Writers of Silicon Valley Podcast: Roy West transcript

Writers of Silicon Valley is a UX writing podcast featuring interviews with content strategists and UX writers from around the world.

The UX Writers Collective is proud to host transcripts for every episode.

Roy West heads up UX writing at Uber. But his career spans decades, featuring stints at NeXT and Google.

In fact, Roy was one of the first UX writers on the Android OS.

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Patrick:

I’d love to hear about your career history and I’m really interested to understand how you got into this work in the first place.

Roy West:

Sure, so I started in trade book publishing. I got a job in the early ’80s when I moved to San Francisco with a book packager called The Compage Company, which was run by a fellow named Ken Burke who partnered with a printer to package editorial, production, and printing for a variety of different companies. 

They focused on how-to books. So he had a very popular physics textbook that he kept after he left New York publishing and came out west, and they sold the idea of how-to books on a number of household and gardening and small construction projects kind of how-to books to a couple of different folks. 

They did work for Sunset Books. Sunset is a western lifestyle magazine based in California. They sold the idea of Ortho books to a garden, chemical and household products company called Ortho that was part of Chevron, and invested that line of books that were very popular for a while.

Roy West:

They also did work for Time Life Books. So there was this milieu of knowing how to produce books that taught people how to do things. 

And then as the computer industry was beginning to try to reach out to a popular audience, they looked for people who could help them teach people how to use computers and they turned to Compage and places like that to help them build out the ability to create user education in book form.

Roy West:

I started in this company answering the phone and typing on a CPM machine with a teak case because they wouldn’t have an ugly PC in the office in the early ’80s. 

And I learned a good deal about how that kind of book is made and about how editorial is done. I learned how we have hundreds of years of tradition and process for how to produce something that’s pretty close to perfect in terms of quality, for very little money through strategy, division of labour and things like that through the editorial process. 

Through printing and production know-how. I was there for about five years and at the end of that time I was responsible for a series of book projects for Apple and other vendors and I had a writer quit, and I thought, “You know what? I want to write this.” And they couldn’t keep me on as a writer so that’s where I switched over to writing.

Roy West:

That was really where I began working as a technical writer at Compage. And later what I learned was to look at the software and not at the book in terms of the first place to try to fix things. 

So at Compage the very talented editors I worked with were consulting with these computer companies to say, if you did this differently with your software, it might be easier to use. And that was really my entry into a career working in documentation, but also that was focused on looking at the product and using an editorial and developmental editorial eye towards bringing coherence and consistency to user interfaces as frequently as part of an engineering team—an embedded writer in an engineering team.

Patrick:

That’s very early for that type of work because I think a lot of people tend to assume that technical writing is something that happens post-fact. So something is created and then technical documentation comes afterwards. But as you say, that’s a really interesting early example of how those two things can be integrated together.

Roy West:

Sure. Though, it’s actually an idea that’s been around for a long time. There was a very popular programming journal for the Macintosh community called Doctor Dobbs Journal in the ’80s, and there was an article that struck me once at the time.

 The argument was you should write the documentation first and then design your product. The idea being it would allow you to think in a coherent way about what’s the functionality, how does it fit together and how does it serve a user by basically working on the documentation, and then back to the user interface, and then back to the code.

Roy West:

And I think that informs a lot of what many of us on the UX writing side of things think of, right? Is how can we bring that editorial and writing skillset to bear for thinking about how to design products.

Patrick:

It’s such an interesting time, too, in San Francisco at that time. So what was the vibe like at the time? What was it like during that time being connected to that industry?

Roy West:

I think that in the early ’80s the tech industry was still much more influenced by the sort of the previous generation of engineering. And the hallmark of that was I found I was working with products that didn’t quite work. 

All kinds of hardware and software that we take for granted, all the kinds of communications things we do now, but at the time we were struggling with modems and pinouts on cables to make our computers talk in the most rudimentary way, to bulletin boards using telephones as the way to connect the computers together. 

There was a much more of a handmade aspect to it, and I think that the reason I bring this up is one of the things that struck me about dealing with engineers in these companies, was an enormous generosity of sharing know-how that I still remember quite clearly and shapes my view about how we work together.

