Alastair Simpson
Designing Your Way Up Mt. Business
In this episode of Brave UX, Alastair Simpson shares how rejection fuels progress 🔥, the role design has played in transforming Dropbox’s work culture 💡, and how to build effective executive-level influence 👂.
Highlights include:
- What is the beauty of rejection?
- Why don’t you like the phrase “getting a seat at the table”?
- Why have you designed your VP of design role so broadly?
- How have you supported people to find their feet with virtual-first?
- Why do you find business conversations intriguing and empowering?
Who is Alastair Simpson?
Alastair is the VP of Design at Dropbox, the one place to keep life organised and keep work moving 🛹. And it’s been keeping a lot of people doing just that, with over 700 million users, across 180 countries, and eight productivity-enhancing apps.
At Dropbox, Alastair leads a talented and diverse team that spans across brand, product design, writing, research, and operations. He is also working with other company leaders to apply human-centred design internally, designing the future of work for Dropbox’s employees 👩🏾💻.
Before joining Dropbox, Alastair was a Head of Design at Atlassian, where he helped to scale the design team from 20 people in 2014 to over 300 people in 2020 📈. During his time, Alastair led the design of a number of products, including Trello, Jira, and Confluence.
As someone who believes that design leaders are business leaders, Alastair has generously shared the learnings from his ascent up Mount Business 🧗♂️, speaking to fellow designers at events such as the DesignOps Summit, Bureau of Digital, and the Leading Design Conference.
Transcript
- Brendan Jarvis:
- Hello and welcome to another episode of Brave UX. I'm Brendan Jarvis, managing founder of The Space InBetween, the behavior-based UX research partner for enterprise leaders who need an independent perspective to align hearts and minds, and also the home of New Zealand's first and only human-centered research and innovation lab. You can find out a little bit more about that at thespaceinbetween.co.nz.
- Here on Brave UX though, it's my job to help you to keep on top of the latest thinking and important issues affecting the fields of UX research, product management, and design. I do that by unpacking the stories, learnings, and expert advice of a diverse range of world-class leaders in those fields.
- My guest today is Alastair Simpson. Alastair is the VP of design at Dropbox, the one place to keep life organized and keep work moving, and it's been keeping a lot of people doing just that with over 700 million users across 180 countries and eight productivity enhancing apps.
- At Dropbox, Alastair leads a talented and diverse team that spans across brand, product design, writing, research, and operations. He's also working with other company leaders to apply human-centered design internally designing the future of work for Dropbox's employees.
- Before joining Dropbox, Alastair was a head of design at Atlassian where he helped to scale the design team from 20 people in 2014 to over 300 people in 2020. During his time, Alastair led the design of a number of products including Trello, JIRA, and Confluence
- And what must feel like another life by now, Alastair worked at an agency called Neon Stingray, now called Valtech as the head of user experience where he managed a team that designed apps for use across web, mobile, inflight, smart TVs, gaming consoles, and tablets.
- As someone who believes that design leaders are business leaders, Alastair has generously shared the learnings from his ascent up Mount Business, speaking to designers on both real and virtual stages, including those of the Design Ops Summit, Bureau of Digital, and the Leading Design conference.
- He's also been recently interviewed by the Wall Street Journal and Fortune, and now he's about to have a conversation with me on Brave UX. Alastair, hello and a very warm welcome to the show.
- Alastair Simpson:
- Good afternoon, and thank you for that lovely warm introduction and hello to everyone listening wherever you are in the world or whatever time it is of day.
- Brendan Jarvis:
- Yeah, so well hard to know for us, isn't it? But it's my morning, your afternoon, and we are here now. And I want to start with something that I discovered about you. It's actually, it's a bit of a rumor, it's a public rumor and that's that you own apparently a rather large sneaker collection. Is that true?
- Alastair Simpson:
- That is true. That is very true. I have consolidated a little bit onto three styles of sneaker and three, any sneakerhead listening? I'll start with the least interesting one. So Vans authentic, I have a number of different colorways than those Edge Jordan one. I have lots of those and Nike Blazers. So I, I've consolidated to three. The wider story on that is though it's part of a uniform that I wear generally, sneakers, jeans, and a different t-shirt. I generally only wear t-shirts you made never see me in a shirt. So yeah, it's part of a uniform to reduce the number of decisions they have to make every day. So yeah, that is a true rumor.
- Brendan Jarvis:
- Have you come across Kevin Bethune in your travels around West Coast design and tech?
- Alastair Simpson:
- No, I haven't. Haven't actually.
- Brendan Jarvis:
- Kevin's, yeah, so Kevin's a previous guest of the show. He runs a design strategy consultancy called Dreams Design and Life, and he used to be a footwear designer at Nike as part of many other amazing things, including being an engineer and a new and a nuclear power plant. So Kevin's had a wonderful career and I should definitely connect the two of you. I was curious though, what is it about sneakers for you? Why collect things like collecting things as a hobby? What is it about sneakers that you find gratifying or interesting or enjoyable?
- Alastair Simpson:
- Well, I some of the different, it's super interesting you're asking a bit about my sneaker sneaker collection. By the way, Brendan and I appreciate it deeply as a designer because that's somewhere in why I like sneakers. I'm looking down at a book because one of the books I have on my desk is called CoLab, which is sneakers Cross culture. And if you're not into that many don't know the background in sneakers, you have the generic types of sneakers. And then you started getting collaborations with different artists who would put their own unique design onto sneakers, and that allows people to express a little bit of who they are and shares a little bit about, for me, it's an important aspect of how I think about my uniform or how I come across or how I present. And then also is this at the different types of identity you can have in these collaborations.
- My favorite sneakers are a collaboration between Nike and Slam Jam, which is kind of a snake skateboard kind of brand, and they actually invert the Nike Swoosh on the side of these standard blazers. So they're just a basketball shoe from the seventies that have the upside down Nike Swoosh. And I just think that's really cool and slightly different and it just allows you to share a little bit of your own personality in something that you're wearing, but also shows that you care about your appearance and how you come across. Which again, I think it is an important facet of design
- Brendan Jarvis:
- That would've been a controversial decision to get past the he head of design or the VP of Design or chief design officer at Nike.
