Effectiveness vs. efficiency in design with Dropbox's Alastair Simpson

Summary

Podcast Summary: Insights Unlocked – "Effectiveness vs. Efficiency in Design with Dropbox's Alastair Simpson"

Release Date: February 17, 2025
Duration: Approximately 50 minutes

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Introduction

In this episode of Insights Unlocked, hosted by Jason Giles and Nathan Isaacs from UserTesting, the spotlight shines on Alistair Simpson, Vice President of Design at Dropbox. Alistair delves into his unconventional journey into the design world, exploring themes such as the balance between effectiveness and efficiency in design, scaling design teams amidst rapid growth, leading in a remote-first environment, and the transformative role of AI in design and research.

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Alistair Simpson's Background and Journey into Design

Alistair opens up about his non-traditional path to design, emphasizing resilience and adaptability. Originally aspiring to be a professional footballer in England, an early career setback at age 16 redirected his trajectory toward academia, where he pursued studies in English, psychology, sports science, business, and marketing. This diverse educational background laid the foundation for his future in design, highlighting the importance of understanding consumer behavior and human psychology.

Notable Quote:
"Design is also about the foundations of our craft... things like being customer-centric, laying out a page, color type, interaction design, and doing critiques really well. That doesn't change."
— Alistair Simpson [04:30]

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Effective vs. Efficient Design

A significant portion of the conversation centers on the distinction between effectiveness and efficiency in design. Alistair cites insights from his colleague Dom Price at Atlassian, advocating for a shift from merely being efficient to prioritizing effectiveness. He argues that while efficiency—focused on process adherence and task completion—is crucial in scenarios like flying a plane, effectiveness—which emphasizes quality outcomes and collaborative human interactions—is paramount in product design and team collaboration.

Notable Quote:
"We need to stop talking about efficiency. We need to talk about being effective."
— Alistair Simpson [21:00]

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Scaling Design Teams in Hyper-Growth Environments

Having navigated through high-growth companies like Reed Business Information, Neon Stingray, Atlassian, and now Dropbox, Alistair shares strategies to maintain design quality and effectiveness during periods of rapid expansion. He underscores the importance of establishing strong cultural values, such as openness, persistence, passion, and curiosity, which remain consistent regardless of the company's size or environment.

Notable Quote:
"I want critique to happen. It needs to be twice a week. But then how you evolve in that is slightly changing."
— Alistair Simpson [26:36]

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Leading in a Remote-First World

Alistair provides an in-depth look at Dropbox's Virtual First model, a remote-friendly approach designed and iterated upon during the pandemic. This model allows for approximately 90% remote work, with 10% in-person gatherings reserved for meaningful cultural and collaborative activities. He highlights the challenges and solutions in maintaining effective critique sessions, fostering trust, and ensuring accountability in a dispersed team.

Notable Quote:
"If you're 20 comments deep on a Slack channel and you see someone typing, that's a sign you need to raise the bandwidth and jump on a video call or talk in person."
— Alistair Simpson [32:49]

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Building Trust and Empathy in Remote Teams

Trust emerges as a critical component in remote team dynamics. Alistair emphasizes the necessity of building personal connections to mitigate misunderstandings that can arise from asynchronous communication. He advocates for intentional practices such as regular customer interactions, transparency through documents like "working with me" guides, and periodic in-person meetups to strengthen team cohesion and empathy.

Notable Quote:
"If we were to never meet in person, a simple question like 'Why did you make that decision?' could be misinterpreted without the foundation of trust and empathy."
— Alistair Simpson [42:53]

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The Role of AI in Design and Research at Dropbox

Alistair discusses the integration of AI into Dropbox’s design and research workflows. He highlights the development of an AI agent that queries existing research, providing summaries and relevant links to streamline information retrieval. This innovation addresses challenges like information overload and context switching, enabling designers to focus on high-value tasks that require human judgment and creativity.

Notable Quote:
"We've created a small agent that you can query, and it will give you a summary and links to specific research. That is a real problem and a real solution that I think AI can genuinely help with."
— Alistair Simpson [48:15]

He also touches upon the skepticism among designers regarding AI's reliability, noting a shift towards acceptance as the utility and effectiveness of AI tools become undeniable.

Notable Quote:
"Six months ago, designers were skeptical about AI summarizing data. Just last month, they saw it as table stakes and expected its integration."
— Alistair Simpson [50:34]

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Conclusions and Key Takeaways

Alistair Simpson's insights provide a comprehensive guide for design leaders navigating the complexities of scaling teams, fostering effective collaboration in remote settings, and leveraging emerging technologies like AI. Key takeaways include:

• Focus on Effectiveness Over Efficiency: Prioritize quality outcomes and human-centric collaboration over rigid process adherence.

