Hey, everyone, and welcome to Developer Team. My name is Jonathan Cottrell. And in today's episode, I talk with Kim Bost, a senior product designer at Dropbox. This is a live interview at Squares Conference. So you're going to hear a little bit of chatter in the background, but a fantastic conversation I had with Kim. So I hope you enjoy this episode. Today's episode is sponsored by Hired. If you are a developer, a designer, a data scientist, project manager, and you're looking for a job, I recommend you check out Hired. We'll talk about what Hired has to offer to Developer Team listeners later on in today's episode. But first, I'm going to jump straight into this interview with Kim Bost. I am with Kim Bost here at Squares Conference. It is Friday, the last day of the conference, and we just finished up with the last talk. And Kim is... She's nice enough to sit down with me outside in the lobby, which is why you may hear voices in the background. But Kim, why don't you tell everyone... Well, Kim, by the way, is a senior product designer at Dropbox. Yep. So she knows her stuff is the easy way of putting it. I pretend to know my stuff. Yeah, there you go. Can you tell everyone who's listening kind of where you came from and how you got into design and then ultimately ended up at Dropbox? Do you want the long story or the short story? Your favorite version. My favorite version. I'll add a little color to it. So you asked where I'm from and like, I'm like, well, I'm from West Virginia. There you go. Okay. That's a good place. Yeah. So I grew up in West Virginia and I grew up in a pretty small town called Bluefield. There's about 17,000 people in Bluefield. So it's really small. It's not exactly a hotbed for design. But I... Was always really interested in design from a very young age. Like from the first time that I was actually kind of like introduced to computers in elementary school. I was introduced to this program called Logo. Interesting. I don't know if you've heard of it. I've never heard of it. Was that on an Apple II or something? Yeah. And it was a program where essentially you could type in coordinates and positions and they had this little cursor called a turtle and you could draw things with it. And that was like, I was just enamored with it. I loved it. And I moved from Logo to kind of like desktop publishing and I would use like desktop publishing software. And mind you, like mind you, I'm in elementary school. Sure. So I'm a kid. Yeah. And I would like... Like book layout, right? Is that... Yeah, that kind of stuff. But for me, it was more about like birthday cards. Like I would never let my mom like buy my friends birthday cards for their birthday parties. I always insisted on making my own birthday cards. Because you wanted to put like their favorite animal on there. Yeah. I think at that point it was kind of like more about my vision and less about customizing it for them. Your favorite animal on their birthday card. Yeah. Yeah. And I went from there to a little like later, like in junior high or high school, we got a gateway computer. That was our first computer in the house. And I convinced... With the cows on it and all that? Yeah. Yeah. Exactly. And the preloaded software that slowed it way down. Yeah. Right. It was pretty slow. Yeah. And I convinced the guy who would like come and repair it because it breaks down a lot. Sure. To give me a bootleg copy of the software called... I think it was called... I think it was just called Paint or Splash maybe. Okay. It was called Splash. Yeah. And I remember like having to type in the path to like load the application and all of the... Oh, wow. Yeah. And again, I was a kid. So I remember meeting with him and like taking very explicit notes about how to load this application. And then I went from there to like taking Votek class. Yeah. Yeah. And then I went to college and I went on to get a master's degree in graphic design from MICA in Baltimore. Okay. And then from MICA, I went to the New York Times. And that was kind of like my big break. And to this day, I'm still surprised that I got that job. Like I remember interviewing for that job and standing outside of the building and looking up at the New York Times logo. And I was like, there is no way this is going to happen. But then it happened. Yeah. And you were there. Then it did. And I was there for four years. And I actually had two jobs. So when I first started there, I was the art director for the op-ed section of the page or of the paper. Yeah. And I was working on the physical newspaper. So I was doing layouts and working with the editors to art direct the page. And so I would hire some of the world's best illustrators and artists to art the articles. And it was a really interesting time to work in the newspaper because it was during the 2008 election, which was really crazy. And only the 2016 election is crazier. I didn't think it would get any crazier than