- Alastair Simpson:
- Interestingly, I presented to the Dropbox board a number of times last year, and the chair of our board used to be the CFO F O at Nike for about 10, 15 years. And Don shared me, he was like, controversial decision are they're IP lawyers. Were questioning some of those decisions, but because it is, it's part of their brand, right? It's a very integral part of their brand that these collaborations are changing, which is be somewhat controversial.
- Brendan Jarvis:
- If anyone's ever seen a brand guideline who's listening to this, you'll know that there's always a couple of pages in there of the dos and don'ts with logos. And one of them is don't change the orientation of the logo.
- Alastair Simpson:
- That's right. But I just find it interesting and fascinating and I think it brings more personality to some of these collaborations and some of the sneakers that I buy 'em wear
- Brendan Jarvis:
- Possibly not a sneaker collaboration or probably doesn't fit that box, but there's a company based in the US but founded by Kiwis, as far as I know, called All Birds and Oh yeah, yeah, you've heard of All Birds. So if you want some footwear that's sort of a bit different to your regular sneakers, just for a bit of comfort, then All Birds, I highly recommend them. I'm wearing a pair of them right now.
- Alastair Simpson:
- All right, nice. Yeah, I don't own all birds, but I do know, I do know what,
- Brendan Jarvis:
- Now you mentioned earlier when we first started talking that your uniform doesn't include shirts, but I've seen a photo, I've seen a photo of you in the early two thousands hard at work at a whiteboard with a bunch of Post-it notes and you are sporting, apart from wearing a shirt, you are also sporting a haircut that's reminiscent of No Gallagher from Oasis. Were you a bit of an Oasis fan when you were growing up?
- Alastair Simpson:
- Oh, you have done your homework. That photo was in a book with Donna Spencer who I know that you've, you've had on the show and she asked me if she could use it. I was Affinity Diagramming, right? I was a UX team of one and I was Affinity Diagramming and so interesting. That would've been 2005, maybe, something like that. And back then I think my perceptions changed a little bit, but I was wearing a shirt and I was wearing shoes, like proper shoes and tailored pants and I think it, I showed how the culture has changed in the world of work. But yeah, I definitely was wearing a show. I was an Oasis fan and still am an Oasis fan. I generally listened to lots of different genres of music. Now I don't actually listen to Oasis that much, but back in the day I definitely was, my hair was probably inspired by Liam Moreno, one of them for sure.
- Brendan Jarvis:
- Well, speaking of Liam Moreno, given what happened with Oasis, and for those of you who dunno what we're talking about, we're talking about the greatest rock band in all of the world's history, a Brit pop band from the nineties and their two brothers, Noel and Liam, and they split the band split and they're no longer a band. Are you in Camp Noel or are you in Camp Liam?
- Alastair Simpson:
- That's such a hard question. It's like choosing your favorite kid. I'm Camp Liam. I would guess maybe there's no real why to that I haven't followed the spats that have been sued since their glory days. So I don't know, but I'm probably a Camp Liam, I would say.
- Brendan Jarvis:
- And before we move off this topic, is there any chance that we might see a return of the Oasis inspired haircut?
- Alastair Simpson:
- No, that is a former hair, hair phase should we say. I'm just thankful that I still have all my hair that's genuinely, I'm going gray. I dunno if that will show up, but I'm definitely going gray, but I'm just thankful that I have all of my head of hair. But no, probably no more oasis.
- Brendan Jarvis:
- Okay, good to know. Good to know. All right, well let's come to your path to design now. Now I went back and had a look at your history and who'd you talk about this as well? And you didn't train as a designer, did you?
- Alastair Simpson:
- No, I didn't. That's right, that's right. I mean the backstory that you won't have even seen on LinkedIn, because I guess you don't put this on LinkedIn, is I actually wanted to be a professional soccer player or football for being from England. And I was actually at professional club until the age of 16 and I didn't make it at the age of 16. For those who aren't aware of 16 is when you either get taken on a professional contract or not and I didn't make it. And at 16 I was honestly very sad about that. I did continue to play semi-professional football until I was 37 when I always do the air quotes when I had to retire. It makes me sound nicer, it makes it sound better I think. But I did play semi-professional or 37, but outside of the football, no, I didn't start in design.
- I mean the full story, I was applying for graduate jobs in London and I got turned down by, I think it was three or four different graduate jobs. And my best friend at the time said, Hey, do you want to go traveling around the world? And I was like, well, that sounds like something I would've normally said no to. Having never really left England. And lo, next thing I know I saved off a bunch of money and I went traveling, started in South America. First stop was Rio in Brazil and then we traveled all around South Central America, New Zealand. We came to your hometown in Auckland and went to the north and South Islands Australia, Southeast Asia. And then after a year of traveling, I remember calling my parents, this is back when you had to get phone cards, there wasn't mobile phones. This is 2003, call my parents, I'm like, Hey, I'm not coming home.
- I'm going to go back to Australia and live and work for a year. And I went back to Australia, didn't have much money at all, honestly, had a few hundred pounds in my bank account at the time and there was only a few different types of jobs you could get as on a short term working visa. And I ended up in a call center, that was where I ended up doing inbound and outbound sales essentially. That was my first inverter as real job outside of college. But something that, maybe we'll talk a bit more about this, I learned a lot about the power of communication, the power and the power also of listening like active listening and asking questions. Because really while sales and call centers can get a bad rap, that's really what you have to do in those scenarios. You've got someone on the phone who's angry with you, how do you listen, ask questions and actually communicate effectively and clearly with them.
- But that was where I started. Then I went back to London cause my visa ran out and I started working in a kind of marketing s e o kind of role. And then eventually found my way back to Australia where I was working at the time, the largest B2B public publisher in the world. Reid business information there, you've never heard of them. They had magazines, like print magazines and things like agriculture, farming, architecture, manufacturing. But in Australia, I was working for the digital division, which was just 10 people. And we were taking a lot of the print revenue, which was obviously plummeting at the time in the early two thousands and transferring it online. And that was where I became a designer. My, the C E O took a chance on me essentially, and he transitioned me into this kind of hybrid design product manager role.
