most importantly, 14:46 why do we want to do that? What greater objective does that connect to?" 14:49 I mean, you can extrapolate these things until you get into infinity. 14:56 [Pettit] Sure. >>[Rosage] But you've got to stay close to what you're really 14:59 arguing about, this one particular feature or whatever it might be. 15:04 So, like I said, it's hard to really give one general answer. 15:10 [Pettit] Do you think about the features individually, 15:16 or do you try to contextualize them and always keep the big picture in mind? 15:19 [Rosage] I think always the big picture in mind. 15:24 But sometimes that can also have negative byproducts. 15:26 Sometimes if you only think big picture, 15:29 it can dilute your ability to come up with interesting ways to solve 15:34 the little details, because ultimately, the little details do make up the big picture. 15:40 You don't want to think big picture so much to the point 15:46 to which you create mediocrity. Mediocrity. I think I said that right. I don't know. 15:49 [Pettit] Mediocrity. >>[Rosage] Yeah. 15:54 [Pettit] So you're at Digg for a while, and then, eventually, you went to Treehouse, 15:57 which is where you're at now. >>[Rosage] Yeah. That was awesome. 16:02 I definitely would say one of the most valuable things I took away 16:06 from my experience at Digg was that I met some incredible people 16:09 that are very well-connected with so many great opportunities in this whole area, 16:14 or even--not even just San Francisco, because obviously, Treehouse 16:18 is not a San Francisco-based company, but Kevin from Digg, 16:22 who I work with quite a bit, he was an advisor at Treehouse, 16:27 and he knew Ryan Carson pretty well. 16:33 So it was actually very, very lucky, 16:37 because I was in the middle of trying to find the next thing, 16:39 and so I wrote Kevin an email saying, "Hey, do you have any ideas 16:43 what companies I might want to be looking at doing any interesting things?" 16:50 And Kevin called me on the phone like 20 minutes later, 16:54 which is completely unheard of for someone like Kevin, 16:59 because I'm sure he gets flooded with email-- >>[Pettit] Right. 17:02 [Rosage]--and prioritizing all the things or whatever. 17:05 So I got this phone call from him, and I'm kind of shocked that he called me. 17:08 He's like, "Yeah, Ryan's in town. You should have lunch with him tomorrow." 17:14 And then like an hour later he emails me and he's like, 17:18 "Oh, I didn't even get this email. I just called you because Ryan 17:23 was looking for a designer." And he hit me up. 17:26 So it worked out really well. 17:29 Ryan and I had lunch the next day. He was in town because he was finalizing 17:32 something with some funding or whatever. >>[Pettit] Yeah. 17:36 [Rosage] And I think it was just a matter of weeks later, 17:40 we did some kind of projects for the interview process, 17:42 and then, eventually, I was in the door. 17:46 [Pettit] Wow. That's really serendipitous. I didn't know the full details of that story. 17:50 It's pretty cool. >>[Rosage] Yeah. It worked out pretty well that way. 17:53 [Pettit] Huh. Well, that's cool. So you went on to Treehouse, 17:56 and at Treehouse, we have all of these gamification features. 18:00 Do you feel like that your experience at Digg was valuable 18:05 in putting together some of those features, badges, and things like that? 18:11 [Rosage] Yeah. I guess so. 18:16 I think that a lot of times, if I'm going from one product to the next, 18:19 I don't really like to think too comparatively about, 18:25 oh, this product has badges, and this product has badges, 18:28 so I can somehow match those. 18:31 [Pettit] Right. >>[Rosage] I think that there's bigger concepts 18:33 that you can extrapolate from very different products. 18:37 Let's say one that doesn't have badges at all or doesn't have any kind 18:41 of gamification things, but you can find some kind of overlap. 18:44 So I don't necessarily look to where there's the most obvious overlap 18:47 to find ideas or methodologies that work for something like Treehouse. 18:51 I think that the gamification stuff on Digg had its own mechanisms 18:56 that were very unique to its application. >>[Pettit] Right. 19:02 [Rosage] And Treehouse has quite different ones. I think the motivations 19:06 are very different between the 2 products, and I think that's probably 19:08 where the fundamental difference is. 19:10 Here's one of the big differences. 19:14 If you think about Treehouse, there could be one user on Treehouse, 19:16 and that one user would get the same amount of value to them as an individual 19:19 as if there were a million people using Treehouse, 19:26 whereas a lot of other products like Digg or a lot of these social networking sites, 19:30 they only operate under the constraints of the network effect. 19:34 [Pettit] Critical mass? [Rosage] Yeah. Critical mass. 19:38 So I think that's what makes these things very different. 19:41 So when you say, "Oh, well, Digg had a Digg button, 19:46 and that's kind of like gamification if you want to game the system to get their stories 19:49 promoted and whatever. 19:54 Those constraints of the fact that it's like a network effect versus like-- 19:57 and that's your motivation, is you want to game that system to do that, 20:01 versus you want to game yourself, in a way. 20:05 You're trying to learn things. 