that. Talk about today's sponsor, Hired.com for a few minutes. On Hired, software engineers, project managers, data scientists, and designers can get five or more interview requests in a given week. Each of these offers has salary and equity up front. And they have full-time and contract opportunities. Now, you as the user, you can view your interview request and accept or reject before you ever even talk to any company. So there's no awkward conversations. Hired works with over 3,000 companies, ranging in size from startups to large public companies. And the best part for you is that it's totally free. They hide your profile from current employers and anyone else you want. So you have full privacy as well. Now, normally Hired offers a $1,000 thank you bonus. But if you use this service, you can get a free copy of the interview request. And you can get a special link, which you can find in the show notes at spec.fm. That bonus will double to $2,000 just for using that special link. So go and check it out. It's Hired.com slash developer T. And of course, once again, that will be found in the show notes at spec.fm. Let's get back to the interview with Ken Bost. So you could go back now and it would be absolutely crazy, I'm sure. Yeah, particularly in, I mean, news is crazy, but in editorial as well, because you're writing all of these opinion pieces, which is really fun. Which can be way more extreme than the others, right? That's the point, right? You want to have extreme, well thought through opinions sometimes. And that's actually where I got used to shipping every day, because you're shipping the newspaper, obviously. Quite literally every day. Yeah, literally every day. And then also when something particularly newsy would happen, even if we had laid out the paper and had everything set, we were getting ready to send it off to the printer. It's like, you know, the end of the day, 6 p.m., whatever. We'd have to tear it up and do it all over again, because we want, obviously, it's the news. We want to be on topic. And a lot of people probably would get stressed out in that situation, but I loved it. And I still love it. And I don't know, I actually, like, I think I really kind of thrive under pressure. Yeah, so I like working fast. But I did that for two years, and then I ended up on the interactive team. I actually, when I... At the New York Times. At the New York Times, yeah. And I worked on a mix of news design features and editorial features. And at the same time, I was sort of spending my nights and weekends in a design studio in Greenpoint freelancing. It's called the Pencil Factory. Okay. Yeah, it's actually an old pencil factory is where I had my freelance studio. There's one of those, I think, in Atlanta, if I remember correctly. Yeah, I think I remember that correctly. Maybe, yeah. Pencil Factory Lofts or something like that. Yeah, that's funny. There are Pencil Factory Lofts in Greenpoint, Brooklyn. I guess pencils are going kind of out. I don't know. I don't know what the deal is, but... Yeah, it's a cool space. But I actually, at the time, there was like a whole crew in there. So Jessica Hish was a part of that. Oh, wow. Jennifer Daniel was a part of that. And like Josh Cochran, Sam Weber. Great team there. Yeah, yeah. It was really like a special time to be there. And I had like freelance clients. And I was teaching myself to code and write HTML and CSS. And... So you were interested in code relatively... I'm giving a little preview to what we're going to be talking about here shortly. But you were interested in code relatively early in your design career. Yeah, definitely. And that was not the first time that I had coded. Like I coded a little bit in grad school. And actually, when I was an undergrad, and this is like embarrassing to say, but I... I was responsible for web design at a small like design studio that I worked at in Greensboro, North Carolina. Because I was the kid in college who knew about web. And they were like, well, our clients want websites. And you kind of know how to build them. So here you go. That's great. Yeah. Yeah, it was good. But at the time, it was the early 2000s. It was probably like 2000, 2001. And I would build like very basic websites in HTML. Or awful to say, I would build websites. Yeah. Like Flash. Yeah. Yeah, no, it's a part of all of our past. Yeah. So you'd have these like massive files that would take forever to load. And they had all of these like extreme animations. But yeah, I've always been kind of interested in it. But around 2010, 2011, I started to get really serious about it. And it started to influence how I think about the design process. And so I really wanted to work on a team, particularly that worked really collaboratively. with engineering when I was at the times. And I think that a lot has probably changed since I worked there. But we were spending a lot of time like sort of making these pixel perfect PSD mocks, redlining