Roy West:

I can’t tell you how often somebody at some company would take the time that they didn’t have and very patiently walk me through how to solder up some cable in order to get the computer connected to the phone, right? Or things like that.

Another thing I’ll say is that I think we’re compressing some events. I think that there was a great deal of work in between the excitement, so we mustn’t compress too much. There was also a great sense of optimism about the potential for connected computers. 

Also, for desktop publishing, we don’t think about that technology much anymore, but for technical writers it was influential. For the way we all think about the world, what turned into the web, that going back to the laser writer and some of these page makeups products that morphed into the tools that we also now use to create web pages and blogs, right? 

There’s a lineage there. There was an enormous optimism about the potential for putting the press in the hands of the people, if you will, right?

Roy West:

You’ve got to remember, I live in Berkeley, so some of that political world view rubs of. But I very much shared that view about a democratizing influence of technology, both in terms of know-how and that generosity, but also about the potential for technology to empower people.

Patrick:

When you think about empowerment, it seems like the way that technology has changed over the past 30-35 years has, in some ways, it’s kept that democratized spirit and in other ways, it’s become a lot more patented, a lot more boxed in, between not only companies but engineers and even writers perhaps. 

What do you see as having changed in that time? Do you still see that spirit of democracy in San Francisco in the tech industry?

Roy West:

I do, and I think you can read online far more informed people than I am on this subject, but I’ll say that certainly the spirit of a place like Google or even a place like Uber now, where I am, is viewing technology as a tool for empowering people. 

But at the same time, just in the past couple of years, all the implications of that technology are becoming more visible to us in ways that you and the people that would listen to this would be very familiar. 

What’s happened at Facebook. What’s happened with Twitter. Should Google go back to China? Or the implications of that or not. 

What are the implications of the great firewall and similar kinds of internet censorship, which happens in many other countries. Also, what are the implications of anyone being able to spin up a website like Info Wars and have a profoundly divergent view of the world that in many cases people view as quite destructive.

Roy West:

That is utopianism in a way. We’re all looking very hard at that and trying to grow up a bit about how we think about it. But the idealism I don’t think is gone, it’s an idealism that’s realizing that it has to grow up and figure out: How do we act responsibly also?

Patrick:

Yeah, I completely agree. So you’re in the ’80s, you’re creating this technical documentation and then after that sort of period, where do you go next?

Roy West:

Where I went next was to NeXT, to the company that Steve Jobs founded after he was forced out of Apple. And I joined there shortly after the Cube was released. It had just acquired a magneto-optical drive. 

The modern wonder of the world that it was. And I went in there as a contractor working on user documentation and then converted and stayed on there for about five years, working on system administration documentation and also user documentation. 

And then we also worked very hard to take what we had learned from folks who came out of Compage with me and others about accessible, task-focused user documentation and convert that into usable online help. 

And we were sort of pleased with our system and then we began to see this thing called the web and we realized that actually HTML was clearly the way to go with that. 

So we threw all that away and re-implemented it all in HTML and that was sort of an early use of HTML, was to power obviously many things on the web, but also online docs, online help.

Patrick:

How did you even come to NeXT in the first place? Was there someone there who you knew or was there a job opening?

Roy West:

There was a job opening and I interviewed with a woman I’ve worked with since, a brilliant writer named Helen Casabona, and also a really innovative technical writer and editor named Caroline Rose, who had been instrumental in the inside Macintosh work, which was sort of groundbreaking developer documentation that actually had touched at Compage as a consultant. 

Patrick:

NeXT was a big company by that point and it had processes and there were lots of people and it was a fast-moving train, I would have imagined.

Roy West:

Yeah. I would say. So, I think what Helen and I, a brilliant editor and writer named Cathy Veeon who I introduced to them and who I met at Compage, brought to NeXT was thinking about user documentation and user education in the ways that I had learned at Compage.

Much more text, sort of thinking about tasks and reference, how they fit together. A much more telegraphic style. A much more visual style of presenting information that you still see on the web, I mean the roots go back to this.

And at the time, NeXT was very academic-oriented and so it had created thick textbooks that were the documentation for both how to use the product, how to code, and also how to use the tools that they’d built.

Roy West:

And I think that what we did there was move over to the Mackintosh style of graphical layout, of using graphical design to serve the editorial role. Which I torment my design friends from time to time by reminding them that of course the role of graphical design is to serve editorial.