• Cultivate Strong Cultural Values: Consistent values like openness, persistence, passion, and curiosity are vital across different environments.

• Adapt Critique Practices: Evolve feedback mechanisms to suit team size and remote dynamics, ensuring continuous iteration and improvement.

• Build Trust and Empathy: Invest in personal connections and intentional practices to strengthen team cohesion in remote-first models.

• Leverage AI Thoughtfully: Integrate AI tools to augment human capabilities, maintaining a balance between automation and the essential human touch in design.

Final Notable Quote:
"Treating our work model like a product, we're constantly iterating, learning, and innovating to make the best work environment for our employees."
— Alistair Simpson [41:35]

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About Alistair Simpson

Alistair Simpson is the Vice President of Design at Dropbox, leading a diverse team across brand, product design, writing, and research. With previous leadership roles at Atlassian and Reed Business Information, Alistair brings a wealth of experience in navigating design challenges in high-growth and evolving environments. He actively contributes to building customer-centric strategies and fostering innovative digital transformations within Dropbox.

For more insights and updates, follow Alistair Simpson on LinkedIn or visit the Dropbox Design blog.

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This summary encapsulates the core discussions and insights shared by Alistair Simpson in the "Effectiveness vs. Efficiency in Design" episode of Insights Unlocked. For a deeper dive into the conversation, listeners are encouraged to tune into the full podcast episode.

Transcript

[Nathan Isaacs]

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 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.

[Jason Giles]

Welcome to Insights Unlocked, an original podcast from User Testing where we bring you candid conversations and stories with the thinkers, doers and builders behind some of the most successful digital products and experiences in the world, from concept to execution.

[Nathan Isaacs]

Welcome to the Insights Unlocked podcast. I'm Nathan Isaacs, Senior Manager for Content production at User Testing. Joining us today as host is Jason Giles, User Testing's Vice President of design. Welcome, Jason.

[Alistair Simpson]

Hello, everyone. Nice to talk to you again there, Nathan.

[Nathan Isaacs]

Yeah, nice to talk to you as well. And our guest today is Alistair Simpson. Alistair 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, Alistair.

[Alistair Simpson]

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 a. 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.

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 our 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, the College of Art and Design in Savannah, talking to students about this who are studying design. I mean, I didn't, I've got a very non linear career path in design. You know, I didn't, I didn't go to a college of art and design and then, you know, take an intern Job in design and then work, work my way up like that. 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, 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. At 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, 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. And when, you know, you have a kind of big disturbance like that where you worked so hard for over a decade for something and then you realize that it's not going to happen.

Like it's especially so earlier in career.

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, I was probably a little bit lost for a while. Right. I, I went to college, which is not American college, like 16 to 18, which is kind of a bit of high school. I studied different things like English, psychology, sports, science, and I initially went to university or college to, to do sport. But then I, after six weeks I, you know, kind of, kind of coming out a little bit of this lostness and I was like, well, if I continue on this path, I'm probably going to become like a sports teacher or something, which no knock on that profession at all. But it just wasn't something I wanted to do. And so I pivoted my university career into basically like human behaviors like consumer behavior and psychology and some business thrown in there and marketing. It was quite a broad degree, but that set me up on the path to becoming a designer because there's a lot of consumer behavior psychology. Why do people do things? Why do, do people buy things? Why do they behave how they want to behave? So that was really, you know, where my I, I'd say that the first inklings of design came from. But, but talking a little bit more, I'll probably talk a little bit more about the football. Like, I think the thing that football instilled in me from being at a professional club until 16 and also then playing semi professional until 37, was just the importance of either what you might call the basics or the foundations of your craft. And in football terms, that's things like being able to pass a ball 10 yards, having the cardiovascular, you know, fitness to run around for 90 minutes, like a very high level. So very small basic things really, like passing a ball 10 yards is not hard. But people often ask me what did I do at practice? And it was like, well, we passed the ball back and forth 10 yards and we did small skills and like, and you're doing that so that it becomes ingrained in you. So that in the pressure situation of a game, you don't need to think about performing a very rudimentary basic skill. And then if you fast forward to what we'll get into in this show, some of my thoughts about design. Design is also about the foundations of our craft. We've got lots of advancements in AI, there's lots of different patterns that come up. But really as a designer, we need to be very good at being customer centric, at knowing how to lay out a page, color type, interaction design and to do critique really well. That, that doesn't change. Like, that just literally doesn't change. And we'll talk about that in a minute. But that's what I learned as a early throughout my football career was just the importance of building good habits, the importance of repetition and persistence because stuff gets really hard. But if you can be consistent over a long period of time and be very intentional, I think you can actually do really great things. And so, you know, I played for many, many years at a very high level of football and I, I was role modeled. Really important lessons. Like I, I was fortunate to have a player manager when I was only 18. He was in his early 40s. He had won the European cup with Liverpool three times in the 80s, which is a huge deal. Like that's a huge, huge deal. And yet there he was, a semi professional club player manager in his early 40s, and he was modeling behaviors. He was first to the dressing room, he would lay the kid out, he was first on the pitch, laying the cones out. He would take part in the drills. So he was involved in it. He would pack away after training. He would clean the dressing room. And this was a guy who'd won the European cup three times. And I'm like, wow, he is modeling all of these behaviors as a leader. He is involved, he's engaged. And so I learned a lot from that, from football that I've taken into building teams. And then the second important lesson or work experience that is not designed, I went traveling around the world. 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. Where I was living, and I got turned down by all those graduate jobs. So, you know, 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 I saved up money for six months. I worked at JP Morgan Chase bank doing some data entry and 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, you know, listening, asking questions, and communicating.

