Alastair Simpson, Head of Design at Atlassian

Alastair Simpson, Head of Design at Atlassian

What does it take to be a great design leader? Ask Alastair Simpson, Head of Design at Atlassian, and his answers may surprise you. To Alastair, great leadership—and great design—come down to communication. Journeying from his first job at a call center to the helm of a 70-person design team, Alastair has found communication to be the linchpin of success.

As a design leader, Alastair also shrugs off top-down decision making. His goal is to make zero decisions for his team. Tune in to learn more about his leadership approach, how direct feedback can make you a better leader and the importance of having a real life outside of your job.


Show Notes

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Carl: Hey, everybody and welcome back to the Bureau Briefing. You know, when you hear the phrase design leader, when you think about somebody who's a design leader, you may have a vision of a knight in shining armor who's leading a charge, or you may think of a shattered human being laying under their desk sobbing quietly. Well, today, we have got on the show the head of design at Atlassian who manages 70 designers. He's a friend from Design Leadership Camp and a speaker at the first design leadership days, and he's going to shed some light on what it is to be a design leader. It's Alastair Simpson. How's it going, Alastair?

Alastair: Very well, Carl. I'm crawling out from underneath my desk as we speak. No, I'm very well. I've just got back from holiday, so I feel very refreshed and energized. It's great to be part of the show today.

Carl: Well, that's great. Well, tell everybody a little bit about your background. I know you've managed large teams and small teams, but just tell everybody a little bit about how you got to your role today.

Alastair: Yeah. The story... I guess I don't have the quintessential designer story of, you know, going to art or design school and then growing up through the design ranks. But I was telling... We just had 60 new graduate start at Atlassian yesterday, and we did a Q and A with some of the CV leaders with them and were asked what our first job was. My first job was when I was backpacking around the world, and I was working in a call center.

Carl: Oh wow.

Alastair: But the reason I told that story was because I understood working in a call center doing outbound sales and then inbound customer service, you realize pretty quickly the communication is an incredibly important part of your job and how communication can really make or break any conversation that you have. It's a personal belief that I have around design leadership that communication can make or break any design project that you're working on. That was kind of my first job, but you know, I pretty quickly got into more traditional design roles, became a design team of one at a large business to business publisher back in the days when we were migrating print classifieds and print publications to the internet.

Carl: The good old days.

Alastair: The good old days and trying to figure that out when print publication revenues were going massively down. Again, I was telling this story the other day. We were growing the online revenues 10000%, but online revenues was coming from zero to half a million. The percentages looked great, but the revenue when compared to the downfall of print. But I was a design team of one, so I got to do pretty much everything, build my own usability testing labs, branding, visual design, interaction design, made loads of mistakes, and then eventually, grew up to manage a team and then manage a lot of external agencies in that role, getting a lot of external subject matter experts in to to help us.

Then prior to Atlassian, I was a consultant for my sins. I was running a small design team working on large connected device work is what we called it. I didn't really do any desktop work before Atlassian. It was all in flight entertainment and streaming media on gaming consoles and mobile and tablet, and then understanding again the importance of communication as a consultant coming into clients and communicating effectively to them. Then I joined Atlassian and my journey at Atlassian has been... I've had the pleasure or misfortune, depends which way you look at this fact, of I've actually worked on every single one of the Atlassian's cloud products.

I've run design teams on HipChat, Stride before we end of life those products, Dura Software, Bitbucket, SourceTree, Trello, Confluence, and then I run a number of cross products platform teams like the Atlassian cloud platform growth team now. That's kind of ended me up where I am today. I originally started my career in England, lived and worked for 12 years in Australia, and then moved to Mountain View about a year and a half ago with myself and my family to continue working for Atlassian here. That's kind of where I've ended up today.

Carl: It's quite a journey. Now, I want understand a little bit more about the call center as your point of origin. Was that making ends meet or did you not know what you wanted to so you grabbed that job? Like what was it?