And I would certainly try to take advantage of extraordinarily gifted graphic design at NeXT. So Jeff Jaksic helped with a really modern and groundbreaking approach to the laying out user education in printed form. And then as I say, through RTF and then HTML, these online help forums.

Patrick:

Was there any pushback to the type of work and approach you were taking? Or was it very much everyone getting onboard?

Roy West:

No, and I would say one of the things I consider myself most fortunate about in my career is that at NeXT, at Be, at Google, at Uber, I’ve gotten to work with just extraordinarily intelligent people. And people who may have had egos, but they also knew how to listen and see good ideas and run with them.

And there may have been some questioning about shifting away from that sort of funny text book format, but I think that when people saw what we were proposing, that the common sense appeal of it won people over. Because they were intelligent enough to understand what the goal was and what it was achieving. So I would say no, there wasn’t a great deal of pushback.

Another hallmark of these places that I worked, and again I feel very fortunate in this way, is that there was a culture of people figuring out what the right thing to do was and maybe ask some hard questions, but there’s not a ton of second guessing.

Roy West:

Now that may happen in some areas to some people, but that hasn’t been my experience. It’s that if you do good work and you can speak to it and speak intelligently to the reasons why you’re doing it, there isn’t a lot of sort of inappropriate pushback. There may not be support, there may not be funding, there may not be wild endorsement, but people aren’t telling you no, you’ve got to go do this some other way.

Patrick:

Was that partly Steve Jobs’ influence? Because his approach was very much common sense and being accessible. Did that filter through to the type of culture there? Or was that something that was sort of like an organic industry based change as well?

Roy West:

So the Macintosh was really quite ground breaking in how they approached user education. We had inherited some of the success of the Macintosh as an approachable platform. And that meant not just the user interface but also the way the user education worked. I worked with a fellow named George Truitt, Cathy Veeon, Carol Wesper, some of these other folks at Compage on how to teach people how to use a mouse. How to edit text with a cursor. A lot of that we take for granted now.

Roy West:

That we would need to teach somebody how to do that, but there were pages of the original Mac dedicated to how to do that stuff. To teach people how to do that. And it worked, right? And so by the time we got to NeXT, there was an openness to understanding that there were ways of teaching people how to do things that were not dense text.

Patrick:

And I think you see that when you get to Google. I just want to speak about Google particularly, because you were there for quite a long time. I think about eight or nine years, is that right?

Roy West:

That’s nine years.

Patrick:

I’m interested to hear you talk about that time in particular at Google—was there that drive to really make things as accessible as possible? What was the guiding philosophy for the type of writing there? Because that’s really when you start moving from technical writing into what we would now call UX writing. Would that be fair to say?

Roy West:

That’s right. So let’s split technical writing into two pieces. One is writing for developers, teaching developers how to code. Not teaching them how to code, but teaching them how to use libraries or languages that are new to them, for a specific purpose.

And the other is a broader audience on how to use software to accomplish tasks. In between there somewhere is a system and related topics.

Roy West:

So I’d been at these companies that were at the forefront of user interface work. And then I ended up for over five years at a company that was producing a virtualization software for servers and networks.

Dial up a bunch of servers to do one thing in the morning and then have a code that you could graphically set this up to dial those down and then turn up the accounting, number crunching at night. It was very innovative, but it was a tiny little company.

There was very talented UI folks there. Eugene Walden, a few other folks, but it was removed from the world. So it came to the end of it’s life and an old friend of mine said, “You know there’s this Android team at Google who need someone who does exactly what you do.” 

Roy West:

I went into the Android team in 2009 and while I was out, the world of UX design and the world of UX research had really flourished. And so I came into an environment that had dedicated user experience design, interaction design, visual design research as recognised established disciplines.

And that was a huge eye opener for me and an enormous education. I had been director of UI at my previous company, but I was now working with these folks who had really studied UI in a formal way and I realised I had so much really to learn from them, even though I had much more industry experience.

Then the battle was: Where does writing fit into that? I was hired at Android to write user documentation, but also to be responsible for the text in UI and I kept both of those things going for a couple of years before I got recruited over to the product that was going to turn into Google+.