And at the time, did you. Did you recognize that you were gaining these kind of core foundational skills, or was this something that you were just like, hey, I'm on my. I'm on a journey and I'm, you know, just. Just moving through, happy, go, lucky. Trying to figure out what's next, I'd.

Love to say, because certainly as I've got older, I'm very much more. I am very intentional, like, really intentional about the things that I do and how I learn and what I'm exposing myself to so that I can really develop myself in an intentional way. But honestly, the candid answer is no. The only thing I will say is I was very intentional about, okay, I've had this setback where I got turned down from jobs. I'm going to go and do something very different 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, looking back at that time, because I do reflect most years now 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, 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, that 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 at a B2B publisher called Read Business Information, which is part of the LexisNexis group or Reed 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, your GQ or something, right? They weren't these consumer magazines, obviously. In the early 2000s though, print publishing was declining rapidly and revenue is 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, 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 more software. Oh, more, more.

[Jason Giles]

That's right.

[Alistair Simpson]

Takes me back.

It's right. And I remember buying it and it was felt like offensively expensive at the time. It was a few thousand dollars or something. And, and so I was doing all this, all this very broad design work, building prototypes, like doing wireframe, all the things. And honestly I probably was making so many mistakes, but I was just doing the work. I was just doing the work. And I got a lot of mentors because I was a design team of one. I didn't have like a manager or director. It was literally just me in this small 10 person company and. But I got outside help. I got lots of mentorship from different people. Like they taught me how to do good research, they taught me how to do good visual design and branding and the importance of page hierarchy and all these fundamentals. And then I went and learned and studied myself. And so that was my introduction into design. But that was a huge, again I look back on that, the intentional decision there was to work for them because they were in Australia. But it was. So I was Very fortunate because.

Little bit of luck there.

Little bit of luck, yeah. Because honestly, it was like a startup and this was in the early 2000s, as I said, we went from 10 to like 150 people in two years. I was like, wow, this is crazy. But it's only now when I look back and I've worked in Silicon Valley and I've seen tech and startups that I'm like, oh, wow. Like we were doing a lot of the things that are happening now in these crazy, you know, fast growing startups back then and just trying to make it work, essentially.

Totally, yeah. Quick sidebar. I was, my first job, my entry into design was working for the Microsoft Library, which at the time was the world's biggest intranet. And one of my jobs was to log on to LexisNexis, get all the files down and format them in HTML and so I can publish them to the rest of the company.

So I mean, that's, that's the thing, because you forget that back in those days that, that was what it was. You used to have to go to the LexisNexis, like directory, right, to download the information. Like that was how you got your information. It's changed so much.

Oh, 100%. So you was, it was a read. Was. That was the name of the.

Yeah, it's RBI read. Business information. That's where I initially started and.

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 pursue?

