Design Leader Insights - Alastair Simpson on Nonlinear Workflow at Dropbox

May 24, 2023


Alex Smith: Design leader Insights is brought to you by Fuego UX. Fuego UX is a user experience consultancy focused on creating simple and intuitive digital experiences. Hey Alastair, thanks so much for joining the show today.

Alastair Simpson: No worries. Thanks for having me, Alex, appreciate it. 

Alex Smith: Yeah, no doubt. And to get started, can you give the audience a bit of context in your journey in UX? 

Alastair Simpson: I didn't study design, like I didn't study design back in college, I did a lot of psychology and consumer behavior. So why people do things in general, like why do people buy things, like, what's the psychology behind that. And that kind of led into how I eventually got into design. But after university or college, as you call it, in the US, I got rejected for a bunch of graduate jobs in London. And so instead of going straight into the world of work, I went traveling around the world and started in South and Central America, went to Australia, Southeast Asia, a bunch of places and, and then ended up traveling for like, two years. And you know, I think we'll probably talk about this later on. But one of my first jobs was, you know, in a call center, which was super interesting, learning how to talk and listen to people. But then, yeah, eventually found my way into my first design job where I was a design team of one, I did everything branding, visual design, interaction design, I built my own usability testing lab using a piece of software called Moray, which at the time was like a huge investment of like, $2,000. So it was like, quite a big deal. But it was super interesting, like building my own little lab, having customers come in, having engineers watch customers use our website and not being super impressed. And just that was my, you know, kind of induction into design and just, you know, building products, testing them really early with customers building prototypes, shipping AV tests. And so that was how I started in design. And then, you know, eventually, over a course of almost two decades, I guess now, which is showing my age, like ending up at Dropbox as VP of Design. 

Alex Smith: That's awesome. So tell me about Dropbox. That's a tool, we use Dropbox Sign, at least. But yeah, tell me about that. I feel like that's a company that went remote and is still remote, which is interesting to me, as companies now shift back. But you might have been integral to that. So I'd love to hear about that.

Alastair Simpson: Instead of, I know that many companies, especially early on in the pandemic, they were, you know, wishing for the good old days in inverted commas to get back to the office, Dropbox took a very different approach. And kudos to Drew and to Mel our Chief People Officer for really thinking that, as seeing that as an opportunity, but they also invited me in to help leverage design thinking or human centered design, on how do you rethink work? Like, if you're going to redesign work from scratch, how would you do that?  And, you know, I quickly became the co-lead of what became our shift to remote work, which we called, we still call today, Virtual First. So it's not a hybrid model. It's not a colocated model. It's not a fully remote model. And I can talk about that in a second. But essentially, I became the co-lead of this effort. And I hired our first head of remote, we built out a small little team. And we approached it as a product almost with a human centered design mentality with our employees at the center of that experience. And so that's what I was doing for kind of two and a half years like redesigning, rethinking work, and happy to talk more about that if you want to Alex.

Alex Smith: What were those learnings of saying, you know, our team, these are the reasons why our team liked remote or virtual first as you put it? Or why do you think people are kind of like, going back to the office when in 2023 all this technology enables us to literally work from anywhere. 

