Episode 15: Angela Gorden, Dropbox - UX Writing at Dropbox

Kristina: Hello again. Welcome to The Content Strategy podcast. I’m your host, Kristina Halvorson. This podcast is brought to you by ContentStrategy.com and Brain Traffic, a content strategy consultancy. Find out more about Brain Traffic at BrainTraffic.com.

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Hey, thanks for joining us again. I, this week, am super ... Well, first of all, I have a little bit of a cold. I’m sorry if I’m nasally but secondly and much more importantly, I am super excited to welcome Angela Gorden to the podcast today.

Angela is a UX writer for Dropbox. She lives in Berkeley, California. I almost said Colorado, that would have been dumb. Clearly Berkeley is not in Colorado. I have a cold and am a little fuzzy. She designs with words and shapes product content strategy, which we are going to talk about in depth today. Angela, hello.

Angela: Hi Kristina.

Kristina: Welcome to the show.

Angela: It’s really great to be here. Thank you.

Kristina: I’m so happy to have you. Hey, I usually kick off my conversations by asking people to tell me a little bit about their journey to content strategy and in your case journey to UX writing. Can you tell me about that a little bit?

Angela: Yeah. I’ve been a UX writer for the past three or so years. Before that, I spent a long time working in the publishing industry, book publishing, and I really enjoyed doing that work. I was a developmental editor. I worked with content and helped structure books and worked on things like organization and voice and …

Kristina: What kind of publishing were you working with?

Angela: Psychology.

Kristina: Oh psychology.

Angela: Psychology books, a lot of self-help books, some memoirs.

Kristina: Oh cool.

Angela: A lot of books just about people’s psychological issues and stuff.

Kristina: Inner workings.

Angela: Yeah, exactly, which I love to know about, like what makes people tick.

Kristina: For sure.

Angela: I really loved doing that work but after a while I started to get more interested in working on things that were more interactive than physical books, and the company that I worked for was investigating the idea of doing an app and I started working on that project and that led me to learning more about UX design and I eventually went back to school for that.

After a while of just studying UX design stuff and design thinking, I realized that I wanted to be more of a specialist than a generalist. So I learned about content strategy and UX writing more specifically and I was really excited to learn about this field.

Kristina: What school did you go to? What program was it that you were in?

Angela: I went to Stanford. I was in this program called Learning Design and Technology, which is part of the education school at Stanford. When I was there, I took a lot of classes at the design school where they have a lot of workshops and things about design thinking and process stuff. So I was in the ed school but I studied a lot of design thinking.

Kristina: Where did you first hear about UX writing or where you just like, okay, I like this approach but I miss writing. I mean, where did that come from?

Angela: Actually, a friend of mine had gone to the same program and he had become a UX writer and I was talking to him about, like I had a more general job as a UX designer, but I was talking to him about looking for something that was more specialized, and he told me about the field. I actually didn’t even … I was like, what do you do? I had no idea what this role is and he’s the one who introduced me to it.

Kristina: Interestingly that phrase or that title is relatively new. I mean, it’s just been here the last couple of years and the companies that started using it are really sort of on the west coast, out in the California, Seattle area where you work and I find that that title has not caught on very much throughout the rest of the country and I think in a lot of instances in the UK and throughout Europe, “content designer” is actually a little bit more in line with that title but I think there are also differences as well that I’m going to want to talk about in just a little bit.

But tell me, so now you’re a UX writer at Dropbox. Tell me what that means at Dropbox and what you do day to day?

Angela: At Dropbox, UX writers are embedded in product areas. We work … we all work in different parts of the Dropbox product and that means on a day-to-day basis, we collaborate with product managers and engineers and product designers. We work together on these teams to develop different experiments or different projects and stuff for the Dropbox product.

We do have things where we have weekly writing workshops, biweekly writing workshops, where the UX writers all get together and exchange ideas and give each other feedback but on a day-to-day basis, we’re embedded in the product teams.

Kristina: Okay, I’m going to have you pause for a second because I have questions about both of those things. Are you working on one product at a time?

Angela: Yeah, I work on Dropbox Paper but within Dropbox Paper, there’s different teams and I’ve been working on growth, the growth team, and then within growth we have multiple experiments.