20:08 Your motivations are very different, so I think that how you approach 20:11 those problems is very different too. 20:13 [Pettit] When you're designing user interfaces-- 20:16 I often think about problems in terms of design patterns. 20:21 And that kind of helps me chunk things out. 20:25 Do you think about them in terms of design patterns, 20:27 or do you think about what the user is trying to accomplish? 20:30 Because when I think about stuff, I think, okay, 20:34 the user wants to pick 2 things or 1 thing off a list of 1,000 things. 20:36 Okay, I could maybe use Autocomplete to do that. >>[Rosage] Uh-hunh (affirmative). 20:42 [Pettit] Is that kind of how you model things, or do you look to design patterns a lot? 20:45 [Rosage] I think it's a little bit of both. 20:50 For example, for your example, 20:53 Autocomplete is a way to pare down thousands of entries or choices. 20:56 But you also have to ask the question, 21:03 does the user explicitly know what they're looking for? 21:07 Because Autocomplete really only works if they're explicitly thinking like, typing. 21:10 [Pettit] Right. >>[Rosage] You know, it's kind of like that search versus browse idea. 21:14 You don't know what you want; you might want to scan down the list a little bit 21:17 to see what kind of choices you have. 21:20 And then maybe that sparks an idea of what you want to type. 21:23 But ultimately, you might want to get a little bit of a hint. 21:26 So that's kind of where you might have to think about 21:29 what is the user thinking, and what do they want to do, 21:31 versus well, patterns will ultimately take care of it. 21:34 They don't necessarily work that way in every case. 21:38 [Pettit] So what are some of the biggest challenges 21:41 that you've come across when designing Treehouse? 21:43 [Rosage] I think that one of the big things is that there are 21:47 a lot of different ways to learn that work for different people in different ways. 21:49 Like, I think about how we made this change in direction 21:55 towards project-based content versus learning disciplines. 22:00 It's kind of like--the way I've described it to other people was, 22:05 it's kind of like the difference between leaning--the old way would be 22:07 if you just dropped a Spanish dictionary on someone's lap and say, 22:11 "Here. Learn Spanish." Just learn all the words, and you'll just put them together 22:14 in a way that makes sense. >>[Pettit] Encyclopedic. Right. 22:18 [Rosage] Right. Versus someone saying, "Well, let's go somewhere 22:21 where everybody's speaking Spanish and maybe you'll be able to pick it up 22:23 because you're learning it in context and in practice." 22:27 And I think that one of the big challenges was 22:30 coming to these realizations along the way. 22:34 It's like, well, we thought this way for so long 22:38 because it just seemed like the obvious way. 22:40 Like, if you want to learn CSS, we'll just teach you the syntax and you'll have it nailed. 22:42 But that's not really the way that you learn these things. 22:46 And so I think those big challenges were making sense of 22:50 where there was this ultimate friction happening. 22:55 [Pettit] Well, to wrap things up, 22:59 I want to ask you what advice would you give to designers 23:01 that are maybe just starting out? 23:05 Or maybe a better question is, what advice do you wish you could have given yourself? 23:07 [Rosage] Well, before you said the thing about giving yourself-- 23:12 well, the one thing I would say is, which is the thing that I did do 23:14 when I was in college, if you're in a position where you can afford to do things 23:17 for free, especially at a time that you're getting started out-- 23:24 when you're getting started out, the most important thing you can have 23:27 to actually further yourself is to just keep working. 23:29 I know it's kind of a chicken and the egg kind of situation. 23:33 It's like, well, how do I get work if I don't have any experience? 23:36 Well, you need to make some compromise there, in that case. 23:38 Or, you don't have to, but in my case, I chose to make the sacrifice 23:42 of making money, because it was more important to me at that time 23:47 when getting started, to have work to then fuel the next project. 23:50 [Pettit] You have to make your own experience. >>[Rosage] Right, exactly. 23:54 So if you're in a position where you can do things pro bono 23:56 or contribute in some way that can get you work without necessarily 24:00 having to have to have previous work. 24:05 I would recommend doing that, 24:07 because, ultimately, the best way that you're ever going to 24:10 improve in your craft is to keep doing it. 24:15 You can't just listen to what everybody else is saying around you. 24:17 You actually have to put it into practice and learn it. 24:20 Learn by doing, and ultimately, I think that's why 24:23 doing project-focused leaning is ultimately going to be the most effective way 24:28 to imprint these principles in your mind. 24:34 [Pettit] Cool. Well, thanks so much for taking the time, man. 24:38 [Rosage] All right. Thank you. >>[Pettit] I appreciate it. 24:40 [? Soft music ?] 24:41 [Treehouse Friends] 24:43
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