- And I became a design team of Oneg. I was doing interaction design, visual design, branding. I built my own usability testing lab using Moray software for anyone that remembers Moray. It was like $2,000. It was a huge commitment at the time. And we just started building products. And I went through, did lots of mistakes. I got some great mentors back in the day and I was just enjoying that kind of path of building and making and designing. And also strangely, as I reflect back on it now, was almost a very much startup journey. That digital division inside of a large publisher went from 10 to 200 people in 18 months with this huge scaling journey. We went from zero to many tens of millions of revenue in a short space of time too. And so yeah, that was where I started. That was where I got into design.
- Brendan Jarvis:
- I want to come back to what you said about professional football at the age of 16
- And draw, join a few dots between the being told that you weren't picked, so you had to confront the decision not to get picked up on a professional contract. And then this is perhaps me projecting or listening to what you're saying here. It sounds like given what you then went to study and then your travels abroad and how you sort of fell into design, it seems like you were a little lost in the years that immediately followed the decision or I suppose the rejection from professional football. Is that an unfair way of characterizing how things were for you? Did you see yourself as a teenager? You thought that you were going to the English Premier League?
- Alastair Simpson:
- Oh yeah. That hope. Yeah, for sure, Brendan, that was the hope. And I dunno whether, I'm just trying to, it's a super interesting question I'm trying to reflect on was I lost. I mean I think I was definitely searching for a new path, I think, and anybody who's 16 and is trying to search for a new path, how do you know? I think especially in today's day and age where many of the job titles that will be around in 10 years haven't been invented yet. They literally haven't been invented yet. And so 10 years ago, the thought of having an AI engineer didn't exist. So how is a 16 year old going to know that they want to be an AI engineer? And whilst design roles were around back then, I didn't necessarily know exactly what it was that I wanted to do. And so I think I was searching for a new path, but some of the things that helped me on that path were being curious.
- That was something that I was definitely interested in. And so going, traveling and exposing myself to different and new cultures was really inspiring for me. And that curiosity, the willingness when I went to college or university, I studied consumer behavior and psychology. And so that again started getting me thinking about, well, why did people do things? How do you make things that people want to use? How do you make things that people care about and why do people buy things? And so that curiosity to change the way I'd been thinking about my career in aver up until that point, I think has helped me tremendously through my kind of life. And again, it's really hard. I dunno whether I was lost at the time. Again, I'm not reacting to that word, I just don't know. As a 16 year old maybe I did feel lost because it was something I'd been working towards for 10, 11 years to do that.
- But as I said, you have to then adapt. And I think, I know that we talked a little bit about this prior to the show, it's like of course when you go through suffering or something doesn't go as planned there, everybody is going to go through a moment of this sucks. It always sucks and you're entitled to those moments. But then how you then respond to them I think is what's really important because you can actually learn a lot through those moments. And similar, you said, you know, mentioned the football, the rejection, but at 21, I was also rejected from three to five different graduates in London. And I could have been like, well this sucks. What am I going to do? And instead I took an opportunity, another door open to go traveling, which personally I credit for why I've been, had the opportunity to live all around the world because I said yes and I was curious. And that led me to different places. And I used it as a positive thing rather than looking and anchoring on it as, Hey, this sucks, this isn't in what's so terrible about it. And so I don't know that that's how I would characterize it. Brendan.
- Brendan Jarvis:
- Yeah, I think that's totally fair. Now this, we've talked about a little bit about rejection and there's rejection inherently baked into our education system. And I know that this is, as a father, this is something that you are particularly interested in. And the way in which you've decided to shape your children's education has been an alternative pathway to the ones that are most usually offered to most people. Before we get into the nuts and bolts of design leadership, you've previously said, and I'll quote you now before, I'm a designer, I'm a father, I have two young kids, Frankie and buddy. Now, kids are messy. They don't approach problems with process. They're inquisitive and they're creative by nature. And it's proven that giving kids unstructured playtime helps with creativity. Yet many parents and schools still structure their kids' time down to the minute. So thinking about what you said there, and now thinking about your role as a VP of design leading this large design organization at one of the most recognizable technology companies in the world, what role, if any, does creativity play in how you do your job?
- Alastair Simpson:
- Oh, such a great question. I love the quote. I mean, I dunno whether we'll talk more about education, but that's something that's been around and unchanged for kind of a hundred years, really to help people in go into roles that were in factories back in the day, or what I would actually term as complicated environments per se, where you have to follow checklists cause it's comp complicated versus I think the environment we're in now is complex and complex. You can't just logically apply a checklist to, right? You have to actually think, but I digress how it applies to my role as a design leader at a large company. I think it's about how you approach those problems that a company has and how you partner with different cross-functional partners to reframe the problem in a different light, to apply creativity in your designer mind to that specific problem. And that can help unlock new possibilities and new pathways, I think. And so that is how I would in a nutshell, kind of share how creativity affects how I think about problems and my role in a tech company. And I'll probably pause there and I'll let you dig into any aspect of that.
- Brendan Jarvis:
- Yeah, I know you've been working with other senior leaders at Dropbox on redesigning the future of work, and that initiative was sparked by the arrival of the pandemic, and it's been a key area of focus for you, and that's why I was curious around this notion of creativity and that cross cult, cross-cultural, cross discipline collaboration that you've been speaking of. But before we get into that, specifically thinking about what you said there about your children and the time in which time is organized or structured for children to learn traditionally versus ways that perhaps might be a bit more effective for them at the stage of life they're at, how structured is your time at work?