Kristina: Experiments you said?

Angela: Yeah.

Kristina: What does that mean?

Angela: It might be like, what would happen if we add a modal when people are signing up for instance, or what shall we say in that modal? Could we tailor the content for specific users coming from different sources?

Basically, playing around with different content and different design patterns and seeing, does that have an effect on what we call activation. Which is like people using core features of Paper and basically like how can we remove the needle on that?

Kristina: How do those meetings take place? I’m trying to … For example, I’ve been at companies where it’s like okay, we’re going to work on this specific feature of this product and it is literally the writer or the content strategist and the product designer and the engineer are all sitting around the computer, whatever, kind of tweaking and suggesting and developing and testing right there over a two-hour period. I mean, what do those meetings look like?

Angela: Well, they kind of depend on the project and generally, like in general we work in sprints. Like we have six-week sprints and we have a kind of an idea of the different strategies or experiments that we want to try out. You kind of have a little bit of an overview, or a preview of what you’re going to be working on the next month and a half.

And those are all scheduled. So as the sprint progresses, we have kickoff meetings and we talk about like what are the strategies? What are the goals of this project? Why are we doing it, that kind of thing. And then I also have one-on-ones with all the product designers where we work on, we talk about what we’re working on, what we might want to try for a project, that kind of thing.

Kristina: Sure, so one of the things that I have found over the years with agile and a real kind of complaint or concern that I’ve had to share, and I know you know this, but agile is a methodology for building product and it was born in the software development community and has since been adopted by a number of different disciplines including ways in which you kind of run your company and how people need to operate throughout all areas of the company, not just within product development but—and that’s a whole different conversation—but one of the things that I have seen over the years is, especially when people are trying to use agile for website development.

But in product too is that a lot of times the product will be sort of shaped and the sprint will be defined and the roles will be defined and that there’s never a writer at the table, that they’re focusing on tools and visual design and flow and buttons and all that stuff but that the writing sort of comes as an afterthought or something that the engineer is trying to crank out or the designer is sort of putting placeholders up.

Tell me about, when you came to Dropbox, was it just like, yup, the writers are the table, at the beginning, or how did that evolve over time for you?

Angela: I do think it is a process of evolution and Dropbox is one of the most inclusive of writers in terms of product planning and stuff of the places that I worked, and I think, and it has gotten better and better over time. I think everyone understands that UX writers really are equal partners in the process.

We’ve kind of set up things, things where UX writers are included as stakeholders on templates or when people set up meetings for a project kickoff and stuff like that. There’s always a spot for a writer to just make sure that people are inviting us as a matter of course.

I also think that planning is a big factor. Looking ahead to the next sprint is a time when I as a UX writer can kind of help set the course or bring up issues that are related to content or storytelling and stuff. Us being more and more involved in sprint planning, has been a thing that we’ve really worked on in the last year or so, and I’m speaking mainly from my experience on Paper, which is the team that I work on. That is kind of a big opportunity I think for writers to sort of like … I try to have kind of a backlog of ideas that are related to writing or opportunities, things that we can build on from previous experiments that were related to content and I try to bring those up in brainstorms and planning sessions.

Kristina: One of the things that I have seen work really well too is that … what will oftentimes kind of blow up projects or designs in the eleventh hour is that all these questions about content and copy come up that nobody’s thought to answer until the very last minute. What are some of the … You’ve got different ideas that you are participating in these planning meetings. What are some of the kinds of questions that you will ask to kind of get people’s brains working to help them realize that you really need to be at the table from the start?

Angela: In the beginning part of a process, I really lean into the part of my job title that’s the UX part. So I really focus on user experience and I ask a lot of questions related to the flow. So what users see before they would encounter this, these screens are part of the experience that we are proposing, what are they seeing next, do we have any related research that can kind of clue us in on user motivations and needs and stuff, do we have customer feedback, do we have analytics? Things that are going to help ground the project in real user needs.

I also ask a lot of questions about how is this related to projects that we have done in the past. Can we learn anything from what we’ve done before and take another approach this time or build on something that seemed to work?

