Developer Tea

Live @SquaresConference Interview w/ @KimBost: Part 2

Episode Summary

In today's episode, I had a chance to speak with Kim Bost, product designer at Dropbox! Today's episode is sponsored by FreshBooks! Get paid faster, and get control of your business cash flow. Head over to today to get started with a free month. Thanks again to FreshBooks!

Episode Notes

In today's episode, I had a chance to speak with Kim Bost, product designer at Dropbox!

Mentioned on today's show:

Disclaimer: Design Details, a show on the Spec Network, is supported by Dropbox, but Developer Tea (including this specific episode) is not.

Today's episode is sponsored by FreshBooks! Get paid faster, and get control of your business cash flow. Head over to today to get started with a free month. Don't forget to enter “Developer Tea” in the “how Did you Hear About Us?” Section when you sign up. Thanks again to FreshBooks for sponsoring the show!

Episode Transcription

Hey everyone and welcome to Developer Tea. My name is Jonathan Cutrell and in today's episode I continue my discussion with Kim Bost. In today's episode we will be talking about how Kim ended up at Dropbox. If you missed out on the first episode, the first part of the interview, which is a live interview at Squares Conference, go and check it out at Thank you to today's sponsor, FreshBooks. FreshBooks is the ridiculously easy to use online accounting software designed to help creative entrepreneurs get organized, save time, and get paid faster. We will talk more about what FreshBooks has to offer to Developer Tea listeners later on in today's episode. But first, I want to jump straight into this conversation with Kim. So you're at Etsy and now you're at Dropbox. I stopped in the hall of this story. This is a really interesting, it's like a scenic tour, right? We're unpacking where you've landed as we go along. When I gave my talk yesterday and I went through the same background, a woman came up to me afterwards and she said you basically gave a how to as to how to find another job. That's not intentional. We're trying to find the best job for you. Yeah, I have gotten better at that. Sure, yeah. We ended off at Etsy and what happened next? Yeah, so I was at Etsy for about three years and then I was sort of itching to work somewhere smaller where I could take all of the things that I learned at Etsy and basically to that date and hopefully build a design culture from the ground up. And also I was really interested in building a product from the ground up. And so you can probably guess that I went to a startup because that's what you do. Yeah, all that sounds like a startup. Right. And I joined this company called Cover, which is a restaurant payments product. And essentially you can use cover, it's an app available for iOS and Android. You can use cover to seamlessly pay a restaurant. You check into the app on your phone, you would tell the waiter or waitress that you're paying with cover and then you can leave and you're ready. You don't have to wait for the check. It's the most painful part of a meal is when you want to leave and you can't. Yes and no. Maybe the waiting to get into the restaurant may be slightly more painful. So I did a lot of user research around this. And part of why spoiler covered ended up not being super successful. I do think that seamless payments at restaurants, like someone's going to do this. Could be a good idea. Yeah. But it turns out that paying with a credit card is actually there isn't a lot of friction there. Right. And it's something that you're used to. And the thing that was challenging for us is like if anything went wrong during that experience, then it totally like devalued. Yeah, because you know the credit card is probably going to work. Right. Like it's supposed to be completely magical, right? Like you're supposed to be able to walk out of the restaurants. But because it was so new, you didn't have full coverage. Right. No pun intended, but you didn't have full coverage of the app at every restaurant, for example. Right. Yeah, that's true. But then also the bigger pain point was there's a lot of turnover in restaurants. So we would have to frequently retrain the retrain staff. And so if a staff member wasn't particularly familiar with cover, you would tell them you're paying with cover and they'd be like, well, what's that? Do we even take it? Yeah. Exactly. Or like the worst case scenario would be if they forgot you were paying with cover and then you started to leave. And they'll run after you. Yeah, that was more rare. Okay. So it wasn't a perfect system. Sure. But yeah, it turns out what people would really like make or breaks a dining experience from the research that I did. You would think it would be the food. Right. Like how do really great food? But it turns out that it's from what I heard is it's really about service. Yeah. Like service good service will make a meal memorable. Yeah. Or like go with a good or a bad way. Sure. Every one star app review or a yell preview that I've read is always about the service. Right. Two times. Are they really that upset about the food? Yeah. Yeah. Exactly. Yeah. So