- Alastair Simpson:
- Yeah, it's a good question. I mean, my time at work, if I reflect back seven years ago, was very structured, so very, very structured back to back meetings constantly in very similar one-on-ones, very standardized kind of meeting cadences, very, very standardized. The journey for me to rethink that started when I was at Atlassian and I had teams. I was in California and then had teams in Australia, India, east coast of America, and I was on the west coast. And so trying to deal with those, all those different time zones is really, really complex. It's not easy, and of course you can just schedule around it, but you have to think, well, is there a better way to solve that problem? And so my time started to become less structured then because it was like, well, how can I progress the work asynchronously or in a different way?
- And I learned that to be honest, from Trello because Trello were fully remote from day one. And they were like, well, if we can resolve something asynchronously, then let's do that. But then if we need to raise the bandwidth to a synchronous meeting because we can't resolve it, then let's jump on a call so you'll c, time becomes less structured. And so that was really that evolution to where I'm at today where, yes, there is still some structure to my week, obviously I think you have to some, but then I do have larger blocks of unstructured time that are dedicated for deep work or deep thinking about specific problems. And also I try not to default to, oh, okay, well the expectation is there's a standing one-on-one with my direct reports every Monday this time. I'm like, why do you need that? Yes, we need to meet.
- There is always a time to meet and discuss things, but trying to get a bit more creative or to actually think through why you need to meet has been kind of a real thing for me and also for Dropbox, which as you said, we'll probably talk about in a moment. So yeah, my time now is a mix of structured and unstructured, but I do try to make sure that that structured time is a really definitive why, and then the unstructured time is there for deep work, deep thinking, or to jump into synchronous discussions if we need to do that.
- Brendan Jarvis:
- So speaking of synchronous discussions and meetings, zoom fatigue is a reality that I would imagine that everyone listening to us has experienced recently this impact that it's had on our lives. We've been thrown into this for a large time. For many people it was virtual only culture at work. And you've said about this, about the impact of meetings on people's lives. One of the most common reasons that we are overloaded is that we create too many synchronous meetings and we make it okay to constantly bombard each other with emails and instant messages. We've created a cultural norm where being back to back all day long equates to some badge of honor and the illusion of being effective. So given that you feel quite clearly, quite passionately about this topic, what does the meeting culture that you've tried to create at Dropbox, this virtual first Dropbox, what does that look like?
- Alastair Simpson:
- Yeah, so I mean probably once a slightly longer answer. I mean, when the pandemic happened, it was obviously incredibly unfortunate, so much devastation. But what we did think at Dropbox was that this was an opportunity to rethink and redesign how work, the Dropbox mission is to design an enlightened way of working. And so if you actually are intellectually honest, I think if you look back prior to the pandemic work wasn't super enlightened was, as I've mentioned, we're in back to back meetings, being busy is seen as good, whereas actually shouldn't it be about effectiveness, not just being busy. The advent of technology, things like messaging platforms, email has just stretched the day. So nine through five was an advent from the factory days, factory work from the Industrial Revolution. Technology just enabled that to go from seven through eight or all day, all night if you wanted, it didn't actually bring us more effective time to make us more productive in our roles.
- It just lengthened the amount of time that was expected of us at work. And so when the pandemic happened, as destructive as it was, we used that as an opportunity to essentially challenge all of those assumptions about why work happens nine through five in the same place. Why does we just have an eight hour block where it's just normal to go to work and to challenge many of the other assumptions that we had. Certainly prior to the pandemic, many large companies were saying, well, remote won't work for us. It's okay for a small company, but we're too big. And it's like, that's just an assumption. Let's actually, there's no data behind that. And then what's happened since then is you've seen a lot of companies embracing different models of work, but Dropbox, how we've tried to structure coming to your questions around meetings is the Dropbox model is called virtual first.
- And I'll just explain it. It means that virtual or remote is our primary way of working. So that's predominantly how we are talking now and how you'd have the majority of the meetings. We do have a belief that it's important to have moments where you meet in person. We do believe that that is a very foundational piece of work, just you really need to be intentional about why and how you're meeting. And so we try to talk about that as intentional moments of meaningful c collaboration or culture building essentially when we really need to discuss something in person, let's really do that, not just because it's a specific day of the week or whatever it might be. And so within that model of remote and then some access to in-person time, we've also broken up the day so that we've created what we call core collaboration hours, which is nine through one, which is where you're in your local time zone.
- So it could be different depending on where you are in the world. But nine through one for me in San Francisco, I'm expected to be online through nine through one for synchronous moments of collaboration digitally. So it could be answering Slack in a timely manner, email meetings, brainstorms, whatever it might be outside of nine through one, we encourage employees to create their own non-linear workdays. So if you want to work one through five, if that works for you, that's fine. If you want to take a break to go for a walk, if you need to do childcare, whatever it might be, and then you want to work in the evenings, that's totally fine. Or if you want to work early before nine through one, that's totally fine too. We're giving people the flexibility to focus on their outcomes, not just working between nine through five. Right. And just to be clear, we're not making the day only four hours long. We're saying, no, you need to achieve the outcomes that you stated for the business, but how you do that, we're giving you more flexibility
- Brendan Jarvis:
- Around just on the Celest, I know that previously you've said something to the effect, and I believe the word abhorrent is the one that you used that you believed it was apparent when companies, and I'm not suggesting Dropbox does this, when companies track their employees time, and I think you were speaking in the context of monitoring their company devices to know whether or not they're working this ability to after one o'clock in your local time zone to spend your time or invest it in a way that you see fit but still have to achieve the objectives that you've committed to. Is this with respect to the employment agreement where often we have employment agreements which state a number of hours that people have to work, is there an internal expectation that hours will be met or have you completely divorced the concept of hours that your contractor to work from the objectives of the outcomes that you're actually seeking?
- Alastair Simpson:
- I actually would need to double check whether we change the contract. I think the contractors actually remained the same. It's just the generic wording. And I think actually in different countries we can only state different things. So it's more though the cultural expectation around focus on outcomes. That's what we're trying to focus on, the outcomes for the business and for our customers. That's really what we want to individuals to focus on because ultimately that's what we should be going back to that busyness kind of comment. We've said busy is good, but we didn't say does busy equal effective for the business and for the customer. And so what we are really focused on is not busyness is are you being effective in your role and are you achieving good outcomes for our customer and for the business? And so that's really where we focus. Coming back to this synchronous time that you asked about in meetings, one of the other things that we've given employee, because what we've tried to help employees with is when we started rolling this out, we treated it almost like a product.