I really focus a lot on those fundamental UX-y kind of questions. I really lean into the … Basically, I’m focusing on that because it really helps me as a writer later on down the line make choices more quickly, decide between different copy directions. And also if I know something of the background of the project, I can reach out to UX writer on another team that may have done something similar.

I think as I’ve grown as a UX writer, doing that part of the process has become more and more … I’ve seen that it’s more and more important that can really help me move more quickly.

Kristina: What advice would you give to somebody who … because that’s all smart content strategy thinking, right? That’s all standing up for user needs when it comes to storytelling or direction or voice and tone or what’s included, what’s not, getting out of people’s ways, so there’s not a ton of extra copy or content, et cetera.

What advice would you give to somebody who is sort of also working with product development teams in the sprint cycles and who is still just kind of getting pulled in when it’s time to fill in the words. What advice would you give to them?

Angela: I think that when you’re in that situation, I do think that a really important question to ask is how are we going to know, how are we going to define success, because even if you don’t have a lot of the more foundational stuff, you kind of have a sense of what the objectives are of the project. If you can get people to articulate that clearly.

I found that sometimes when I do ask questions like that, I found that sometimes there are assumptions being made or people haven’t fully thought it through. It winds up being helpful for your teammate as well as the whole team, if it helps bring clarity.

I also just think that when you’re in that situation, being transparent about your process can also help because if you show … maybe you are asked to fill in some button copy or something and it’s two words and you show that you’ve done like 30 explorations on it. You’ve really gone all out in trying to find just the right way to message something, it sort of helps … over time it helps people understand that maybe we should give her a little bit more time or more context because they see that isn’t just … you’re not pulling these words off the top of your head. You’re being really rigorous and there is a process. I like to be transparent about how … I share the results of what I am proposing but I also share explorations and I think just in the long term that can help change things.

Kristina: That’s really smart to sort of show people behind the curtain that this is not, I do not just sit down and come up with this. Like you said, off the top of my head because I think that is a common thing where people are just like, it’s words. How hard can it be? Everybody just write some words and just go out there.

I think that that … Talk to me a little bit about, you used the word “exploration” and being transparent with, “Look, here’s the 18 different ways that I tried articulating this and this is the one that I recommend.” You also talked about experiments that you defined this and that you’ll put stuff out there and see how people react to it.

Talk to me a little bit more about the process of experimentation. How does Dropbox get that out there? How do they measure it? How do you use the responses to iterate your work? Just talk to me about that a little bit, like just give me an example.

Angela: Exploration, the exploration part of it is something that I’ll do often on my own and then with the product designer and other UX writers. I’ll come up with lots of different versions and I workshop things a lot. I will ask other UX writers to give me their feedback and their ideas and stuff.

I like to also share explorations with product managers as well. I try to do it fairly quickly just because I feel like in my role, I have to kind of move quickly, like I might have three days or something to work on something. Being able to get as many ideas and input as quickly as possible is important and kind of builds a sense of momentum.

With testing, we also have this thing we called Real World Wednesday at Dropbox where we will come up with a basic prototype of an idea. You can also test copy in the prototype or you can test copy outside of just words separately and we bring in users or potential people who haven’t used Paper or a feature in Dropbox, and we ask them to try out a mock or a prototype, and basically it’s like super scrappy user testing and we do that every other week.

That’s really helpful just to get people’s reaction. Many times I am surprised that, oh that is not clear at all. I really need to rework that part of the phrase, or sometimes … maybe I think that a certain phrase is kind of clever or fun and someone else might, some of the people at Real World Wednesday, they might see it as like, “Oh that’s insulting and patronizing.” I’m so glad that I tested it.

Real World Wednesday is a really big part of testing and then we also have UserTesting.com and our researcher does more extensive testing of usually not prototypes but real things that are live in a product and he gathers user feedback from those tests.

Kristina: Yeah, well great.

Angela: Oh I’m sorry. The other side of it is analytics.

Kristina: Sure.

Angela: We do have analytics for like if we do build something out, we have an analytics team that will tell us what people are clicking on or what happens after they engage in one of our experiments.

Kristina: Great. Do you get to see those analytics and respond to them directly? Is this sort of, is there a project lead that’s coming or a team lead that’s saying, “Okay, based on analytics, here’s what we’re going to focus on.” I mean, how do they know or how do you know that what they’re measuring is meaningful?