Roy West:

Increasingly the UI became the focus. And then for me the switchover to full time doing that was in 2011. But keep in mind, that had been my role at all my previous companies. I always sought jobs that were in engineering, not in marketing or other areas of the company, so that I would be hands on with engineering and with the product.

And I found that collaboration between writing and creative and engineering creative hugely rewarding. And in fact it’s something I worry about now with the rise of the product management culture.

There’s now something of a barrier between design and engineering that I don’t think is healthy.

And I think we need to rethink how that works, because as much as I admire and appreciate the role of product management, that connection is getting broken and I don’t think it’s healthy for the product.

Patrick:

Yeah, agreed. It’s a really hot topic in UX circles right now: How do you write as designers collaborate and how do they join together?

Because I often speak to younger writers who will call themselves a UX writer, but what they’ve done is copywriting before and they haven’t worked with a UX team and now they’re calling themselves the UX writer because they think it’s going to be easier to land a job.

They don’t actually have that collaboration between the two disciplines.

Patrick:

So was that a breath of fresh air for you or were you having to really rethink some of the ways you had been working previously?

Roy West:

I was very accustomed to working with engineering to make user interfaces more intuitive and selfishly easier to document. The thing that caught me by surprise and ultimately was so rewarding for me was to discover that you could study interaction design as a discipline and become really quite adept at it in a way that I really realised I was almost an amateur at, even for all the years that I’d been working with UI folks and such.

But I would say that certainly at Uber the way we’ve been trying to articulate this, is that the writers on the product design team are designers. And they need to understand that their first role is partnering with design and research, who are also designers, to create product.

And that means that the most fruitful teams, and I saw this at Google as well, is where we have writing and design and research tightly bound together, working together—travelling to do research together, looking at mocks together, talking through from ideation, through looking at logs after you ship.

Roy West:

They’re all working together with their particular strengths they’re bringing to the table, but becoming extremely familiar with the disciplines that they’re partnering with.

So a writer who is not thinking that their words are in service of user intent and of a flow that is designed to facilitate accomplishment of the task in as an intuitive and friction free way as possible is missing the point of what we’re doing.

I would say what’s hardest for people who come out of marketing and places like that—where the words are about selling. The words are drawing attention to themselves in order to make a connection with a reader. Whereas with UX writing, frequently, we’re trying to hide. We’re trying to create a use language to create this frictionless experience where you don’t even realise you’re looking at the words.

You’re not reading anything, you’re intuiting it just as you intuit the grace of the visual aspect of the graphical design in order to accomplish your task.

Roy West:

And you get your task done—you didn’t even think about it. That was what was delightful. You didn’t have to stop and ponder, “what do I do?” It helped you get the thing done and you’ve moved on.

Patrick:

Exactly. I assumed this was the norm in a lot of other companies. But speaking to other UX writers, unfortunately it’s not. They’re great UX writers, but for whatever the reason, their culture just doesn’t allow them to, for instance, be involved in the research.

Or walk with the designers alongside designing something. So they end up getting a design, having to write for it, and they haven’t seen it before.

It’s unfortunate really, and I really hope some work is done into the next few years to change that. Because as you said, the most fruitful teams are the ones that are collaborating the most.

Roy West:

Well let’s talk about what fruitful means. Fruitful means these are products that are successful. That will be successful on the market. And so I think this will be self correcting over time.

People can stick with certain ways of doing things, but the better ways of doing things that produce better, more profitable products, just to be blunt, more successful products, those are the ones that are going to be successful as companies.

And it’s just crippling to be asked to come in to look at a design after it’s been done and they say, “Please, we’re having trouble with this part of the flow. Could you rename this button?” Frequently, there is no writer in the world who can solve that problem with writing.

It’s a fundamental flow problem that the writer being involved earlier might have been able to help with, or might have been able to point it out, if they would have discovered earlier that it wasn’t solvable by just renaming a button. So that product is not going to do well. That team is not going to do well.

Patrick:

That problem was three steps ago. And I find this sometimes, even UX writer circles, where we adhere to these principles and they’re almost taken as laws, but sometimes they don’t provide the best experience.

One of the things that I always brush up against is the principle that UX writing should be as short as possible, as snappy as possible and just the fewer words the better.

On the whole, that’s absolutely correct. You don’t need five words where one will do.