- That's was my involvement. I was co-leading this with hr, so myself and HR were co-leading this. And typically in most companies it's an HR initiative. It's like policy and process, whereas Dropbox approached it more like a product and how do you actually iterate and retain a learning mindset through this knowing that we may not have all of the answers. And that was how we communicated it to our employees. And we started rolling out what we did, small pilots. So it was like, okay, we're going to roll out to 60 people, this concept of core collaboration hours. We had a qualitative researcher following these people, what could we learn from these employees? What worked really well? And what came back were really heartwarming qualitative anecdotes around caregivers who no longer felt guilty about having lunch with dinner with their kids, whilst also being a contribute really meaningfully to their work.
- But what also came back clearly was, okay, I get it core collaboration hours, but how do I have less meetings physically? How tangibly how? Because when you dig into it, there's like a hundred years of ingrained habits here about how work gets done that you're trying to break. It's nothing to do with Dropbox, it's just how we've as assumed work gets done. And so one of the important things we learned from that was giving people almost scaffolding or frameworks to help them diagnose and break down some of these problems. You can all look these up. The virtual first toolkit, which is externalized is 20 step-by-step guides for how you change habits. And it's somewhat design thinking at play, right? Because it's all based out of research and lessons that we learn from listening to our employees to help them understand how and when should I meet.
- And so one of the really interesting acronyms that we use internally is kind of the three synchronous time should be reserved or meetings essentially should be reserved for important decisions, important discussion or important debate. It's a very simple thing. And too often meetings, the reflexes, okay, we'll just schedule a meeting for that where it's like, well, what are you trying to do in that meeting? It's like, oh, it's a status update. Well, don't, not discussing debating or deciding anything, so why there's must be a better medium for how you can communicate. But again, the habit is just reflexively schedule a meeting, reflexively schedule a meeting. And so we're trying to break those things down. And then we've even gone so far based on that research, we gave people permission to say no to meetings and we gave people short one-liners for how to respond to meetings that didn't have an agenda, that didn't have a clear outcome. And again, we gave people permission to say, Hey, is there a better way to solve this essentially? And can we start asynchronous before moving synchronous? And that was again, one of the kind of behavior shifts that we were trying to marry to was going from synchronous by default to asynchronous by default. And so that those kind of different behaviors are very interesting.
- Brendan Jarvis:
- I can see how saying to a peer, Hey, this doesn't seem like this warrants a meeting. Let's explore another way of achieving the outcome that you're seeking. I can see how you can couch that and that can be useful in reducing the load, the meeting load that people are under. How, if at all, have you tried to shape the culture or shape the ability for people to communicate that when there's a status and balance at play? So if say that I'm one of your, I don't know, principal designers and I'm communicating with you about something, you say, let's have a meeting about it. Where does that leave me and my ability to address that status and balance?
- Alastair Simpson:
- Of course. It's a good question. And what we noticed, again from our research and when we looked at internal data and something that we proactively tried to do is you need to model the right behaviors from the top down and can never, I don't believe anything can just be tops down. I don't think that really works. You need a bottoms up, but you do need leaders to model the right behaviors. And so whilst we are now seeing tremendous results with virtual first, I think the most recent stats are 78% of employees feel more effective in virtual first than they did prior. 84% of meetings happen within the core collaboration hours kind of window. But certainly it didn't always look like that. I'm not going to say it was just rosy from day one. It was difficult from day one. But when we started to look again, intentionally treating it like a product, if you start diagnosing which teams are doing really well with virtual first and what you noticed when you just went and did research even you could do surveys, but even just going and talking to people, it was often down to the manager or the leader like, oh, well we are really succeeding in virtual first because insert name has really helped model the behaviors that they expect from the top down and that goes all the way up to the top.
- But what we then did was based, again, one of the principles, we wanted to take a learning mindset to this. So we rolled it out, got some feedback, it was working in some areas, not working in others. What we did was then when investigated, why is it working here? Why is it not working there? And one of the big lessons that we got from that research was managers play an outside role in how they shape culture in the teams, and whether that's a virtual first culture or a performance based culture, whatever type of culture you're trying to create, managers make an outsized kind of impact on that both positively and negatively. And so then based on those lessons, we're like, okay, we need to target that cohort of managers and arm them with the why behind the virtual first model. Because again, when you go and talk to some of those managers about why they weren't adopting it, they didn't understand why, and there's obviously famous books on start with why.
- And so that was what was really key. And so we then started to roll out quarterly manager training. How do you actually adopt virtual first practices? All weaved into the kind of quarterly manager training. We started doing regular communications and consolidated communications to really help shape employees' perception of where we were trying to get to. And also targeted at managers about how they played that outside role and give them training and lessons and how to adopt virtual first. And so that was really, really important because I agree with you, if your manager's not modeling those behaviors, then how else are you supposed to as someone in that team? And we did lots of other things, like I posted my calendar on our internal blog, which was totally open with how I was adjusting to virtual First. We had other key leaders post how they were adjusting to virtual first. And so lots of different microt tactics to all ladder up to the kind of why behind we were changing the way of working and where we were trying to get to with virtual First.
- Brendan Jarvis:
- I had a conversation with Jeff Gut Health last week I think, and we were speaking about one of his observations, consulting to enterprise, and that there's often a communication effort to try and change behavior and culture, but in his observation, what's often forgotten is the way in which people are incentivized, which also shapes their behavior. What changes to the way people are incentivized at Dropbox? Did you have to make or did you make any in order to make it easier for people to feel like they could adopt this new virtual first way of working?