Alastair Simpson: Yeah, I mean, individual companies will have their own policies, right? And, you know, I always say the same as building a product, right? Like you're always prioritizing or optimizing for something and trading something else up, right? And I think, you know, those companies are doing that because they believe their reasons are good for coming back to the office. And you may well be but focusing on us and our lessons. You know, we from day one, we had a few principles, one was to maintain a level playing field for our employees. And so for us, you know, hybrid doesn't necessarily necessitate a level playing field, right? If somebody is in the office versus has chosen to be remote, that's not necessarily a kind of level playing field. We also wanted to retain this kind of learning mindset. And so we said that whilst we were redesigning what we thought work look like, we didn't know all of the answers, like we didn't pretend to know all of the answers, but we said we would co-create and learn along the way with their employees. And we've done that. And the third was that we did believe that in real life or in person collaboration and meeting was important, right? We recognize the need to actually get people together. And so having those principles in place, looking at what was going on in the market, so just competitive analysis and what's happening in remote work, who are very future forward kind of companies, companies like GitLab to a fully remote, you know, what can you learn from those different companies. We set out then also understanding well, what doesn't work about work today, right? And if you think about what doesn't work is that it's nine through five, yet our lives don't work nine to five, right? We have childcare pickup, or maybe we're a caregiver, or actually, we're on a different side of the US. And so nine through five doesn't mean nine to five for me, right? So we set out with some early kind of hypothesis, just as you would as you're building a product. And one of the hypothesis was, we believe we needed to build a nonlinear workday. What that means in practice is, we have a set of core collaboration hours, that's four hour time blocks. So for me on the West Coast, that's nine through one, where I'm expected to be online for synchronous collaboration, or to respond to Slack or email in a very timely manner, right. But outside of that nine to one, I'm encouraged to create my own nonlinear workday, which means I can work and be productive when I feel like I'm going to be productive outside of my caregiver status or my kids, right? And so we encourage that, as a practice at Dropbox. We learned that employees wanted to change their habits, but they didn't know how. And so we did two very important things. Which one, we released something called the Virtual First Toolkit, which is public, anybody can go use that. It's about 20 to 25 practices, which are kind of step by step guides to help people unlearn habits around, okay, how do I reduce my meetings? How do I not reflexively just schedule a meeting? When should we have a meeting, right? When should we meet in person? So lots of different tips and tricks and techniques for how to change your habits. So we release that to the company and also externally. The second thing that I think was important that we did was we learned from this research that there were kind of five behavior changes that we were trying to adopt, right? And that that one around meetings is important. So when we shared these five behavior changes with our company, we said, this is what we're going from, and the from behavior was synchronous meetings all day. So that was what we were going from, to working asynchronous by default. Right? How do you encourage this asynchronous first, right? Can I resolve this in an asynchronous way? Whether that's via something like Dropbox Paper, JIRA, Slack is even asynchronous, right? Can I resolve this asynchronous before I moved to synchronous right? Before I moved to a kind of meeting. And so we had five different behaviors. But more importantly, we shared that because we said, hey, 3000 Dropbox employees, we're on a journey together, about changing our behaviors. This is where we want to get to, and these are some tactics, we had lots of different tactics and techniques for how to get there. But we said, this is where we're going and we want you to come on that journey with us.

Alex Smith: Alastair, I'm interested to learn advice you may have for new designers entering the field today?

Alastair Simpson: The job I had after college where I went traveling, and then I ended up in Australia for a year, and there was only really three jobs you could get in Australia on a short term visa, and it was either laboring, you know, one of those people in the streets selling, you know, trying to get people to sign up for charities, or it was working in a call center ,I opted for the call center route. But what I learned from that experience was just the importance of active listening. So actually listening to what people are saying, and then asking questions based on what they're saying, to uncover information. So that you can help either sell them a solution based on the problem that they have, or you can actually help them because when I was doing inbound customer service, you can actually diagnose the real problem they had, so that you could then actually, like help them. And so again, you know, translating that to design, actually, the key thing for designers is to understand the real problem from a customer. So actively listening, or the business, right, and then asking lots and lots of questions, so that you really uncover the true need, not just like the surface level need, and then having the communication skill to be able to tell a story back about why, you know, if you're selling something like why this thing is actually the right thing for it to solve that problem, or communicating in an empathetic way, if that customer is angry, or whatever they may be, because they've got they've got a customer service issue, but just the importance of communication. And so whenever I mentor people, you know, you know, for over probably 15 years, this is the number one piece of advice I give them is just really hone your communication skills and in communication, it's active listening and questioning, as well as being able to present a solid argument. And there's a great book out The Psychology of Persuasion by Robert Cialdini, and another one, Resonate by Nancy Duarte, which is the art of storytelling, which are two just I think, excellent books to really understand the importance of psychology and then storytelling in you know, when you communicate trying to communicate something. And so that's the thing that I would totally advocate for people, you know, any designer to go learn versus the heart, you know, the skills in Figma or Framer, or whatever you're using. It's like, yeah, that they are important. But communication is critical in my mind.

Alex Smith: That's some interesting, maybe unconventional advice of like, sales has a lot to teach you about communication in general, whatever your role is. So I love that. 

Alastair Simpson: That's right. I mean, if people search, I've got a Medium article where I break down a popular sales technique, like framing technique, and show how you can use that when you're presenting design work, because it's basically the same thing. It's like, what is the problem? You know, how do you uncover the need? What is the real need? Like how do you then present your solution in a way and then how do you close in a way that seems like professional and is actually going to, you know, solve the problem in a really neat way? So yeah, there's, it's I don't know, as I said, I think it's critical.

Alex Smith: Yeah, there's an eerie overlap there that I think is awesome. Thanks for sharing that. And thanks so much for coming on the show today. 

Alastair Simpson: Thanks to you for having me on and thanks to everyone listening.