Yeah, these were definitely more intentional. I mean, I. In between those, 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 apps for inflight 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 and 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 plane, certainly back then it has 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. And so you're already working with technology that was two or three years old. But it was very interesting time because you learn to design with a lot of constraints and really understand the technical aspects of what you're designing with. And so I did that. I loved it. I had a great time and then went to Atlassian. And again, Atlassian was a very intentional move because I wanted to move back client side. I'd enjoyed my time at agency, but I wanted to go back client side. And Atlassian in Australia was, you know, the, it was pre IPO, it was about 900 people, so it was relatively small to what it is today. I think they're at 15,000 people today. And the design team was only 20 people. And I was roughly like designer number 20, approximately. And I remember talking to Jurgen, who was my boss for the whole six years that I was there. And he said we were talking about why I should join and he was like, Atlassian is very much an engineering led company at the time and that we're really trying to become an experience led company. And that was a really big challenge. And that really got me excited for that particular challenge as well. As Atlassian was a very mission and values led company, which is similar to Dropbox. Dropbox is a very mission and values led company. And that's something that I've learned is very important to me as a person to make sure that you're working for a company that you're aligned to their mission and values. And so yeah, they were certainly intentional decisions to move there.

Amazing. I mean both, I mean between Reed Atlassian and now Dropbox, all very. You've been through three rounds of extreme high growth. For me, it starts begging the question, like either what strategies did you use or what strategies did you learn in order to Kind of maintain whether it's efficiency or efficiency and quality during all those changes.

Yeah, I mean this is something like a good friend of mine, Dom Price, who influenced me a lot. He's at Atlassian, he's still there. And he was my buddy when I joined, but he early on influenced me where he was like, we need to stop talking about efficiency. And I was like, what do you mean? He's like, we need to talk about being effective. I'm like, I'm like, okay. And then when you start teasing that out, I think that's actually very, very true. And I'll start with where may you want to be efficient or have like a task list based approach to something, Flying a plane. Very important to have like a task list efficient approach to scaling that safety procedure. I think that where we're talking about building products and working, you know, in building products in technology, I think we often get stuck trying to mandate process or efficiency and then measuring adherence to the process versus and you alluded this to, versus the actual quality of what is being delivered. And that's really what's important. And I think that's bad. And I think 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're right now in Edinburgh, Scotland and imagine if we were trying to collaborate together. 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 know, 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, some things that would stay true for me. I have a set of personal values that will always stay true no matter where I, 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, is 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 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? Do we actually know the problem and what a good outcome might be? Do we know how to go broad with solution generation? Like do we actually, instead of just designing one idea and calling it quits, do we actually know how to do good solution generation? And then do we have a strong foundation in type, color, page hierarchy, interaction design and then lastly how you give and receive feedback. So is your critique happening once, twice per week? Is it a real debate led culture where you're evolving an idea? Those things I think stay true for me no matter the environment that I'm in. I think they're consistently the way that you can get to innovative outcomes. The things that may change though are the small nuances around the culture that you're working in. Because every company culture is slightly different. You know, Atlassian had a company value of open by default, basically. So everything in Confluence is opened by default. Which many people come into the organization more like, whoa, like I make a page and everyone can see it. And it's like, yeah. Whereas if you go work, I've got, you know, Apple is a good example, right? It's very much a Different culture, where it's closed by default. Right. And there's nothing right or wrong about either of those cultures. I don't think they're just different and they're the things that can change. Because I think both companies in those example, Atlassian and Apple, can obviously produce great outcomes with those different cultural values that they have. It's just that they're just a different environment to work in. And then you as a person need to adapt and stay true to your own principles, but then adapt to the local environment that you're in to make sure that you can build things that matter.

Yeah. So let's take an example. One of the things that you mentioned that's pretty consistent across environments is critique. So in a fast growing company, that's something that I would imagine, frankly I've experienced of having to scale that and do that maybe. Do you have an example? I know you've spoke a lot around Virtual first environments and having to think about the ways that we work, but is there a kind of an example of how something started, you know, worked well and held true at a certain size and then after this dramatic scale, you had to think about different ways to still accomplish that?

