Insights Unlocked
Effectiveness vs. efficiency in design with Dropbox's Alastair Simpson
Mon, 17 Feb 2025
Episode web page: https://bit.ly/3CBgLhw ----------------------- Rate Insights Unlocked and write a review If you appreciate Insights Unlocked, please give it a rating and a review. Visit Apple Podcasts, pull up the Insights Unlocked show page and scroll to the bottom of the screen. Below the trailers, you'll find Ratings and Reviews. Click on a star rating. Scroll down past the highlighted review and click on "Write a Review." You'll make my day. ----------------------- In this episode of Insights Unlocked, host Jason Giles sits down with Alastair Simpson, VP of Design at Dropbox, to discuss his non-traditional career journey, scaling design teams, and the evolution of remote work. Alastair shares key insights on fostering a strong design culture, navigating hypergrowth environments, and leveraging AI to enhance UX research. Tune in to learn how Dropbox’s Virtual-First model is redefining collaboration, why outcomes matter more than process adherence, and how AI is reshaping design workflows. What You’ll Learn in This Episode 🎨 Alastair’s Unconventional Path to Design Leadership How he transitioned from aspiring professional footballer to UX design leader. The role of consumer psychology in his design approach. How early career experiences—like working in a call center—helped him develop core design skills such as listening, communication, and problem-solving. 🏗️ Scaling Design Teams in High-Growth Companies Lessons from leading design at Atlassian and Dropbox during rapid expansion. Why effectiveness matters more than efficiency when managing creative teams. The importance of regular critique and how Dropbox ensures continuous feedback. 🌍 Virtual-First Work & Remote Collaboration How Dropbox designed and implemented its Virtual-First model (90% remote, 10% in-person). The concept of "core collaboration hours" and why nonlinear workdays boost productivity. The impact of remote work on trust, culture, and cross-functional collaboration. 🤖 AI’s Role in UX and Research How Dropbox is using AI-powered agents to improve access to past research. AI’s role in summarizing usability studies and enhancing design iteration speed. The balance between automation and human judgment in crafting great experiences. Key Takeaways & Quotes 💡 “Design is about building strong foundations—color, typography, layout, and interaction design. AI can enhance our workflows, but it doesn’t replace good fundamentals.” – Alastair Simpson 💡 “We don’t focus on efficiency for efficiency’s sake. Instead, we prioritize outcomes and impact.” 💡 “Virtual work doesn’t mean no in-person connection—it means intentional gatherings that matter.” Resources & Links 📌 Connect with Alastair Simpson on LinkedIn 📌 Learn more about Dropbox Design: Dropbox.Design 📌 Explore UserTesting: UserTesting.com
Chapter 1: What is the main discussion in this episode with Alastair Simpson?
Welcome back to the Insights Unlocked podcast. In this episode, we're sitting down with Alistair Simpson, Vice President of Design at Dropbox. In his conversation with User Testing's Jason Giles, they talk about effective versus efficient design, scaling design teams, leading in a remote-first world, and the role of AI in design and research.
From his unconventional journey to design to the lessons he learned at Atlassian and Dropbox, Alistair shares insights you won't want to miss. This is a longer episode, but I promise it's worth your time. Enjoy the show.
Welcome to Insights Unlocked, an original podcast from User Testing, where we bring you candid conversations and stories with the thinkers, viewers, and builders behind some of the most successful digital products and experiences in the world, from concept to execution.
Welcome to the Insights Unlocked podcast. I'm Nathan Isaacs, Senior Manager for Content Production at UserTesting. Joining us today as host is Jason Giles, UserTesting's Vice President of Design. Welcome, Jason.
Hello, everyone. It's nice to talk to you again there, Nathan.
Yeah, nice to talk to you as well. And our guest today is Alastair Simpson. Alastair is the Vice President of Design at Dropbox, where he leads a talented and diverse design team across brand, product design, writing, and research. He previously led the design team at Atlassian.
Welcome to the show, Alastair. Thanks, Nathan. And thank you, Jason, for having me. It's a genuine pleasure to be here.
Alistair, I'm super excited. I will be honest, I've listened to a lot of your other podcasts and kind of followed you. As we talked before the show, we actually know a lot of similar people. So it's great to kind of make this connection. So I'm really thrilled about this chat. To kind of get things rolling, you have had a really fascinating career and introduction into the whole design world.
So I was hoping maybe you can talk a little bit about that unique background and then what initially drew you into design.
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Chapter 2: How did Alastair Simpson transition from aspiring footballer to design leader?
Yeah, of course. And as we talked about before the show, like it's such a small world in design, isn't it? It's crazy. It's crazy. Like the people, the connections you have, maybe we'll shout out a very, very close connection later on that we both know very well. But, but no, I mean, when I talk a lot, I was recently at SCAD and,
The College of Art and Design in Savannah are talking to students about this who are studying design. I mean, I've got a very nonlinear career path in design. I didn't go to a College of Art and Design and then take an intern job in design and then work. work my way up like that didn't happen for me.