But sometimes it does lead to this miscommunication between design and writing where design will not allow for a particular block of text where actually four sentences might be appropriate together with a headline that might summarise what you’re looking for legibility.

Patrick:

So it’s interesting these little schisms pop up every now and then that I think we just need to be cognizant of. But you’re absolutely right, this should be self correcting over time, I think, but as to how long that takes, I guess we’ll have to see.

Roy West:

Yeah, and I think you’re right. So Sue Factor came up with this phrase and this fabulous internal document that I wish were available outside of Google called “Short Beats Good,” which was this first explanation of how to think about UX writing.

A really groundbreaking document that, again, I wish was more widely available. But we have these rules that are developing about brevity, about always being in the present tense. About all kinds of things like that.

But I believe we are really at early days of really understanding what best practises are for all the writing for all the different kinds of user references. And this is where being wedded to our research partners and learning more about research and how to conduct our own research.

This is one of the main things I’m driving with my team and with my partner in research at Uber and is to be more tightly coupled with research.

Roy West:

I saw that happen repeatedly at Google where we thought that by being as pithy as possible.

We knew that that was successful as a rule, but then at certain key inflexion points with very visible, very prominent moments in Google products, discovering that adding some little more text, a little more explanation, a little more information, even much more information, produced a better product.

So again, we have these guidelines. I don’t think we’ve tested them very well. I think on the whole they’re good guidelines. They’re well thought through, they’re reasonably effective, but we don’t really know.

Roy West:

And it’s something that I’m excited to work on in the coming year or two is to get a little more rigorous about how we measure these things.

Patrick:

I think it really depends on the product, the team and the culture. One of the things that I’ve spoken to UX writers about is if you look at job ads, more companies looking for UX writers are looking for people with a journalism background and my background is in journalism.

I used to be a business journalist. And I actually think there’s a lot of crossover because in journalism 90% of what you’re doing is research.

The writing only comes at the very end. I can bang out 2,000 words in a couple of hours. That’s really not a problem. But if I haven’t done the three weeks of research beforehand, I’m not going to get anything done.

Roy West:

So you’re pushing one of my buttons about what’s the right background for a UX writer.

Patrick:

Okay.

Roy West:

Journalism happens not to be my background, but this is a young enough discipline that when we’re hiring we can’t limit ourselves to hiring people who’ve done exactly what we need before.

Patrick:

Exactly, exactly.

Roy West:

Ten years from now it’ll be a little bit different, but that isn’t the case now and it certainly wasn’t the case five years ago, and I’ll say that one of the richest sources of UX writing talent in my experience, was from journalism.

And I’ve given a good deal of thought about that. Two of the most talented leaders in UX writing at Google right now, one came out of the L.A. bureau of the Washington Post. The other came out of New York magazine publishing. Martha Stewart Living, that sort of thing.

Brilliant, brilliant writers. Very thoughtful both on the strategy side and then on the sort of focused execution side. And so, why?

Roy West:

I have to go back to my high school English to what they taught me about journalism.

That you have a pyramidal or some say this inverted pyramid structure of information which in UI we call progressive disclosure. And then you’re structuring your content so that on a newspaper, the headline, you can read the headline on a newspaper that you read often, and frequently you don’t need to read the article.

And that’s so related to titles and buttons and things in UI, right?

It’s that we come up with this vocabulary and sort of idioms that reveal what’s behind there without the words really giving you that much information.

And then the first sentence, first paragraph, that’s diving in deeper into a UI where you get more context for a specific task.

Roy West:

They’re also used to dealing with horrible space constraints. And they’re used to not owning their own copy so their language isn’t precious. Some editor is going to re-write it and that’s just fine and it might be better.

So they learn how to collaborate as writers and they also know how to ask the right questions and keep asking until they feel that they’ve proved to themselves that they understand the topic well enough and the issue well enough to be able to explain it to other people.

And then at some point they were an intern and someone forced them to memorise AP style or Chicago manual or some other reference so they’ve really got the nuts and bolts of how to use punctuation, all that stuff. In tech we rarely have an editor to work behind us. We have to know that stuff to be able to produce polished work.