I was that cover for about a year. And I worked with a really great team there. We were small and I was working with a product manager Frank Harris who I actually worked really closely with at Etsy. He was the product director there. I was the design director recover. And we brought a lot of the same sort of principles that we had at Etsy over to cover. So product and design and engineering and at this point, we'd even brought marketing into the fold like working really tightly together, collaborating very closely. And some of the best teams that I've been on have like kind of become like family. And when you're really in the zone and you're turning out good stuff, you're like it's like a shared stream of consciousness. And we definitely had that. But we ended up getting acquired by a company based out of the UK who essentially had the same product that we did. And we were their entry point into the US market. Okay. Yeah. Yeah. They like there were a lot of cultural differences. And it wasn't really a great fit for me. These guys had a background in finance. And they were like former ex-investment or ex-investment makers from Goldman and Sachs. So they kind of ran a different. Just different culture. Yeah. Different culture than what I was used to. So I find myself looking for something new. And that's kind of how I ended up with Dropbox. I actually connected with Martin Pedrick. He's the New York lead a few months before I was ready to make the move. And I don't know. I think that's funny. I always get coffee with people no matter what. Right before you work with them. Yeah. Well, no, just to like connect with them. Even if I'm not particularly looking to work somewhere. Or on the flip side, if I'm hiring and someone isn't ready to make a move, I still like to connect with them because you never know when that's going to play out. It's all about timing. And it's all about like, is this the right fit for you? Yeah. So Martin and I had actually connected really early on and talked about Dropbox. And obviously, it was very, very excited about it because Dropbox is a product that I use every day. And it's become invaluable to my workflow. And I was also really excited about the kinds of problems that I would be solving as a designer. There were new problems for me. I've worked on cross-platform products, but I had never worked on client products, on custom products. So that's really interesting. And then also, there's just a ton of complexity to our user experience. So a lot of problems to solve. Yeah. There's a lot of problems to solve. But also, we have so many different kinds of people using our products. Not everyone's a developer. Right. Not everyone is a designer. We're a designer. Not everyone. Not everyone is an academia. Or we have lots of filmmakers. We have lots of people in business. We have writers. Like, basically, you name it. But I want to, one of my, so I don't mean it around, but just to expand on this idea that the people using Dropbox can be very wide range of people. One of the first things that I thought of when I got Dropbox long, long time ago was my parents. Oh, really? You know, this is a great way to share files and pictures and all of that stuff with my parents because we didn't really have a solution other than that. We were using iCloud or anything like that for that stuff. Instead, I said, look, you can just install this thing and put it in this folder. And it'll just shoot right over them. And in fact, to this day, every single episode of Developer Tea, because we have, you know, I live in Tennessee and then Sarah and the rest of the respect team are out in California. Yeah. The first place that it goes is directly in Dropbox. Every single episode we save in a Dropbox. That's great. The variety of uses of this particular, of this kind of product is very wide. Yeah, yeah, absolutely. And we're, I mean, that's so that those are the kinds of relationships that we're thinking a lot about. We're thinking about collaborative relationships. So Dropbox is definitely a place for storage and sharing, but now, right, exactly. For example, right, right, exactly. And so we're looking at ways to add value and make those relationships stronger and more productive and magical. I think that's the word and the delight that you mentioned in your talk, which we'll get into in a second. But the magical feeling of Dropbox, that was the first drawing factor, I think, for anyone that I know, honestly. But this, it was one of the very first native applications that was persistently connected that I installed on my computer other than a browser. Right. Right. And it felt very, very close to the metal for me, right? Which is what I loved. That's what I love. That's what phrase. It just feels so like it's just made it like a native sharing thing. Yeah. It was so different from like the media uploading type stuff that I'd used in the past that felt very transitful. Like I could let it go and never touch it again and forget about it. Exactly. The Dropbox is so integrated and to what I did every single day. Yeah. It's a very interesting difference there that did feel