- Alastair Simpson:
- Yeah, I certainly do agree with the incentives point. The one thing that I will double down on with the communication though is two things, is that why are we going towards this? Really helping employees understand that deep why I think really helped us as a company. And so just talking through the different reasons why we're behind it. The second thing that really helped us was we shared publicly as part of or publicly, externally, and also internally, Hey, we're on a journey and there are five behaviors that we believe we need to go from two as a company. And so it was things like syncs all day, which are synchronous meetings all day to working asynchronous by default. So that's what we were trying to change and this culture going from busyness to impact, how do I be really impactful versus just being? And so that framing around the behaviors that we were trying to change, I can tell you from our experience resonated very deeply with employers because they were like, oh, I get it.
- I get why you're trying to do these things and this really helps me understand that I'm not alone, that we're all going through these behavior shifts together and I need to go from here to here. There's some steps that I can take and it won't happen overnight, but hopefully we we'll get there. And so just doubling down on that communication, I think those why and the behavior changes was really critical for us. But certainly coming to your incentives point, because I don't disagree, some of the things that we changed not early on, not early on, but some of the things we have recently changed are we have obviously career ladders and career frame and career frameworks internally. And so we've had to adjust the language in those and because they're obviously an incentive because every six months that's how we grade our employees. And so those kind of incentive structures are ways that we have slowly over time tried to make sure that the incentives for every single manager and individual contributor are aligned to kind of our way of working. But they were something that happened after they didn't happen early on. Yeah, but that is what we've changed from
- Brendan Jarvis:
- This move to virtual first and you start at Dropbox in 2020, the world completely implodes around the same time you possibly, you thought you were going to be at headquarters and you'd have a big team there and life was going to be different for everyone, all of us, and then it wasn't, right? This is a large design effort. You mentioned that you partnered with HR on doing this, but this isn't what people typically think of when they're thinking of a VP of design at a product-led company. You don't normally think, Hey, let's just completely design the culture of work and the way that we are working as well. And it's a magnificent example of design being applied to a rather wicked problem that's outside the context of product. And I've heard you talk about your role as VP of design and you've said, and I'll quote you again now, I see my charter as designing across the seams of our organization and making sure that the end-to-end experience and the promise that we give customers at any touchpoint has lived throughout that customer life cycle. Why have you at least it seems defined, your role so broadly?
- Alastair Simpson:
- I mean, think there's a number of, I'll start on the pandemic just to give everyone the full picture slice. My first day at Dropbox was March 24th, 2020, which for those that remember, it's literally about 12 days after the US borders closed, and every person, my laptop is mailed to me and they're like, don't worry, we'll be back in a few weeks.
- Brendan Jarvis:
- Yeah, it'll all be fine.
- Alastair Simpson:
- It'll be fine. We'll be back in the office. And then 18 months later, I still hadn't met anybody in person, I think. But coming to your question about, and I will say that when I joined Dropbox, I did not think this was going to be the first design problem that I would be solving, but the pandemic created a confluence of events that landed with the virtual first. Kind of my co-leading that the charter question brought about being so broad though is I'll use a term that I don't really like, but designers have always wanted this seed at the table. I don't like that term though, to be honest, but designers have wanted that. But what I have quite often seen, and when I mentor people, designers do have that seat, but then when they have that seat, it's like quite often they don't know necessarily know how to engage with the business folk in the room or with the marketing folk in the room or with different cross-functional partners, which as you become an executive design leader and you've got thousands of people and very senior executives beside you, I think whilst you'll always have your deep domain in design that you need to be accountable for in the user experience, I think more at that executive level, you have to be a strong cross-functional partner for your peers.
- You have to be, and I can't remember, we touched on this earlier, we definitely touched on this, but it's like I think that applying the way you think about the problem, so applying creativity, applying a reframing to the problem and questioning the problem and questioning the assumptions that the business is made can be very helpful at that executive level to help your partner in who might be the C F O or the chief people officer or the chief product officer or the CTO O think differently about how to solve that problem. And certainly this virtual first is a good example where when the opportunity came up personally, I was like, look, to me, this is a design problem. This is human behavior and changing human behavior. And you can approach this in a design specific way or design thinking in a human-centered design way. But then I also wanted to engage, so I talked to Mel, our chief people officer about why I thought that and why how we could help.
- I wasn't trying to expand my remit and create a fiefdom or a kingdom or anything like that. It was just how can I apply my designer mindset to a problem that the business has that is going to be incredibly critical in shaping the kind of future of Dropbox. And so that was my intention. And just by reaching out across the aisles, designing across seams, being a strong partner, I feel quite proud that we've had such a positive impact on Dropbox's lives and the way in which we are thinking about this future of work. So that's kind of why I see that remit as quite broad, but it's more about engagement with those cross-functional partners. Be curious. I've mentioned that a few times. Be curious, ask questions. How might you help your partners think about a problem differently? And that's really what I'm passionate about, just applying that design mindset to different types of large scale problems and small scale problems that are have in the design team.
- Brendan Jarvis:
- And that sounds really nice and sounds like a really appropriate and sensible thing to be doing when you are the most senior design leader at a company to be reaching across the aisles to be asking questions. But there's some nuance here because questions, I think Sam Ladner, who's a principal researcher at Workday, describe them to me as, or the why question as a three letter world destroyer. So you can use questions for both good and for bad, or they can be interpreted in different ways depending on how you ask them or the approach that you take. So fill me in here, what you're at the risk of being perceived, at least to be expanding your remit past what it may be in your job description. You're at risk of standing on people's toes here. You are new to the company, so you don't have necessarily the relational capital yet established. Yeah. What were the finer points of the approach? How do you open up those conversations? What is the thing or things that you can point to that you feel made you effective as the design leader in that conversation in that context?
- Alastair Simpson:
- It's a very good, great point. I haven't heard the why question is, what did Sam call it?
- Brendan Jarvis:
- Three letter. The three letter world destroyer.