Roy West:

So all those things together is a training ground and a mindset that I think is a very rich source of the kind of thinking that we’re talking about. So then the big leap is: Can you take that and transition it from telling a story about an event to telling the story of a flow, of a process? And I see people make that jump. Not everyone can, but I see people making that.

Patrick:

Yeah, and I think one of the other things that really helps is being able to identify and interact with multiple different sources of information. That could be researching documents, it could be talking to people, it could be data. And then I need to evaluate those sources and decide which of these am I going to emphasise for this particular story? And in fact, sometimes, which am I going to disappoint because I’m not going to provide the story that they necessarily want to.

Patrick:

For instance, that source could be internal stakeholders who you may have to disappoint because you’re going to have to emphasise certain sources, perhaps data or the results of an AB test or so on in your product design, in your writing.

I think that’s another element that journalism can really provide. And it’s just interesting that you mention all this, because I have seen this trend growing recently and I’m interested to see if more journalists jump on, particularly as the job field there becomes, unfortunately, more limited.

Roy West:

Yeah, I’ll say one other thing about journalism—about good journalism—is that learning how to write, in spite of what I said before about having your language disappear, there really is a lot to be said for learning how to write in a way that charms and is positive and that sells.

And I don’t mean in an overt, hard sell kind of way. But when I think about the newspapers that I gravitate to as a compulsive news reader, they’re newspapers like The Washington Post where the writing is so graceful and so elegant and sometimes funny or arch.

But it’s giving me the information that I need in a way that is a joy. That it’s a pleasure to read.

I often talk to people about the need to be positive in a user interface and the way that you know people who are negative and how it’s kind of a drag to be with them, and people who are relatively positive and tend to uplift your mood.

Roy West:

So in that same way, people understanding that newspapers sell because people want to read that stuff, right? And whether it’s now moved online or not, very dry, uninteresting writing does not grab readers. So I think there’s something there from journalism, as well.

Patrick:

For anyone who’s wanting to get into UX writing or for UX writers now who may have a lot of experience, what’s something they should go and read? Something that’s perhaps given you some value as to how you improve your writing or the way you think about content and content strategy? 

Roy West:

A book that I just thought was just fabulous and timely is this book Conversational Design by Erika Hall that’s from a little press called A Book Apart. I think that she just encapsulates at just the right level a lot of what’s going on right now in thinking about the role of language in user interfaces.

About the role of thinking about this conversational design, which I think is not a new idea, that you would use conversation as a metaphor or as a tool for thinking about the flow of a user interface, but I think she just does a wonderful job of talking about how the discipline of voice UI design and then just thinking about conversation and it’s role in user interfaces in general.

Roy West:

I think any UX writer who wants to have confidence in being employed five years from now had better understand what conversational design is about and what the implications for voice interfaces and chat interfaces are about.

I think that this is a technology that we know that this is going to be an essential interface and omnipresent interface sometime soon. I think we’ve been saying that for 20 or 25 years, but it still is true.

Roy West:

Well I’ll just give you a metaphor about this. I have a hobby, I’m very interested in botany and I work with people who are combating invasive weeds.

A woman I know who is very knowledgeable about ecology and botany said, “You know, the funny thing about weeds is you’re out in the field and you see a certain weed year after year, you say huh, I saw that one this other place. You see them in singletons, right? And then suddenly they’re everywhere.

And there’s something about the way weeds invade that it seems like they’re not there, they’re not there, they’re just here and there, and suddenly they’re everywhere.”

And I think we saw that with cell phones a few years ago and I think we’re going to see that with voice user interfaces soon. It’s sort of here and there, sometimes it’s a little more established here but suddenly we’ll look back and we’ll be shocked that somewhere there was a time before this.

Roy West:

And we as writers and we as people who are creating a bridge between product and the things that you do with the product and people who are trying to get them done, conversational spoken chat based user interfaces are around the corner.

Patrick:

Fantastic. Well Roy thank you so much for joining me on the podcast. I really appreciate your time. And if people want to come find you or follow you online where can they do that?

Roy West:

Well I’m not very present online, I’m afraid. I am on LinkedIn and I do post there occasionally.

Patrick:

Don’t connect with Roy if you don’t know him. Just read his articles. Don’t be intrusive. Roy, again, thank you so much for your time. I really appreciate it.

Roy West:

Thank you very much, Patrick.

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