Angela: We have a product manager who usually works with the analytics person to basically interpret the results and to report back to the rest of the team. I am actually working on increasing my knowledge about analytics and metrics and stuff because it is something that I’m interested in and I think can be very helpful. It’s just not an area that I’m super confident in being able to interpret myself.

Kristina: Yeah, this is actually a skillset that I really recommend for content strategists and writers to sort of become familiar with. I mean, I think the two areas are analytics and then SEO as well and that’s not as important obviously when you’re talking about writing embedded within a product experience but yeah.

Angela: Yeah. I want to just get better at understanding what to measure and like you said what actually is meaningful. Our analytics team, they have office hours and they do some evangelizing about their discipline. I really want to take advantage of that more.

Kristina: Oh, that’s so smart for analytics people to have office hours. That’s so smart. Oh I’m going to start preaching that. That’s great. Hey, explain to me now, where do you … so you sit within Paper, Dropbox Paper, but then you also mentioned that the UX writers get together regularly for workshops or work sharing or whatever, tell me a little bit about that and how that works?

Are there UX writers, are you assigned within Paper? Do you report up to Paper leadership? I mean, tell me where UX writing as a discipline lives within Dropbox?

Angela: It is kind of distributed. We have managers for different product areas of Dropbox, and within Paper for instance, we have three different UX writers and we all have the same manager but we work on different parts of the product and we have our … we have a weekly checkin to talk about projects that we’re working on for Paper just so that we can stay aligned, and then within Dropbox more generally, we also meet up with the other UX writers once a week as well.

Kristina: Once a week? Wow.

Angela: Yeah, well we have once a week for our team meeting and then we also have two workshops separately but we have a lot. Dropbox is very … really, really advocates for feedback and collaboration. I think that’s reflected in like we have these two writing workshops and then we have the one team meeting and then we also have one Paper meeting as well.

Sometimes it does seem like, oh we have a lot of meetings, but the thing is that they’re more like working sessions, where we’re like getting stuff done. It’s not just sitting and listening. They’re more active than a lot of other meetings.

Kristina: Can you give me an example of something that you might work on in one of those meetings?

Angela: As I mentioned, I have a pretty quick turnaround time for a lot of projects, like we have three days or something scheduled to work on something. So I might bring my initial ideas for the project to the group, the big all the UX writers at Dropbox getting together and we have different types of feedback, like you can say, “I’m looking for directional feedback.” “I’m looking for guidance.” “I’m looking for just trying to close this out and finalize it.” “I want to refine it …” There’s different types of feedback. You can ask the group for a specific kind.

I like to workshop things in different stages. I find that the getting direction phase is very helpful for me. It helps me just get things moving with a project that maybe I’m stuck on or I haven’t had enough time to really dive into. So we kind of put our minds together and think about what are some different ways to approach this. People talk about, they might tell me a project that they worked on that’s similar in the past. They might send me a link or something to their writing doc that they worked on.

Basically, it’s a very focused brainstorm session but then other times I might workshop something that I have worked on it a while with product designers. Maybe I’ve already shown it in the design session, which is another place where I get feedback on writing and I’m just trying to refine it. So I’ll already have like, this is what I’m thinking of proposing. Do you think there’s ways that can make it better? Then we just do a lot of wordsmithing.

Kristina: This is really interesting to me that there is that much sort of open sharing and opportunity for feedback because I find that no matter who you are and how thick your skin is, that as a writer sometimes it can be difficult both to take feedback and then also to kind of give feedback in a way that maybe is going to be constructive but not push somebody away.

Do you find that you’ve gotten better at receiving feedback? Do you ever give feedback to people who are giving feedback? Like tell me a little bit about how that works at Dropbox?

Angela: I have, because of my background I think in publishing where I was an editor, that was main job was giving feedback to authors. I have a lot of experience and practice at doing it. It is a little different when I’m receiving it though. I feel like … We didn’t use to have the different types, like asking for different types of feedback, being very specific, like I want this kind, I want to refine this. I am trying to close it. I am exploring ideas. Before we introduced that framework, it could get a little bit dicey where like maybe I’d be trying to close something and then we would start brainstorming in a completely different direction. That can get frustrating, because you’re like but it’s due tomorrow. So I think that that framework is really helpful.