- Alastair Simpson:
- Great. I like that. I might start using that. The thing that I come back to, well, firstly, let me, my experience at Atlassian where I managed remote teams and had to build relationships with remote employees, people that worked for me, partners really helped Stanley in good stead for when I joined Dropbox and the world was just fully remote. I was like, okay, well, whilst I had an office in Mountain View that I did go to most days, the majority of my team were remote. I was building relationships remote. So I had a bunch of tactics already, like I've mentioned, working asynchronous by default. And what that means is keeping a confluence page or now a Dropbox paper document where you can, with an employee, where you can consolidate information, not slack, because Slack instant messaging is great, but it can also be destructive, like quite interruptive, but consolidating documents into one page PDA or a Confluence, confluence page.
- And we can work asynchronously in our time zones to move work forward. But if you can do that, you start, that's a tactic. You can start actually building up trust with people because you can actually move work forward. You can also destroy trust in those environments. But what I learned, and what I mean by that is if you would've done this, pick your tool of choice, JIRA, Asana, Dropbox, paper, tr confluence. When you get 20 deep in a comment thread where it's just like people going back and forth eroding trust there, because the, the meaning behind what you're saying is getting lost. And what I learned though from that experience is you have to understand when to raise the bandwidth. So stop eroding trust and say, Hey, time out. Let's just talk synchronously about this. Let's just jump on a call because we'll probably resolve it.
- And you will then build trust. And I made my share of mistakes at are Atlassian non eroding trust, but I learned from those in terms of how do you build trust? And so those are more tactics though about how you build trust. The thing that I ladder up to is how I think about building trust and relationships in general, which is more of a framework around when you're sharing information, is what you're sharing credible. So it's not just your opinion, Alastair opinion says, right? It's like, no, this may be my opinion, but it's informed by this set of data, this experience, this et cetera thing. So is what you're saying credible? Can you back it up with some form of data? Then are you reliable as a partner? Okay, so I meet with you, Brendan, I'm going to get back to you by the end of the week.
- Do I get back to you by the end of the week, right? Do I actually follow through all my promises, right? Then if you're thinking about it like an equation, which I often do, it's divided by showing that you care. And what I mean by that is when we take our introductory chat, we jumped on, we didn't just say, how are you? And then jump into the first thing. We actually were like, how are you? How's your day? Then you listened, and I've mentioned this, you actively listen. Then you ask a follow on question. Then you may ask another following question. So you're showing that you care about that person. You're not just not performative, that you're just like, how are you? Great. Let's go straight to the action, right? Because then don't, you're not showing any empathy you have, we're all humans and you know, talked about me being a father, I'm a father, a failed professional footballer. I'm a brother, I'm sorry about
- Brendan Jarvis:
- That.
- Alastair Simpson:
- I know, and lots of these things that you are too. And so we are just humans as well as the job that we have. So showing that you care. So those three things, credibility, reliability, showing that you care, help you build trust, in my opinion. And so coming to your question about how did this work, certainly wasn't just sitting in meetings going, well, that approach is wrong. Let me tell you why this is not going to work. It was a genuine curiosity. And then when I did share information, it was like, and I actually had, I was fortunate that Atlassian I did not create, but I was a big advocate for something called the team playbook that Atlassian had. And so I'd seen how that had changed people's behavior. And so how it had actually really helped change the way that we built products. And so I shared information and statistics, credible information about how that had helped change culture.
- And then that tweaked an interest in Mel who wanted to me to explain more. And then so you start building up these different kind of relationships in that way. But that's how I generally think about networking, building relationships is that kind of credibility, reliability, showing that you care, building that empathy for people. And again, there's lots of tactics underneath that that allow you to do that, whether you are remote or if you're in person too, right? We've all had this, it's a silly one, but when you meet in person, do you have your phone on the table so that you're constantly checking it? That shows that you don't really care unless you are like, Hey, I'm expecting a very urgent family call or something. There's a legitimate reason. It's just like there because I'm not present with you. And so I think those are all small things that we miss in this kind of virtual or
- Brendan Jarvis:
- Physical world. You spoke about Mel, Mel, is she the chief people officer?
- Alastair Simpson:
- Yeah, she's the cpa, the chief people officer. Yeah.
- Brendan Jarvis:
- Right. So you talked there about credibility being one of those three components and how you had been across the playbook at Atlassian and were able to bring some of that knowledge into the conversation, but it almost sounded as if rather than directly declaring an intention or an interest here, clearly you were obviously interested in the topic of virtual first and how you were going to do that, but it almost sounded to me like you were sowing seeds in a way that other people became curious and interested in what you might have to contribute to this problem. Yeah,
- Alastair Simpson:
- Absolutely. Like sewing seeds are actually used with many of my team because it's something you're trying to do over time. You're trying to actually, again, as you become not necessarily even more senior, but if you start managing people, you don't just want to tell them what to do, right? Because there's, that's just taking away people's autonomy. But you may have an opinion that you might want them to follow, so how do you sow that seed in them? And so yes, definitely that is something that I think is very important. And then again, sowing the seed of not just the playbook, but also, okay, treat it like a product before we roll core collaboration hours out to 3000 people. How do we roll that out to a small group and learn? Did it work? It's like hypothesis, right? You're building a product. What was your hypothesis?
- Our hypothesis was this, we ran a small test, it performed awesome, or it performed terribly or it performed somewhere in between. And this is what we learned. Okay, great, we learned something. How do you iterate on that and actually take the good stuff and try and mitigate the things that don't work? And so just that way of working. And I think though, the other thing I'd say on that is you're sowing seeds. I think that's definitely a good, great observation, Brendan, but you're also, you're just being genuine about, okay, I want the same outcome. Here's some ideas, credible ideas and reliability behind those ideas of how you might think about it so we can get to a better outcome together. Because again, you've meant, we've talked a little bit about the football, but honestly I learned from that building. Well, football is a team sport.