Alastair: Again, I haven't given this thought externally. I've given it internally to the Atlassian design team about... The talk's called Communication Lessons from the ShamWow Commercial. If you're familiar with the ShamWow or if you're not and you're listening, it was a very famous infomercial in the early 2000s that was incredibly cheesy, but they essentially selling dish dishcloths and, but they made hundreds of millions of dollars. If you watched the infomercial and then the talk I give, I break it down into the communications framework that he's using. It's incredibly powerful the framework that he uses there, and so I've given that talk. But yes, so understanding where it is.

At the start of that talk, I tell the story of why I was working in a call center and essentially I finished university. I'd done a degree in maybe business, but I've done a lot of consumer behavior and psychology and why people do things and why people buy things, which is how I got into design. I'd finished university and I went traveling around the world for a year. I traveled in South America and New Zealand, Australia, Southeast Asia, and then at the end of the trip, me and my best mate Adam, we were in Thailand, in Bangkok, and we were like, are we ready to go home, back to England, and get real jobs in inverted commas.

We both looked at each other and said, "Not really." We quite enjoyed Australia and we've made some good friends there that we traveled with in South America who are now back in Sydney. I'd already borrowed some money of Adam and I only had about, and this is not an exaggerated story, I only had about 200 pounds left in my account. We decided though to fly back to Sydney and use our working holiday visa to get to get a job. Pretty much on a working holiday visa back in the early 2000s, you're pretty restricted on what jobs you could do. Both of us only had a degree. We didn't really have any work experience. Really the jobs were stop people in the streets and try and get them to sign up to charities. You could work as a laborer on a building site, or you could go and work in a call center

You could actually go and work in a bar, but to work in a bar in Australia, you have to have a Responsible Service of Alcohol license, which costs about $250. we didn't really have the money to do that. Both Adam and I went down to the call center route because I guess, you know, I've always been a very sociable person. I love interacting with people, and so we went into the call center route and we had various jobs, outbound sales, inbound customer service. It was really... To your point, we didn't have any money left in our accounts. We had to get jobs because we had to pay rent, and we had to get by and live. It was just we're going to go and do it, but as I said, I still look back fondly on those days, and I still keep in touch with many people that I work with there.

As I said, I firmly believe that a lot of the communication techniques that I was taught and learned there have been really quite pivotal in my jobs today and how I still counsel designers and design leaders that the number one thing that they need to kind of focus on is communications. I think it's my own personal belief. I vaguely think that I read this somewhere and if anybody who's listening can actually verify that this is out there somewhere, then please send it to me because I've never been able to find it since, but I have a personal belief that design is really 90% communication and 10% doing the work. That's not to say that you can communicate that work and then ship it and it'll be wonderful.

You can't. You can't communicate your way of bad work that doesn't solve customer problems, but I do. I've seen many designers who've done amazing work, but they failed to communicate that value effectively to stakeholders or to customers and that can let people down. As I said, I counseled people today to spend more time thinking about their communication, how their building an argument and how they're talking through their work because I think it's a foundational skill that we all need I think as humans and certainly we all need as designers and as members of cross functional teams.

Carl: Totally agree on the importance of communication. I think it's within design, it's within the whole human experience. Everything that we try to do for poor communicators, for some reason we have bad luck. Things never seem to go our way. But if we're great communicators and people understand, wow, look at how I'm accelerating and things are going great. So real quick, I have one more question about the call center, when you work there and you started making some money... I think this is almost always true. When you have that first job, you start making some money, it feels like the world is yours. Then you advanced to this really big career, probably making a thousand times what you made then, but you always feel stressed for money.

Do you have this experience where when you were at the call center, you were out with your mates every night and you're having fun and now you're kind of like, "How are we going to figure this out?"

Alastair: Back in those days, I remember I think... My rent each week was $145 and I earned about $590 a week. I could earn more if we did commissions, but the base kind of pay. In my head every week I was like, "I've got $450 to spend." Like that's just free money because I didn't have any other commitments at the time from a financial point of view. That was literally it. It was like you do the percentages on that. You've got a huge large disposable income. But now today it's like it's coming in, but then it's going out.