them and then sort of like tossing them over a wall to development. And they would spend six weeks building something and then they would bring it back to me. And you know the story. Yeah. I'd be like, this is not even close. Yeah. Or maybe it's close, but we had to send it back because it's just slightly off. Yeah. And then they would be like, we can't do this. We can't do that. And then I would like send them the CSS properties to fix it. You knew they could do it. Yeah, I knew. But it's just, it was like frustrating for me and I think it was frustrating for them. And it just is, I don't think it's the best use of anyone's time and it's certainly not a good way to work together. We both have more to offer to the problem, problem solving, then that kind of relationship. And so long story short, that's how, that's how I ended up at Etsy. Um, because I think my first meeting or no, the job description for a product designer at Etsy said, if you'd rather walk a hundred miles in the, in the desert, then red line a Photoshop comp, then like you're the designer for us. And you're like, that's me. That's a hundred percent me. I was like, preach it. I am in. That's great. Um, yeah, yeah. And so I joined Etsy and the teams are very collaborative. They're very small. They're like engineering and product and design, uh, essentially like share a brain. Yep. Um, and also all like really important to me, all of the designers, uh, code there, or at least they did at the time when I was there. And, um, Etsy has this, uh, continuous development process. So you're constantly all day long pushing code to the site and designers are welcome to do that too. They drive deployments. And so I just learned a ton while I was there. Yeah. Um, and, and I, I think I kind of took that culture for granted a little bit because I didn't realize. Um, how hard it is actually to have a culture where design and engineering are, uh, are sharing a code base and working so like seamlessly together. Like there's a lot that has to go into that. Like when I first came on board there, the engineers did have to invest in me a little bit. Like they had to teach me how to work really, uh, work with GitHub really well. And also, um, sort of like, you know, I had to improve some of my CSS skills cause they weren't great coming in. I'm going to be honest. They're good now. They're decent now. But when I first joined the team, they weren't that awesome. So there was this investment on their end. And the thing is they didn't blink about it though. They were ready to help you. They were totally bought in. Yeah. And I didn't, at the time I didn't realize how, how exceptional that is. Yeah. That's well, I think, you know, being on a team where there are distinct positions for designers and developers, because not every team is that way, right? No. Yeah. Some teams actually really do totally merge those, those two things. To be the front end person, right? Like front end means both design and development, but being on a team where those two things are distinct, uh, and having tasted what it could be when you're truly collaborating. Yeah. Like they had at that point, right? They, they knew what it felt like to collaborate with designers. I would imagine that that's kind of their minimum, like they would never let you not know those things, right? Like, uh, that investment is such a, such a huge return for both sides of that. That fence. Absolutely. I can only imagine that they were more than happy and ecstatic to say, okay, Hey, yeah, let's sit down and I'll show you everything you want to know about our, you know, our, about, about our, our code base or about our, you know, front end flow or whatever. Yeah. They were very open to it. And I think, I'm not sure where they got that though. You were, you're saying like they would be ecstatic to do that. But I think that maybe, um, engineers first need to taste the value of that or understand that. And the value of that before maybe you're fully bought into it and designers too, right? Like lots of designers are like, why should I learn how to code? Because it takes investment on both sides of the fence there. Yeah. And yeah, it's definitely an investment. It's not, um, it's not something that I learned overnight. It took years of, of working at it. Just like most of my design skills though too. Like my typography skills weren't on point on day one. Yeah. They sucked. They're pretty dope now, but it took a long time to get there. It didn't go, didn't happen right away. Right. Yeah. Sure. I can only imagine. You know, being in a, in a situation where you have that many people working on the same thing, um, it's such a powerful thing to be able to say, okay, we know this works. And when we have new people come in who don't know that it, that it works, we're going to show them by actually like bringing them into the fold and saying, Hey, we know that this is weird and out of your