magical. Right. Right. Exactly. Like, it's always very different. And I want to clarify by the way, Dropbox is not sponsoring this episode of developer D. Right. They do sponsor design details, but not this episode. I just really love the products. It's fine for me. You're not being paid to say this. Not at all. No, no, I'm just sitting out here talking with him. And neither of mine, but technically I am. Yeah. Yeah. Yeah. So in your talk though, you discuss this concept of delight. You got this box from Dropbox. Right. Right. So physical box, right? It's physical box. And so backing up from the box for just a second, when I was thinking about what was next for me between cover and Dropbox, I was thinking about three things. So I was thinking about people, process and products. And in that order, right? Yeah. Obviously, people are really important to optimize for because like I said, the best product teams that I've been on, they become like family. And if you're working well together, you start like kind of sharing the stream of consciousness. And so it's really important that you can find people that you can work very closely with. And so like, can you collaborate with them? Is an obvious question, but also can you disagree with them? Is a really important question to you? Because by nature of what we do, there are a lot of opinions. And so you so you've got to figure out like how to work it out and come out on the other side in this constructive way. And then I think about process because obviously a validation driven design process is really important to me. And that makes me sound like a robot. I care about the emotional side of things too, but your process is what leads to your outcomes. And so product is kind of last. And some folks are surprised to hear that. And what I say is like, I'm not, you know, I'm not going to work somewhere where I don't 100% believe in the product. But I think if you don't have the first two things, if you don't have good people and you don't have a solid process, then you're probably not going to build a good product. Or like maybe you are building a good product, but the rest of your life sucks. So those were the three things that I was kind of optimizing for. And that's what kind of let me to drop box. And so yeah, they gave me when I, after I interviewed and they made an offer to me, they sent me this like pink gift box. So it was like a like pink gift box kind of like the size of like a shoe box or something like that. And they had done all of these like hand drawn illustrations on the box of of people that I had met on my interview loop. And it was like drop boxes kind of known for their illustrations and their human, their human side of the brand, especially when it's applied to such a technical product. Right. And these illustrations were done in that style. And it was, it was so thoughtful. Yeah. It was so, it's like one of the nicest things someone has ever done to me or ever done for me. Yeah. And I didn't realize it at the time, but it was like also highly conceptual because what was inside of the box was like this cupcake kit. It was the ingredients and the tools for making a single cupcake. Oh, wow. Yeah. Super, super cute. Yeah. And very specific, very specific one cupcake. And I was just like, this is really nice. I mean, I like cupcakes and I like baking. I was like, maybe they did this because I like baking. And I know like it just took it to the next level. So I took the offer and a couple of weeks later, I was onboarding at Dropbox NSF. And they're, you know, they're talking about company values. And we have a series of values. And but one that stands out for me is one of our values is cupcake. And so at that point, I realized, oh, that's why they sent me a cupcake because we hadn't talked about it before. Sure. Yeah. And cupcake is kind of the silly value, right? And that's the point. Like when you say cupcake, you smile. Yeah. And the value of cupcake is about like adding delight into everything that you do. And so that's both in the culture. And I think that also like, obviously, shines in the product as well because we take something that could feel really complicated, pretty scary and make it super easy to use and not only easy to use, but also like delightful. Yeah. And that comes out in, you know, our illustrations and our user experience. It comes out a lot in our copywriting. Yeah. Oh, I mean, I remember the first time I got an email from Dropbox has said, Hey, you just got an extra gigabyte for no reason at all. Just the best email to get. Yeah. That was great. And that's delightful for many reasons. Not just because it's like, it's fun, but also because it's unexpected value that you just added to my life, right? Yeah. And that's I can see that running through the theme through the through the company. It's really interesting. Yeah, totally. So I want to jump back to something you said with this with this people process and product. To me, I've kind of taken that and distilled it down to what I believe is is kind of like a mantra for someone who who's looking for a job. Maybe you're listening to this podcast right now. Yeah. And you're considering