Yeah, of course. I mean, I won't talk about Virtual first yet, but I think Virtual first is a good example of some of this that I'll talk about in a moment. And Virtual first is the Dropbox remote model that I helped design for those listening in. But let's go with critique. Right. When you're in a hyper scale scaling environment or actually, let's just take it right back. When I was at an agency, we had five designers so we could do critique in person twice a week at a wall because we were all in the same location. Great, that was awesome. And I'm sure everyone that's listening wishes that their day was exactly like that because. But what happens? And then, you know, I moved to Atlassian and I had a team in Sydney and initially I had a team in Vietnam. Atlassian had a Vietnam office for a little while. Right. And so my principle of like critique was like, right, we're going to do critique. It's going to be once a week. It's going to. And then me as a leader, I'm like, oh, okay, so some people are in an office in Sydney, some people are in Vietnam. The time zone is different and we can't all see each other. It's really hard to look at the work. And okay, so what we evolved. It didn't really work for a while. Right now I didn't throw out my principle that I wanted to do critique once a week, but it's like, how do you actually scale that now your team is 20. All 20 designers have to be there. Or is it critique at a smaller level with five designers? And then how do you use the mediums in more effective ways? This is one of the things I started to learn at last year and really evolved at Dropbox as we've gone all in on remote. But how do you actually use asynchronous methods of giving critique? How do you actually use more synchronous methods when it's more critical? And so that is an example of how that critique evolved, where we started to do live critique. So it's synchronous, but we gave asynchronous feedback in a document, and that document had different levels of feedback. So I think Liam came up with some of these, was like, okay, this is a torpedo. So this is like, really important feedback that I need to give you versus this is just a niche. This is a nit piece of feedback. I don't know. But we would give this and we would do this asynchronously because it just didn't. It wasn't like you're at a wall together. Like, you could actually, like, see and feel it and just have a debate. But then after about 10 minutes of asynchronous feedback, we would come back and discuss live. But obviously we would talk about the torpedoes first because they're the most important things to talk about. Right. And so you start to evolve your practice, and I think that's what you have to do. As you scale, as your team continues to grow, you need to have some principles about how you work. I talked about some of mine, like openness and persistence, like the belief in critique. But you have to evolve how that process happens. We can't all just wish that we were five people standing at a wall in the same room at the same time. Like, it just doesn't work like that. And so how you evolve your practices to where I'm at today at Dropbox, Dropbox, the team is roughly 100 ish. A bit over 100 people in design. Critique happens Tuesday and Thursdays, so twice a week. I'm a big believer in this now, where you present an idea on Tuesday, you get feedback, and then by Thursday, you've done some iteration on that feedback. Because, you know, too often I think feedback goes into a void and we don't know what happens with it, but that forces you into that loop. So Tuesday, Thursday. Now, that doesn't mean that we've got 100 designers all in one room, like, doing that. The teams are organized into smaller units and they're doing that critique. And different teams have a little bit of latitude about how they're doing their critique. Like, different design directors will be running their critique slightly differently. However it's happening, the feedback is getting logged, it's getting actioned, and then they're coming back and they're doing it the following week. Because I have a belief that you need to debate the ideas very frequently, like once or twice per week in order to build on those ideas. But how the critique is happening is slightly changing. And there's some latitude to the.

This is going back to kind of your principle about being very outcome focused. Right. Like what you want the outcome to be is that the fact that this activity or this kind of thinking has happened.

That's right.

How it gets done, either there's latitude across your different directors or it has to change over time as circumstances change. We all learned this over the pandemic of, like, look, we still need to have the same, oh, now we got to apply our creative skills into how we get done.

And I like, you know, again, I learned this well. I like thinking about practices, not process. That's kind of what I, how I define a practice is it's got guardrails and it's more of a framework, but within that you can move around a little bit versus a process is very like, did you do these six tasks? Because. And I'm more interested in the practice. And my practice is like, I want critique to happen. It needs to be twice a week. But then how you evolve in that is, you know, there's a little bit of latitude.

It's interesting. We, you know, we, we look at some of these agile processes on the engineering organization. There's this thing like the definition of done.

Yeah.

Like, there's the checklist. And that doesn't necessarily mean it's this checklist of all these activities. It's, did the outcome happen? And thinking from that perspective of like, yes, did this get. Is this accessible? You know, like, it. How you got it to there. There's.

There's lots of different ways and, and that's totally true. And this is the other thing about outcome focused. It's also about giving designers all the way down the accountability that they own something, that they are the owners. Like, just as you said about accessibility, like, have you got accessibility baked in from the start? Like, you own that. Like, you don't Own the Figma file and then hand the Figma file off. You own the outcome of it shipping to production and it being accessible and how you wanted it to work and that it and you own that jointly with product and engineering. And you need to feel that accountability. And I think again, we've all lost a little bit of that where we don't feel the accountability so much. And I want people to feel that accountability because I think that's a good thing. I think it's actually a really great thing that you own something and you.

Talk, you talk to designers, researcher, writers, like any creative. Like that's most employees in general, they want, they talk about autonomy, they want about feeling a sense of control. Well, that's that, you know, here's the outcome and figure it out. But then also you are accountable for it. Like there's a sense of pride and ownership around that.

Yeah, totally. And then, you know, I mean, this is obviously for me, but going back to how I've thought about this, it's like I think that people do want that accountability and that autonomy, but then often we get caught up in like the new shiny and trying to reinvent the wheel when really like, you have a lot of latitude and as a designer you have many tools in your toolbox, but the fundamentals, the foundations of like good interaction design, you know, page hierarchy, like understanding the problem, like being custom, that doesn't change. And you don't need to actually innovate there. You actually don't need to innovate there.