Carl: But where's it going? I got elevated at this company I was working at to a senior vice president position when I was in my mid twenties, and I remember somebody said, "What are you doing with that money?" I said, "Oh, I still live paycheck to paycheck." Life just got really good, so I'm not the best for that. Then I've just got to know what happened to Adam?

Alastair: Adam, my best, still in touch with him. I was his best man at his wedding and from years ago. He's probably not listening to this. He's not a designer, but he actually... After we finished our year in Australia in 2004, we traveled for a year together, lived in Australia for a year together, and then we both moved back to London and work together. Then I actually moved back to Australia in 2006 and then in that same year he moved back as well. He lived in Sydney for about five years and then he moved to New York. He moved to New York roughly 2011-2012. He's now living and working in New York for I forget the name of the company, but he's a SVP in sales for a tech company who's doing kind of online chat for banks. We're still very much connected. Very much still in communication, so yeah.

Carl: Okay. You both elevated in your careers and you did pay him back the money that you owed him?

Alastair: It's a long time ago, so I think so. He definitely bailed me out back then, so yeah, but I think I paid him back.

Carl: Well, let's talk about what it's like now to have 70 people on your team, but that's not all that you're managing. You're also managing other parts of the company. You have all these different product leads I'm sure. What is a day in the life like for Alastair Simpson?

Alastair: Every day is different to be honest. Every day is different. There's actually a post that I've shared on the Atlassian blog around managing my calendar. So I know that you're not looking for the in exactly, but there is a post in the Atlassian blog about managing my calendar because I do try and have specific days for specific things. Like I will back to back my one-on-ones with my design leaders on the same day as much as possible so that I get through those things in a block. But I mean, a day to day for me really is I spend the majority of my time really working with my cross functional partners if I really look at my day to day, the VP of product that I work with, Joff Redfern, the head of engineering, Steve Deasy. We see ourselves as running our business.

The portfolio that we run, we see ourselves as running that business. The three of us spend a lot of time looking at the strategies for each of the products that we have in our portfolio, are those strategies set well and then are the teams set up to execute really well. We then spend a lot of time looking at the metrics that are coming into the business. Every week we have what's called a Tashi that comes in from the strategy and business ops team that tells us the health of the business and that includes customer centric numbers as well. Not just revenue numbers, but customer centric numbers. You know, how happy a customer is using the product. Are there any hotspots that we need to look at?

Are there any major call outs that we're shipping something new to our customers and what do we expect as the impacts of those things to be? Really a lot of the day to day for me now is managing what I see is the business, the portfolio, that we run. Then obviously as well outside of that is coaching and developing the managers that run those businesses for me. Again, I have this belief around leadership. I've moved out of an individual contributor role a number of years ago because I believe that I can have a larger impact by coaching and developing people to do amazing work.

A lot of my time is spent in one-on-ones with my team talking through the problems that they have, talking through how they're approaching particular problems and how they're working with their product and engineering partners, and then trying to coach and development develop them through those situations and guide them really because I don't want to lean in and make all of the... Actually my goal really is to make zero decisions for them. That is actually my goal is I don't want to make design decisions or decisions for them. I want to help empower them because they're their senior leaders in their own rights and they're running big programs. You know yourself.

People want autonomy and mastery over their own destiny. They don't want to be micromanaged. A lot of my time is spent each week in one-on-ones and you know, coaching, mentoring them through particular situations that they're finding themselves in and then trying to in that environment, in our one-on-one trying to, not necessarily role play, but go back and forth and critique and sparse some of the decisions they're making. These are not all design decisions. Obviously we look at design in our one-on-ones and what are the key things that we're going to ship to our customers and why do we think these are the most important things to be focused on, but also critiquing how they're working with their cross functional partners because I think that's how the majority of products get built today.

It's not in a silo of just product or just engineering or just design. It's working collaboratively together with your partners to ship something amazing for your customers.

Carl: When you get to that higher elevation, that new vantage point, that's when you can create that really holistic experience for your customers, right? I'm curious, what was the most difficult part to remove yourself from that more executional role and get yourself into that coaching role? Because I hear people say all the time, "Just when I think I was out, they pull me back in," right? It's that make or manager and it's not just design either. It's just leaders in general. What was the most difficult thing for you when you made that transition to more of a coach?