what your next move will be in your career. When you're looking at your job decision, I recommend that you take this and this advice from Kim to look at these three things really specifically because in my opinion, you should be working with people that you can build anything with. Yeah. And you're going to have to like if you're working on like in any work relationship, even if you're working at the most awesome company, there are going to be like highs and lows and projects that drag on and projects that have to go really fast. Yeah. And you may change into an entirely different sector, right? It's possible depending on your product or depending on your audience, maybe you're depending on the market or a million other factors, honestly, you could be building something totally different next month from what you're building today. Yeah. This is especially true by the way for agency work. If you're working in an agency where you're shifting to one client from one client to the next, it is possible that you'll you'll be building a product in the future, for example. Sure. So if you focus first on that people aspect, then the product and the process stuff is going to change over time. You're going to refine your process. For example, you may experiment with your process. Your process may be different based on the people that you work with and your product is certainly going to change. We aren't going to be building Dropbox the same way we build Dropbox today in five years from now. It's going to be a totally different thing. But it's possible that you could be working with those people. Right. Yeah. The people are kind of, you know, that's the foundation that allows you to transcend some of that change. And I think that's a really interesting point because especially the kinds of like cultures that we're working in, like, you know, a small, a small studio or agency culture or like a tech culture that's relatively very young. There are a lot of changes that happen there and there are a lot of evolutions. And I actually think that that's a sign of a healthy culture. A lot of people, especially in tech, there's like a tendency to kind of like shift the organization around, right? Especially like to reflect your priorities because when you have a young product, a relatively young product, you're always like working on your approach to that product and like you're crafting like, well, what is this going to be? Like this is our strength. Like how do we maximize on that and what's next for us? And so you have to organize your people around that. And having, you know, having is again, it's like family. It's like any other relationship having a good foundation there is really important to having people who can be reorganized. Right. Right. Right. And be flexible. So I think when I was younger and like earlier in my career, change really freaked me out. Like it was just it was it was hard to move on to, yeah, it felt that way. Like you would just, maybe you felt like things were going well and then suddenly you were like on a different team or you were just, it's unsettling. And now I've really embraced it and I'm expected. And I think I've just learned how to become more flexible. And I think that's that's actually a good thing. Yeah. So that's like I always like tell younger designers that it's okay when those things happen because it's when the team changes when something shifts. Yeah. And you or you started a new project or you know, just like kind of your context changes. Like that's it's the circle of life. Let's talk about today's sponsor, FreshBooks. FreshBooks is the ridiculously easy to use online accounting software designed to help creative entrepreneurs get organized, save time and get paid faster. FreshBooks has invoicing using FreshBooks to create and send an invoice literally takes about 30 seconds. They have online payments. Your clients can pay you online, which often means you end up getting paid a lot faster than if they had to send you a check in the mail. They have automatic reminders for your clients so that you don't have to send out the awkward email reminding them that they're late on their payment. They also have an expense tracker for you. You can take a picture of your receipts using FreshBooks mobile app and it will categorize them for you to take care of later. FreshBooks also has time tracking, which will help you understand what you did and when you did it as well as cash flow tracking. All the little details about your cash flow are kept in one place. So FreshBooks knows exactly what invoices you sent. When you sent them, who's paid you and perhaps most importantly, who owes you what? To claim your free month, Developer Tealisteners get a free month of FreshBooks. To claim your free month of FreshBooks, go to slash Developer Tea and make sure you enter Developer Tea and the how did you hear about us section when you sign up. That's slash Developer Tea and of course that link will be in the show notes at Thanks again to FreshBooks for sponsoring Developer Tea. Yeah. Well, and to take it a step further, it's also okay if your idea gets turned down. Yeah, I think that's actually