Yeah, no, totally, I agree. So it wouldn't be a user testing podcast if we didn't talk and get your perspective on how you are cultivating customer empathy. Especially, you know, you've worked in so many different environments. I, my guess is your travel experiences as well have also kind of fed into that. So I'd just love you to tell us a little bit around kind of your approach to that.

Yeah, I mean it starts with the personal values I've already talked about. So openness, right. I'm very transparent. I have a readme document or a working with me document that's like five pages. And it's not just like how do you contact me? It's like, here's my background, I went traveling. This is where I grew up. Here's some photos of me growing up. Like, it's pretty in depth, but it starts there about. And also in that document it's got. These are the things I believe in because I believe in certain things, like craft being incredibly important, about building teams like how I think about building teams, not individuals. Right? And so this document's got a lot in there, but that starts with sharing. And hopefully people are getting empathy for how I think and how I want to engage with an organization. So it starts there and in there it's got my personal values around openness, passion, persistence and curiosity. And I think I model that day to day. And honestly, I think those, the reason I have those personal values is I think that if I'm open and transparent, if I'm persistent and if I show up and I do the work and I do the things that I'm supposed to do on time, if I'm passionate and if I'm curious and ask questions and I'm trying to uncover, you know, what is important for other people, that that will build trust and that will build empathy and that will start to seep into everything that my team does. And so I, I think that that is genuine, genuinely true in how I think. I, I also, because obviously, you know, I mean, use the testing. I mean, you also need to not only build empathy for the people you're working with, but obviously for your customers and then modeling that behavior. I try to speak to customers every week or at least every two weeks. We have various different customer connection programs, customer coffee chats. We can watch usability testing sessions, we can speak one on one to customers through our sales. I can follow, I follow some customer support, like live chat messages with agents. So there's various different ways. And if you start modeling that behavior, that customer centricity is important, then again that your team is going to get an understanding that that is really important as we think about empathy and building that empathy. I also, it's a good opportunity and probably relevant. You mentioned the pandemic, but to talk about remote versus in person, right? I think.

Right, yeah.

Because again, as I thought about how do you build empathy with your team like at Dropbox, for context, I helped design our remote model. So when the pandemic happened, as destructive as it was and awful, Dropbox saw that as an opportunity to rethink how work gets done. The Dropbox mission, which I was very much pulled towards when I joined Dropbox, is to design an enlightened way of working. And so we really leaned in during the pandemic to really design a better way of working for Dropbox employees. We saw that as an opportunity. And so for two years I co led our shift to remote work and I was essentially applying human centered design to the employee experience. So talk about building empathy. We had a Researcher following employees as they went through the ups and downs of trying to transition to remote work. And we learned a lot of, we got a lot of empathy from people about the things that worked, the things they loved and the things that they hated and that were not going well. And we've ended up with a model called Virtual First. And we're about, we're approximately say 90% remote, where we're majority remote, but about 10% in person. But importantly, that 10% in person is very intentional and meaning for meaningful moments of culture building or collaboration. So we don't come together just because it's Tuesday or Wednesday. It's because we have something specific that we want to go through and we need to be in person to do that. And so that could be like an end of quarter retro, a start of quarter kickoff, a leadership off site. But it's a very intentional moment. And it's also a key part of gathering in person because that helps build connection and empathy. Right. Like, and because it's very different when you're breaking bread with someone, having coffee with someone, versus being on Zoom or how we are now, like there, the different mediums are good for different things. And obviously meeting in. There's no substitute, I don't think, for meeting in person, say once per quarter and actually breaking bread and understanding that who that person is.

Yeah, well, we were traveling more. We, we were, we're quite distributed and we've always been very remote friendly. But it's funny because we, we merged with user Zoom.

That's right.

And bring, bring two companies together. And so right from the get go, like, let's get in person. And what I noticed, like, basically you'd build these connections. And I think of it like putting oil in an engine. You could start telling, like when friction starts building up, you're like, things get heated, misunderstanding sound like, oh, it's time to add a little bit more oil. So I totally, I love what you're saying about that intentionality. And then the, the other thing that I really appreciate is you're just such a designer. Right. Like, how do we solve this problem? Oh, let's just apply design thinking the way that we solve problems.