- You win and lose as a team, and building product and building companies is the same. It's a team sport, and you win or lose as a team. There shouldn't be any finger pointing. And so that I think is something that I think was invaluable in building that relationship. And then also, again, just teasing it out a little bit more, my initial involvement, okay, you're, it was, can you deliver this one component? And it was the toolkit. And my team, again, a kudos to my team actually, if anyone's listening. So it's helpful. There's a remotely curious podcast that we publish. It's excellent if you want to go and listen to some great insights into how we built that and working remotely, it's really awesome. But the team then delivered a really good first version of the toolkit. And so shipping something small helped build trust with a wider audience versus try coming in and saying, oh, I think we should own the whole thing. And it was like, okay, let me help you with this bit and then let me build trust that way.
- Brendan Jarvis:
- That's a really key point that you're making is that you don't try and hit the home run necessarily the first time you are building. You were talking about the credibility of information, but you're also building your own credibility, and that's feeding into what you're speaking there about how you generate trust. And there are a number of tactics, which you've quite eloquently described there. I want to come back to your feelings on the term that is often used in design circles, which you touched on, which is getting the seat at the table. Yeah. What is it about that framing that irks you? What is it that you don't like about that framing?
- Alastair Simpson:
- It's as if there's some mythical, literal, physical table. All the decisions get made, and you as a designer have no way of influencing anything that goes on there. I just think that we just talked about that, but it's like if you're intentional, you're genuine, you're showing great work, you can have more influence whether there's a table or not. So that kind of irks me. That's the first reason that it irks me a little bit. And I think we often forget that we have more power and more agency over our future than we think I do. Believe that. The second reason that irks me is that I think design has had that seat for a while, but I worry that we don't know how to engage there. And that is actually a detriment to our discipline. And don't get me wrong, as much as I think a design leader is a business leader, we also have a deep accountability to building, designing great product.
- That is our core kind of tea thing. But I think when we get to that table, we again, it's like, oh, well what's being discussed is business talk, so I'm going to switch off or I dunno how to engage in that. And it's like, no, if you're at a large, any size company and you're at that table, you have a responsibility to understand, okay, what is being discussed? Why? What is happening with net new a r r? What is happening with churn? What are these topics that are going on? We're shifting to virtual first. What does that mean? How is that going to impact my team? And leaning in versus leaning out I think is the way to go personally. But yeah, they're the two reasons that generally irk me because again, I have spoken to designers, they're like, oh, I have the C, but I don't have the influence why I don't have the influence. It's like, well, are you leaning in? Are you being curious? Are you asking questions? And again, it's hard. Every situation is slightly different, but in general, the answers that get back are no, or what's being discussed there isn't design related. And it's like, okay, but design is a part of their business and the business as an overall needs to function and build great products for customers.
- Brendan Jarvis:
- Some people feel intimidated by that, by the business and the business conversation, the things that are outside of our discipline. But I get the sense that you found or you find these conversations intriguing and empowering rather than intimidating.
- Alastair Simpson:
- Totally. There's a Mike, Hannah Brooks, who co-founder El Sian. He gives wonderful Ted talk on imposter syndrome and Atlassian, if you're not, we're a huge jagonal Australian tech company, makers of Jira, Trello, confluence, but had a very rapid ascent. And Mike shares a story in there where he was around the table with investors, BC and different people. I think it was the first board meeting and they were talking, and literally he said he was taking notes. They thought he was taking notes, he was writing down words that he didn't know what they meant.
- Brendan Jarvis:
- Wow. Right.
- Alastair Simpson:
- But what he was doing was like, right, I don't understand it, but I'm going to go find out. And he was sharing, he had imposter syndrome and if he had imposter syndrome, just like wow. Because he is an incredibly impressive person. And I think we all have that, right? It's how you manage it. That is important. It's the same as, well, my analogy is public speaking people, I'm not a very good speaker. It's like that's just a skill you can learn. And also you have to learn how to manage anxiety well and manage nerves well. It's hard. I'm not suggesting it's easy, it's hard, but it's a skill you can learn if you're curious about that. And the similar thing with when there are discussions or conversations going on that I don't understand, it's like I'm going to ask questions and it might be hard to ask a question, but often a self kind of reference that I give myself is what if I feel scared about asking this question?
- It's probably a question that I should ask, right? Because actually it's probably too important to kind of let go and it's okay to kind of ask those questions and find out more information. Because again, coming back to design, design is understanding the need, right? Design is understanding the need of the business or the customer, and then designing a solution for that. So understand the need. You have to ask a lot of questions. You have to be curious. But I worry that, again, as a design discipline, we've lost that and it's like, oh, here's 50 solutions. And yes, we need generative solutions, but what's the problem? Do we understand the problem before we go design the solution? I often we don't.
- Brendan Jarvis:
- Alastair, that is a very important point and question to finish on. Thank you. This has been such an enjoyable conversation. I really appreciate how generous you've been with your stories and insights today. And also for continuing to bring a pragmatic, a compassionate, and a thoughtful lens to design leadership for the design community.
- Alastair Simpson:
- Oh, thank you so much, Brendan, for the kind words, and thank you for having me on the show. I appreciate you asking me on to share stories and anecdotes. No, it's been, hope you found them useful.
- Brendan Jarvis:
- It's been my pleasure. And if people want to keep up to date with what you are doing and your contributions to the field, what is the best way for them to do that?
- Alastair Simpson:
- LinkedIn is honestly the best one I would say right now. Yeah, LinkedIn. So definitely just add me on there. Please give some context. If you do add me, that's always helpful. Just add a short note.
- Brendan Jarvis:
- Yeah, a hundred percent. Thanks, Alastair, and to everyone who's been tuned in, it's been great having you here as well. Everything that we've covered will be in the show notes, including a link to Alastair's LinkedIn profile and all the chapters for all the topics that we've covered. They will be there too.
- If you've enjoyed the show and you want to hear more great conversations like this with world-class leaders in UX research, product management and design, then don't forget to leave a review on your favorite podcast app, subscribe so it turns up every two weeks in your feed. And also tell someone else could just be one person that you feel would benefit from these conversations at depth.
- If you want to reach out to me, you can find me on LinkedIn. There's a link to my profile on the show notes as well. Or you can head on over to my website, which is thespaceinbetween.co.nz. That's thespaceinbetween.co.nz. And until next time, keep being brave.