good. In a really extreme example, if you're going to get so turned down that you actually are removed from a team entirely and you go somewhere else, like those kind of things. Well, you'd learn that that's not a fit for you. Exactly. Yeah. It shouldn't tell you that well, all of my ideas from now on are going to be bad, right? No. No. It's not a predictor of what you will do in the future. It is kind of a measurement on what you should do in the future. Right. Exactly. Yeah, I think it's really, I mean, everyone talks about how important it is to fail, but I think it's actually more challenging for a company to recognize failure and celebrate failure. Like we're very good about like celebrating things that we ship or things that go well, but I don't know. You don't really like hear about people saying, you know, well, Susie decided to shut down this project because it wasn't going well and this is a good example of something you should do. And I think that we need more of that. I think that's the responsible thing to do. Right. I don't know. I'm like starting on this this new project at Dropbox and some of the first questions that I'm having with the people that I'm working with are like, you know, is this the right area to go into? And even though we've been working on this for six weeks, if we decide right now that it's not the right area to go into, if we decide that this doesn't feel like a good fit or it doesn't match our priorities, we should be okay with that and celebrate that we recognize that early. Yeah. That's not the case. Even I like I'm not even owning my advice. I'm a little relieved by that. But it's important to talk about. Yeah. Yeah. And important to not bury your head in the sand, right? Like if you recognize that something is going poorly, you may be doing yourself more of a favor by killing it early. Yeah. Absolutely. Which is the whole idea that you're talking about is understanding that something is not going well and shutting it down gives you that freedom to do something different. And to do something that's potentially more meaningful and more valuable. And it's all, I don't know, not to get too hokey on it, but it's all a learning experience. Oh, I totally agree with that. And it takes, I mean, it does take a really mature and well-balanced and grounded person to like see that all the time. I'm not saying that things don't get frustrating. But yeah, I mean, have the emotion of failure, right? It's okay to feel let down. Yeah. But it's also okay and encouraged to look forward rather than getting stuck in that let down location. If you go through that experience of failure and you get the chance to start over, then you don't take the chance to start over, then that's that really and we've you hear these quotes all the time. That is the choice to fail, right? Right. Exactly. The choice to fail. And again, I think it's a cultural thing like celebrating, celebrating that people said no to something. So I have two more questions for you. I'm working to wrap up because they're actually cleaning up around here. We've stayed. I could do this all day. This is fun. Yeah, I do this all day sometimes. So. Dream job. Yeah, it's pretty cool man. No, so the first question that I like to ask every developer that comes on the show and it just so happens here at designers. That's what I'm honored to be a designer at a developer show. This is great. This is like my jam. The first question is if you could give every developer just 30 seconds of advice, what would you tell them? And this is a special one for the designer version. Yeah. If you could give every developer 30 seconds of advice of how to work better with designers, what would you tell them? My gosh. So frequently we're in our different silos in our different spheres. And even though like we might be sitting right beside each other, we're not actively communicating with each other. Right. Yeah. And so as a designer, I try to make sure that that we're talking about design with engineering and with development. Yeah. Even if we're way off from building it, right? Like again, like going back to that process that I hated so much early in my career where I would work on something with my team until I thought that we had it right. And we would give it to engineering and development. Instead, I do the exact opposite now. And like from the very beginning, when we're defining the problem seriously and words, when we're writing down like what the goals are or what the problems are that we're going to solve with a given project, I make sure that everyone on the team is in that room. And so that's engineering, that's product management, that's user research, that can be writers, like whomever it is. Because if the entire team isn't aligned on the goals, if you're all trying, if you all think that it's a little bit different, then you're going to have a lot of like turbulence along the way. Yeah. And not only in the beginning, but also throughout the process, throughout the design process, I am making sure that we're talking about our progress and talking about our approach, our approach of making sure that we're all in the same page. Yeah. So