norm. Yeah. But once you get it, you'll really get it. Yeah. And that was a hiring requirement for us at Etsy when we were interviewing designers, the requirement was not. Not necessarily that you were able to write, um, semantically awesome CSS or even, you know, we hired some designers that did not write HTML and CSS at all, but it was more that they were open to learning. It was more that there was that curiosity and that design or that desire to work that way. Yeah. Yeah. Yeah. So when you show them, when you show them a demo of code, they're actually, they actually care about the inner working pieces and parts. Yeah. We would give them a coding exercise. Okay. Yeah. Yeah. So we would, um, I think what we would do is we would have like a basic mock of the design and we would have everything kind of set up for them and we would just ask them to write the HTML and the CSS for it. Sure. And some people, they had an hour to do it and, um, and we were realistic about it. Like we were like, Hey, it's totally fine to Google stuff if you don't know it. Cause that's your real working environment. Like you hit a wall, you're going to look it up. No big deal. Exactly. Yeah. Um, some other places aren't like that. Like I, uh, I did a interview at Google once and I had to like, I was like, I'm going to like whiteboard CSS, like a true engineering interview. Um, I think I did. Okay. Yeah. I've heard some horror stories around, around the whiteboard of, uh, you know, algorithm, you know, trying to write an algorithm on the board and some of the smartest programmers out there who fail those tests. Sure. And, and that kind of makes sense too, because we all know that, um, humans test differently, right. And they perform differently in different situations. That's true. And so. So no matter what kind of tests that you're using, um, you, you, you have to take into consideration, people have different personalities and different performance styles and, you know, a whole like multiple choice versus essay thing. Oh yeah. Yeah. Well, and I notoriously, I tested well, but my sister didn't, for example. Right. And, uh, she's very smart. Yeah. And, and we could have, you know, we competed on many levels, but she just, she just didn't test well. Right. Uh, it is definitely a. It's like one person to the next person. It can be wildly different and have not very much to do with necessarily intelligence. Yeah. You have to get multiple signals. Like also from a design point of view, designers typically have to give a portfolio, uh, review. And especially if you are a more junior designer, your communication skills probably aren't that developed yet. Right. That's part of like becoming a, you know, a senior designer is being really good at, you know, walking through your ideas. And presenting your work and being articulate and all of that stuff. And so. Documenting what you're doing. Yeah. Yeah. And, um, so I think that sometimes that can be really unfair if you're trying to hire a junior or a mid-level designer. Not that you shouldn't do it. You should do it. You should absolutely do it because you do want to see, um, obviously you want to see someone's work and their process and how they think through a problem, but you have to take those factors into consideration as well. Sure. Yeah. That makes total sense. Yeah. That makes total sense. Thank you so much for listening to today's episode of Developer Tea. My interview with Kim Bost. We will continue the interview in the next episode of Developer Tea. We're going to talk about how Kim ended up at Dropbox. So it's a great conversation. I was so happy to talk to her. She was such a kind person. We talked even beyond this recording. We had great conversation while we were there in Dallas or rather in grapevine Texas. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. to talk to her. She was such a kind person. We talked even beyond this recording. We had great conversation while we were there in Dallas, or rather in Grapevine, Texas. And another huge thank you to Squares Conference for having Developer T come out and hang out and watch all of the wonderful speakers there. I really appreciated all of that. So thank you to Squares. And once again, thank you to today's sponsor, Hired. On Hired, you can get five or more interview requests in a single week. So if you're a software developer, or if you're a designer, project manager, data scientist, any of those things, if you're creating things with computers, and you're looking for a job, go and check out Hired. Hired.com slash Developer T. Once again, that link and everything else from today's episode can be found in show notes at spec.fm. Thank you so much for listening. Make sure you subscribe, by the way, in whatever podcasting app you use, so you don't miss out. Any future episodes of Developer T, including the next part of my interview with Kim. Thank you so much for listening. And until next time, enjoy your tea.