Kristina: So repeat that again, it’s directional, what are the different kinds of feedback?

Angela: Okay, it’s guidance, do you want guidance? Do you want to refine what you’ve already created? Do you want to get alignment? I think the directional and guidance are the same thing. I think those are the … Yeah, guidance, direction, and closer.

And then sometimes people … you’ll just workshop more of a concept or a principle and that is more like alignment. We have an internal style guide for UX writing. We’ll be like I think that we should do this. What do you guys think? Do you think it will work on these different surfaces that you write for? That is more alignment across the company. I think that’s a really big one.

The UX writers are, it’s an amazing team, and people are very open-minded and flexible. I don’t think that people feel that there’s only one right answer to something and that keeping an open mind is a really big part of being able to receive feedback.

Kristina: That takes a certain kind of personality. Like it sounds like there are some personalities that just would not roll at Dropbox.

Angela: Yeah, I do think that being open-minded and soliciting feedback is one of … those are some major parts of succeeding at Dropbox.

Kristina: I actually think that would be a great conference session or blog post, which is how to go and get and then receive and also to give feedback.

Angela: Well, that’s a good idea.

Kristina: I’ll be expecting a first draft from you by the end of next week.

Angela: Okay, I’m going to get on that.

Kristina: Yeah, exactly. My needs, you know what I mean? Tell me about this style guide that you have at Dropbox? We use Dropbox here at Brain Traffic and of course just love it. And one of the parts of it that we love is that it is simple and it’s delightful, and when you do encounter content or copy, it is consistent and it is conversational and it doesn’t get in your way. Who owns the style guide? Who works in the style guide? Who is responsible for sort of making sure that things are consistent and on brand? How does that work?

Angela: Yeah, it is definitely a team effort, or effort of multiple teams. We have a content style guide that … one of the UX writing managers sort of coordinates it and manages it but she basically gets input from writing teams across Dropbox and UX writing but also marketing and customer experience, like all types of writing. And that’s a really big part of what we follow, but then we also have within that content style guide, we have part of it that’s specifically for UX writing, and that part is still under development for the past year or so.

That part of it is really cool to me because the different UX writers on our team, we have contributed different … We’ve created different rules and guidelines for different parts of the flow. Like, how do you approach error messaging? What do you do if you have a callout? How do you write the copy for that? It’s definitely a collaborative effort. It’s pretty fun. It’s a living document though. We’re still working on it.

Kristina: Living documents are always a joy. Exactly.

Angela: There’s a lot of words in Dropbox and Paper, so there’s a lot going on. We actually, we have a design systems team as well and we are going to be adding a UX writer to that team who’s going to take even more of a leadership role of the UX writing style guide.

Kristina: Let me ask you this. I maybe should have asked this at the top of our conversation but I’m going to ask it now. At Dropbox, where does UX writing begin and end? I mean, if there’s a set of guidelines within the larger style guide for UX writing specifically, what is that encompass?

Angela: Like how do we define it?

Kristina: Yeah.

Angela: I think we define it, oh okay I see. Maybe like in comparison to marketing writing or …

Kristina: Yeah, you mentioned you write error messages. What else is UX writing responsible for?

Angela: We’re responsible for onboarding messages.

Kristina: Within the product?

Angela: Mm-hmm.

Kristina: Yeah?

Angela: Yeah, exactly. We’re responsible for any labels in the UI like on web or desktop or mobile, and we have Dropbox and we have Dropbox Paper, that’s a lot. Let’s see, we write a lot of things. We write some email copy.

Kristina: You do?

Angela: Yeah, at least I do on Paper growth. We sometimes have emails that are about, that are sparked by user action. Maybe like someone’s tried out Paper and we will after a while, like a week or something, we might send an email suggesting that they invite other people they work with to try Paper and those are, they come from product.

We do work with product marketing and they do write a lot of emails as well, more that are about onboarding and kind of just selling the product. There’s a lot of overlap between some growth writing and product marketing.