like I don't know what the developer equivalent is of that, but just I think it's really about like communication. Yeah, I was going to say just collaborating early. Yeah. And talking to each other and also like kind of like investing in each other. And demonstrating that you can hear each other, right? Yeah. And sometimes that comes down to like making compromises and a trade-offs, but I don't necessarily, I think that's a good thing. Yeah. Absolutely. Yeah. Yeah. Yeah. Yeah. I totally agree. And that's something that's come up over and over on the show is collaboration is key for designers and developers. Yeah. It's fundamental to a good product. Right. It's actually getting that collaboration going earlier rather than later. And also I think something that's key is not having the work be precious. And so that's not having the design be precious, right? Like from where being able to let something go. Yeah. We're trying to find the right direction. And you find that it's not working either because it's literally not working through user testing or however you're you're validating your design direction. And you're like, well, we got to throw it out and start over or iterate on it. And and the same thing for engineering too, like not having the code be precious. Yeah. And two is certain degree. Like I know, obviously some things are more expensive, some changes are more expensive than others. But but two is certain degree like being open on that end to rework ideas as well. Yeah. At Etsy, the engineers were very good about that. Because we again, we all shared the same process. We were all, they were, they were part of that design conversation. They were a part of like sitting in on user research. They certainly like, you know, got the data on the A.Bs that we were running. And so we all together saw what was agreed in on the changes anyway. Right. Right. Right. Exactly. Yeah. Hopefully there's some advice in there. Yeah. Yeah. Absolutely. And the last question I like to ask developers and this one applies to anyone really. Yeah. Is what do you wish more people would ask you about or talk to you about? Oh, that is interesting. Yeah. At this, well right now, I'm thinking, I think a lot of people probably think about frameworks. Yeah. Yeah. And I'm thinking about that a lot drop box because of my experience at Etsy and to some extent what we did, I cover when I was at Etsy, I didn't directly work on this, but a team wrote a new style guide and it's a living style guide. Right. So like if you make changes to the style guide, then it happens everywhere on production. And so I think a lot about how that tool builds not only a like better relationship to your outcomes and to your designs, but also builds a better relationship culturally between design and engineering. And there's a lot of decisions that go into that in terms of like your theories on how to best write front end. Like it's a really hot topic. Like do you want to use atomic units? Do you want to use components? Sure. And like always like a really hot conversation. But I think, again, like going back to like how Etsy had this culture of design and engineering working so easy and so seamlessly together. And I think a lot about about how to recreate that. And then I also think a lot in general about just how to create like healthy collaborative cultures amongst everyone that's on the team. Sure. Yeah. Yeah. So if you if somebody runs into Kim, those are the things that she would like to talk to you about. Oh my gosh. That sounds like a real fun part of conversation. Well, Kim, thank you so much for being on the show. Yeah. Thanks for having me. It's very nice to meet you. This is an honor. Yeah. It's been very enjoyable. I appreciate your time. Cool. Thanks. And thank you for listening to Developer Tea. And once again, thank you to Kim. Make sure you go and tweet at Kim. Her Twitter handle is Kim Bost. That's K I M B O S T. Go and tweet at Kim and thank her for being on Developer Tea. Thank you so much for listening today. And thank you again to today's sponsor, FreshBooks. Make sure that you are taking care of your accounting in your small business. All that paperwork can add up and cause you to go out of business if you aren't taking care of things. So go and check it out slash Developer Tea. You get a free month and you can start sending invoices in literally about 30 seconds. Thank you again to FreshBooks. And of course, that special link and every other relevant link from today's episode can be found at along with all of the other episodes of Developer Tea. Now if you haven't taken the five or ten seconds that it takes to subscribe to the podcast, make sure you open whatever podcasting app you're using right now. I'll give you a few seconds to do that. While I'm talking, go ahead and open it up and click subscribe. This is the best way to keep up with Developer Tea. So you don't miss out on any future episodes. And this helps Developer Teaclimb in those rankings on iTunes. Another thing that is super helpful is a review in iTunes. Let me know what you think about Developer Tea. 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