You know, when I was growing up, I actually wanted to be a football player or a soccer player for people in North America. But I hail from England where it's called football. And I wanted to be I wanted to be a football player. And I was at a professional club until I was 16. And then I didn't quite make it as 16 in England is when you get your first professional contract.
And I didn't quite make it. I didn't make the cut. I did continue on playing though. I played semi-professional football until I was 37. And I always say that I quote unquote retired. It sounds nicer than had to give up because of various injuries. But I played elite level sport for a long time, but at 16,
I, you know, my dream was kind of over and that was genuinely really hard when you've worked at something like I played football every single day, sometimes multiple times a day at training and practice and games for different clubs, representative teams, the professional club I was at.
And when, you know, you have a kind of big disturbance like that, where you've worked so hard for over a decade for something, and then you realize that it's not going to happen.
Especially so early in your career. Yeah.
Yeah, that's right. So early in your career that it's probably not going to happen for you. That, you know, makes you pause a little bit. And honestly, at 16, you know, I probably didn't have the right coping mechanisms or the right frameworks to understand how to deal with it. And I was probably a little bit lost for a while.
I went to college, which is not American college at 16 to 18, which is kind of a bit of high school. I studied different things like English, psychology.
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Chapter 3: What lessons did Alastair learn from his global travels and early career?
I, again, we talked about, you know, such early disruptions. At the end of my university career, I applied for graduate jobs in London where I was living and I got turned down by all those graduate jobs. So, you know, my older sister had got a graduate job and she'd bought a house and she was doing really well. And a lot of my friends were like getting jobs.
I got turned down from the jobs that I applied for. And again, that was a big setback. But I ended up, I went traveling with my best friend. My best friend Adam was like, hey, I'm going to go traveling around the world. Do you want to come? And I was like, well, that sounds like something I would usually say no to, but sure, let's try that. And so, you know, I saved up money for six months.
I worked at JPMorgan Chase Bank, like doing some data entry and everything. Saved up money living at home. And then I flew. My first stop was Rio de Janeiro in Brazil for Rio Carnival. And then I spent a year traveling around the world in South America, Australia, New Zealand, Southeast Asia. And in those the traveling moments, I learned about.
being adaptive because you drop yourself into cultures that you don't know and languages that you don't know and you're immersed in it you have to learn how to deal with those volatile and certain ambiguous environments and how to integrate really well and you do a lot of that through listening being curious being genuine which again we'll talk a little bit about in a moment but
But then at the end of that year, I went and lived in Australia for another year. I didn't want to go back to England and get a real job, a serious job. And I lived in Australia and I worked in a call center. which is like, again, this is where I actually say my design career started. Because if people haven't worked in a call center, it's really hard. I think it's very interesting.
But you learn one of the most important skills of design, which is listening, asking questions, and then being able to effectively communicate. Because when a customer is on the phone with you, irate often, you have to be empathetic. You have to listen. You have to ask questions to uncover the true need, the true problem. And then you have to be able to communicate an effective answer.
And again, if we parallel that to design, we can design anything we want. Like we can make, move pixels around automatically. Now you can move pixels around to design anything we want, but, and it's like, is that a good solution? It's like, I don't know what the problem is. So I can't tell you if this is a good solution.
And so you have to ask questions and listen and really get to the problem beneath the problem before you start designing and then be able to effectively communicate. Because again, I, I see this in design critique and design reviews where sometimes designers cannot communicate and articulate their idea in a really solid way.
And so that's where I learned those other important facets of design, which is listening, asking questions, and communicating.
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Chapter 4: How did Alastair Simpson start his design career at Reed Business Information?
in order to expose myself to very different things and see where that takes me that was an intentional decision the working in a call center thinking i'm going to learn all these foundational skills less so but it was certainly on reflection uh looking back at that time because i do reflect most years now that that i really and then having worked in big technology companies and agencies
it's only then when you look back that you realize, okay, that I was learning a lot there. And those skills are really important to me now. And I'm very grateful to have had those experiences versus a traditional linear career path in design, which again, there's nothing wrong with that linear career path at all, but I'm grateful for my own journey.
And, and then, you know, just to round it off the initial journey into design, like,
Yeah, I was wondering, how did you get from the call center out?
I was just trying to work in Australia. That was the honest thing. I wanted to stay in Australia. Having grown up in England, Australia is a lovely way of life. And my first job was a B2B publisher called Read Business Information, which is part of the LexisNexis group or Read Elsevier. At the time, Read Business Information was the largest B2B publisher in the world at the time.