Kristina: Right, right and that is always such an interesting thing, sort of attention within larger organization that exists I think … who is responsible for what copy and where, and I mean if it’s in the website, is it marketing? Is it UX? Because if it’s on the website, is it …

Angela: I think like broad strokes, we kind of define UX writing as anything that people see once they have logged into the product.

Kristina: Okay.

Angela: If you’re on the landing page and you have not signed in or you’ve not signed up, that’s all product marketing writing. Once you do, that’s kind of the UX writing world but there’re definitely places where there’s overlap though, like maybe you might see some prompts or something for a feature that you haven’t used and those might come from product marketing.

Kristina: That’s really interesting. That’s a good …

Angela: Broadly speaking.

Kristina: Right.

Angela: Signed out versus signed in. You’re signed in, then it’s UX writing generally.

Kristina: Right. Do you have the role of content strategist at Dropbox?

Angela: Content strategist is in marketing. The marketing team has that role but within the UX writing team we are all UX writers, we have different levels but we don’t have that role in UX.

Kristina: That’s interesting that there’s a content strategist that sits within marketing. What does that role do?

Angela: I don’t know enough about what they do actually. I need to learn more about it but I think …

Kristina: Or not. [laughs]

Angela: They do a lot of web content for our blog and landing pages. I’m sure they do a lot more. I’m embarrassed to say that ...

Kristina: Oh no. That’s totally fine. It is an ongoing conversation. It’s 20 years old about like what is content strategy. What does it mean with an org? What is a content strategist? What does it mean within each organization? I’m always just really curious to know like what is that title? What is that title? How does that exist?

This comes back around to something that I mentioned at the beginning of our conversation, which is that the title content designer has really taken root in the UK and throughout Europe and now in Australia as well. That is really very much focused on I think web pages, and potentially even within products, but it really is very focused on identifying user needs and getting to top tasks and prioritization of those tasks and so on.

Would you say that that role is, and if you don’t know enough about it that’s totally fine, but would you say that those two terms are kind of interchangeable or …

Angela: Content designer and …

Kristina: Yeah.

Angela: What’s the other …

Kristina: UX writer.

Angela: Oh, I think UX writing at least as it is defined at Dropbox is, it’s very product-focused. I hear you, like there’s definitely a lot of similarities there but maybe it’s like the surface ...

Kristina: Yeah.

Angela: Yeah, I mean we’re very embedded in …

Kristina: In product.

Angela: Our product specifically.

Kristina: It’s just so interesting to me to watch the different roles evolve and that they all, do they ladder up within content strategy discipline? I don’t know. Maybe?

Angela: That’s what everyone, yeah. The idea is that content strategy is a big umbrella containing all these roles.

Kristina: That is what I use as an excuse to talk to a lot of different people that I find really interesting and you were one of those people.

Angela: I’m happy to be under that umbrella.

Kristina: We are all under the umbrella. I now feel the need to like do some sort of storm metaphor but I’m not going to do that. I’m going to just leave it.

Angela: Leave it to the imagination.

Kristina: Hey, Angela, our time is just about up. I wanted to ask, if people are interested in hearing more from you, are you online somewhere that people can look you up?

Angela: I do have a Twitter account that I don’t use very often but I’m at @angiegorden on Twitter and I have a website AngelaGorden.com where you can see all of my connections and I sometimes might post different to what I call copy or UX crushes that I have.

Kristina: Oh cool.

Angela: Different things that I see in other products that just make me smile.

Kristina: You see you could put those on Twitter.

Angela: Yeah, I should do that.

Kristina: Because once again, my needs.

Angela: All right. I’ll work on that. I’ll start this week.

Kristina: Exactly, exactly. And we’re all going to be looking forward to your blog post on feedback, right?

Angela: Yes, I’m working on it.

Kristina: Again, first draft end of next week. Angela, thank you so much for joining me today.

Angela: Thank you.

Kristina: I really appreciate your time and good luck in your continued work at Dropbox.

Angela: Thanks so much. It’s been really fun.

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Kristina: You’ve been listening to The Content Strategy Podcast. I’m your host, Kristina Halvorson. This podcast is brought to you by ContentStrategy.com and Brain Traffic, a content strategy consultancy. Find out more about Brain Traffic at, of course, BrainTraffic.com. Thanks and we’ll see you next time.