And that's totally. I mean, I want to talk a little bit about trust, but just on the Dropbox thing, it was about, okay, how do we challenge assumptions, which is great design. Right. And it was like the eight hour workday. Why is it a linear eight hour workday? And actually it's really like a 10, 11 hour workday. Because I get messages on my phone now and I reply when I'm not in the office, quote unquote, right? And when you look at that, why it's an eight hour linear workday, it's because of factory work. Like we start the people punched in at nine and they finished at five and there was a break at lunch. And the modern office pre pandemic hadn't really changed. Like it honestly hadn't changed. We still went to the same place, synchronized in time. Even though we had colleagues all over the world, we still went to an office. And so how do you challenge that assumption of an eight hour workday? And so that's what we did at Dropbox where we came up with a model of core collaboration hours, which is four hours of synchronous time per day. So for me on the west coast that's nine through one where I'm expected to be online for synchronous collaboration. That means meetings, replying to Slack in time. But outside of that we encourage people to do their own non linear work days where they work. You know, we haven't shortened the workday from eight to four hours. We've just said hey, if you need to go be a caregiver between one and three, that's cool. But like so long as you're getting going back to outcomes versus outputs, so long as you are getting the outcomes done, that is more important to us than this kind of butts in seat mentality and making sure you're online at specifically 1:05pm and the outcomes for us have been transformative. Right? We've been.

Yeah, I was going to ask, so what has the outcome been for Dropbox?

The outcome for Dropbox has been transformative. We can hire all over the US like we've been able to tap into talent, we've never been able to tap into pre pandemic because we had to have people in the office. We it is virtual. First is one of the number one reasons that employees join Dropbox and the number one reason that people retain and stay at Dropbox. Our self reported productivity scores the highest they've ever been ever. And people feel like they can do the best work of their lives at Dropbox. In the model that we have and treating it like a product though we haven't, we're not setting and forgetting, we're actually continuing to iterate. We've got a new concept called anchor weeks where we're trying to bring people together like an entire squat, like an entire team together for a week of intensive. And so we're constantly Iterating, it's just like a product. We're learning, we're listening to employees, we're learning, looking at the data and continuing to innovate. And I think that is, as you said, it's a good use of design in a different realm than building products, but using the design thinking toolkit or the designer's toolkit to kind of rethink and challenge those assumptions.

Well, and it's so awesome that you're in a position there where you can really lead some of those efforts with that kind of empathy. First perspective.

Yeah.

You mentioned trust and its role within building empathy. How does that play into all that?

Well, I think I wanted to give this example I've used down the years about trust. Right. If you think about it, and I used to have teams in Sydney, Australia and the West Coast, US So different immediately. Different cultures, different time zones. And if you think if, if I'd never met you, let's imagine I was in Sydney and you were in the US and we were talking on. Name your tool of choice, like Trello, Jira, confluence, anything like Git, whatever you're using. Right. And you wake up to a comment that I've made in Australia the day before because of the time difference. And the first comment you see is, I've said, hey, what? And let's actually. Let me set a bit more context. We've never met. Let's imagine we've never met in person. Maybe we've been on some zoom calls and I left a comment on this thing that you're working on that says, Jason, why did you make that decision now when you read that? Because you're not hearing that. When you read that, what you're reading is, you're a fool. I don't trust what you're doing. Why did you make such a stupid decision? That's what you're reading. Even though I just said, why did you make that decision? There's no challenge in it, but because across the time zone, across the world, you're in. You're waking up. It's the first thing you see is the end of my day. The context is lost. And also there's no trust or empathy between us. We've never met. Versus imagine if we'd met, we'd had coffee together, we understood who each other were, we knew each other's kids or whatever it was like whatever the personal settings are, we'd actually met. And then I asked that question, that same question. Why did you make that decision? You're immediately going to have a different Perspective and read that question very differently. This is where my human psychology background comes in from university is it's like that is just psychology. But that's how you build. That's why it's important to meet in person and build that trust. Spend the time building trust. And even one of my personal values of curiosity, when I start working with new people, I ask questions, who are they? What is going on for them? Like in work, outside of work, like be curious, ask questions, build up your own set of information so that you have more context of what somebody's going through. So that's the trust thing I think is very important. And then just rounding that out. Whilst I am a firm believer in remote work and asynchronous work, by default you have to know when to move that synchronous. Right. If you're 20 comments deep on a Slack channel or you can see in Slack where you can see Jason is typing, Nathan is typing, Alistair is typing. It's like that's a good sign that you need to raise the bandwidth and jump on a video call or like talk. Talk like not chat or meet in person because probably the problem is bit bigger than that. And so, but. But we miss these social cues. I think we often miss these social cues and we rely too much on the tool. You know, we hide behind it a little bit.