And they published magazines in industries you would never have heard of, like manufacturing and architecture and pharma. They published a magazine called Farmers Weekly, but had these huge distributions, you know, huge, you know, but they weren't, you know, GQ or something, right? They weren't these consumer magazines, right?
Obviously in the early 2000s though, print publishing was declining rapidly and revenue was declining rapidly. And I worked in the digital division in Australia of this B2B publisher where we were transitioning print revenue and print content online because the online revolution was happening. We were transitioning it all online.
And so I was part of this huge company, but I was in a digital division of 10 which was operated as a startup. And we grew to 150 people to, we went from zero to double digit millions in revenue in two years. Like, so we went through this hyper growth and I was the first designer there. That was how I got into design. I was the first designer.
And I was doing everything, brand, visual design, interaction design. I built my own usability testing lab using Moray software. Oh, Moray. Moray, that's right.
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Chapter 5: How did Alastair contribute to and learn from high-growth environments at Atlassian and Dropbox?
I mean, because you forget that back in those days that that was what it was. You used to have to go to the LexisNexis directory to download the information. That was how you got your information. It's changed so much.
Oh, 100%. So was it a read?
That was the name of the... Yeah, it's RBI, Read Business Information. That's where I initially started. Yeah.
And then you went on to go and just build some amazing teams at Atlassian and Dropbox. Was that just an opportunity again, or was that proactively like, hey, here's what I want to go pursue?
Yeah, these were definitely more intentional. I mean, in between those things, so I finished at Reed, and then I actually went traveling again for a year. I traveled around South and Central America. for a year and that was wonderful. It was really great. I'd saved up money and we just went away and traveled and again, exposed ourselves to more cultures and different environments.
And then came back and I actually worked at an agency And that was a very intentional decision because I'd never worked as a consultant, basically an agency. And so I worked at an agency at the time called Neon Stingray, where it was small 10, 15 people, but we were building, designing and building projects. apps for in-flight entertainment. So for Qantas, we were doing in-flight entertainment.
We were doing apps on smart TVs. If you remember when smart TVs came out, so we were doing the first set of apps on there. We were starting to do the first video and media streaming apps on Xbox and smart TV and even on the web and on iOS.
uh an android and so that was a very intentional decision a to go and be a consultant go and be at work at an agency see what it's like on that side and then b work with different mediums because you know how to design for a smart tv that's got a remote control that is terrible And the lag is really slow.
And then back in, this is 2010, 2011, like in-flight entertainment where the touchscreen is nothing like an iPad. And also the technology that you used to put in planes, certainly back then it was probably moved on, but the technology was two or three years out of date, but it was certified fit to fly. And that was very important. It had to be certified fit to fly.
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Chapter 6: Why does effectiveness matter more than efficiency in design according to Alastair?
so much of building products today is about collaboration. And that collaboration is human to human connection. And humans are really messy. Like humans are, we're really messy. It's difficult. And then you throw in the, you know, you're right now in Edinburgh, Scotland.
And imagine if we were trying to collaborate together, like, you know, you throw in that we're in a different time zone, that you're at the end of your day, you might be tired. You might be annoyed because you had a long day and I'm at the start of my day in California and I'm like, hey, I'm really peppy. I'm really interested. And you're just like, I can't collaborate right now. Right.
Humans are messy and there's lots of different human behaviors and dynamics that we need to think about. And so whilst I'm not an anti efficiency or anti process type person in general, I understand the importance of these things. I really think you need to stay focused on getting the behaviors right.
in your organization on getting the culture right in your organization getting the right people in you know focus on hiring and quality and then just having this unwavering focus on actual outcomes versus the output you know and i think that is really really important and you know we can talk more about you know some examples of that in a minute
Yeah, I mean, to go back to, and I 100% agree, do you find that as you are identifying what are those key cultural attributes or you're designing like what are the behaviors, does that change from environment to environment?
Or do you find that there's effectively for the teams that I like to run and the business companies that I like to work with, these are the few things that are like the critical things that have really allowed us to become effective?
I think, you know, I've already mentioned some of these things. I think there are some things that stay true and some things that would stay true for me. I have a set of personal values that will always stay true no matter where I kind of work. My personal values are openness. So I'm very transparent. Persistence.
I don't think that anything great happens without a lot of persistence and hard work. I'm passionate. I think people follow passionate people. They want to see that you're excited about something. And then curiosity, right? It's kind of the fourth one is like, you know, you need to be curious, ask questions about the people in the environment that you're in. So I think that stays true for me.
Another thing that stays true, I think for me, and also if I'm thinking about designing and building products is just curiosity. A focus on our core craft as designers. And what do I mean by that? I mean, our core craft as designers is really customer centricity, right? Are we customer centric in what we do? Do we know the problem that we're trying to solve?
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