No, I see that 100%. And when I was talking about the engine getting friction, most often it's when I see misunderstandings that often are from those asynchronous. Because that foundation there, you're like, oh, wait a minute, these guys have forgotten that Susie's sense of humor is this way or you know, like it takes time to build. And as it's been a real challenge with trying to establish. I worry sometimes about the kind of remote first and remote only next generation and how they're developing those skills and their speed and maybe some. Either we'll have a conversation or maybe we'll have you back on the show and kind of talk about like the, the future generation of designers and, and some of the opportunities there. There's so much going on. I could probably. We could just go on and on. I could talk to you about so many subjects. I've really enjoyed our conversation. Was there anything specifically that you wanted to call it? I know, you know, we were talking about the efficacy of design, how to scale it, but was there anything specifically like, you know what, I have to make sure that I call this out.

No, I think the. I mean, I don't know whether it would be a podcast if we didn't talk about AI in design nowadays.

Yeah, yeah, that's fair. I mean, how is your team utilizing it? Are you super powering yourself?

Look, I think, I mean, Dropbox in general, we've Long believed in AI's potential to transform knowledge work in general. And I think the recent advancements are just unlocking a lot of new possibilities to solve some of the biggest challenges that we all face today. Things like information overload, context switching, lots of browser tabs. There's a lot of opportunity for AI, I think specifically for design though. One of the best early use cases that I've seen leveraging AI has been which solves a real problem, which is, it is research related. And I'll talk a little about our own solution is like we created an AI agent so that we could query the existing research that we have. So you can actually go and query it to see what we've got. Because if you think about it prior to that, it's like, okay, where was the folder or the file or where was the page on our wiki or whatever? Where was it? Who's got the knowledge of that? I'll ping Jason and I'll ask Jason, because Jason will know about it. He did the. Oh, that person's left. And okay, that's a real problem. That is a real problem. And so we've, you know, we've created a. Just a small agent that you can query it and it will give you a summary and then links to specific research about. Okay, you're doing onboarding. Who's. What do we know about onboarding for Dropbox customers in the past? And I think that's a real problem and a real use case. And you know, and then summarizing existing research, because if you think about it, if you're doing deep ethnographic research or you've got a dozen videos, like how do you actually summarize that content very quickly? And that's again something that AI can do. And I know user testing has different platforms to be able to be able to do that. That is a real problem and a real solution that I think AI can genuinely help with.

Yeah, it really is. And what's really interesting, so clearly, you know, we're really investing in all of those scenarios you can actually just talked about around productizing that. But the thing that fascinates me, you know, I, I've got a gray beard. I've been around for a long time. I was there when the Internet came.

Yeah.

And then I was there when mobile came and. And this is very similar of that. And however, what is remarkably different is.

The speed, of course.

And when we. At the speed of change and when we talk to our primary core customers, which primary designers, researchers who are naturally skeptical. Six months ago, you know, we talked about summarizing data and stuff, they're like, forget it, I don't trust machines and like, I need to like do it myself. Literally just last month we did another just pulse check and well, they're like table stakes. Of course we expect it. And so one, I'm thrilled that the utility and the power is being able to enable these teams and I'm thrilled that we're actually being able to embrace it and apply it in a way that's going to make us more effective.

Yeah, that's right. I mean, and even with that though, there's. Because as well, I think in pure design you've got AI can definitely help with things like solution generation, give me different solutions for this specific problem. And even in the examples we've talked about, getting summaries is important, but you still need someone with judgment and taste in that loop to actually pare down and really understand it. It's just as you said, that task that is actually quite laborious of actually going through and really synthesizing can be done quicker for you. But then it still takes a human. Talk of the human in the loop. But I think it' in design, it's someone with judgment and taste that can actually like decipher and like make a path forward. I don't think that's going to go away.

I'm 100% agree. Alistair, thank you for coming on the show. This has been like so great. It's so great to meet you and it's been really lovely. If folks want to learn more about you, see what you're up to, where's the best place that you would direct them?

Best place? I mean, for me personally, it's LinkedIn. I don't really use X or Instagram or anything else, so LinkedIn, you'll find me there. To search for my name For Dropbox, you can [e-mail] for our design team blog and then Dropbox Design on Instagram. I think there'll be a lot more happening on those in the coming months, so that's where you can find us.

Brilliant.

Thank you for having me on, Jason. I appreciate it.

Absolutely. The best to you, the best to the team at Dropbox. And here's to more future success.

Thank you.

[Jason Giles]

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