Alastair: It's a good question. You're right, it's something that many people ask about. I think from a personal point of view, I think reflecting back when I first took on a larger management role, I kind of cringe a little bit as to some of the things that I did back then. I spent a little bit of time being that micro manager and trying to make too many decisions in my team. The thing that I think was pivotal for me was really listening to... Well, sorry, firstly asking for and then listening to the feedback that my direct reports were giving me because I started a number of years ago asking for feedback every single quarter. Then when I really started listening to that, it was painful to be honest.

It was difficult to hear-

Carl: Right.

Alastair: ...because they were saying things that... They were like, "Hey, you kind of suck at this." My initial reaction is... I think it's a natural reaction. Your initial reaction is that's not true. I don't behave like that.

Carl: You have no idea what you're talking about.

Alastair: When you actually take that little step backwards and say, "Okay. I've got over the initial annoyance that somebody is giving me this direct feedback, but actually is the example they're giving me a true example," and then you say, "Actually, yes, it is." I think that was probably the pivotal moment for me to realize that, hey, I probably need to change here and I probably need to start listening and start empowering those leaders to deliver on the things that we've hired them for. Because as I said, they're senior managers in their own right and they deserve to make their own decisions and drive their own destiny.

My role in this now is much more of a guide and much more of a coach. As I said, I'm much more of a mentor. I think to your question what was the point, I think it was when I really started actively asking for and then listening to that feedback. You have these low points where you're listening to it and you're like, "Wow. There's some pretty direct feedback in here." But I think if you really look inside yourself, at those lowest points, that's when you can learn the most and you can change the most as a leader. You can actually say, "Right. I'm pretty low right now. I've got all of this direct feedback, but this is good feedback that I need to now choose to listen to and to change my own behaviors."

I think it's how you choose to react to specific situations is more important than the situation that you find yourself in, you know?

Carl: Wow, that's amazing advice. Thank you for sharing that. I have to wonder, when you have all of that weight on you and all of that feedback and you're trying to get yourself in a position to be able to see it, how do you stay positive? Who coaches you?

Alastair: You've got to find the things outside of being a design leader that are going to keep you healthy and positive. One thing for me certainly again working... Well, I'll come to that in a bit actually, but find the things that are outside of being a design leader. You don't want your job actually. It's not just a designer leader. You don't want your job to define you. You need to be a person, a holistic person, outside of your job. I think that's incredibly important. For me, those people that keep me grounded, my family, my friends, my kids, and also having activities outside of my day to day job. For a number of years, I played semi professional football or soccer for the Americans and that was incredibly important for me because it was outside of work, outside of family.

It was something I did just for me. I'm retired and getting a bit older and I've replaced that with focusing on exercise and making sure that I'm exercising a good number of times a week, but then also making sure that I'm giving myself head space inside of work to reflect on the things that are happening to me day to day. That usually takes the form of a 15 minute coffee in the morning or a 15 minute meditation in the afternoon. The other thing, you asked who. Something that's been very important for me in the last probably four years is really finding a strong network outside of work, but that is work related. It's not family, but it's...

I've been fortunate to have some great executive coaches in the last four years, and I've also been fortunate to have some great mentor outside of work and outside of the company because I think it's important that they're outside of your company that I can just go and talk to. Whether it's been a coach or a mentor, I can go to them and say, "Hey, I'd love to chat for 45 minutes. I've got this problem. I'd love your perspective on." I can go and in a very safe environment I can say, "Hey, here's the problem. This is how I'm approaching it or this is what I've done. What do you think," and very quickly I can get a thumbs up, thumbs sideways or thumbs down like what the fuck are you doing, but in a very safe environment because they're people outside of work.

I think finding my people in terms of coaches and mentors has been incredibly important for me to help you deal with the painful moments as a design leader because it is painful.

Carl: Yeah. I think what you just shared about having someone outside of the company, sometimes even outside of the realm of what you do, it helps because you can listen to them, because they're just listening to you explain a situation and you don't get your defense up right away. You're not like...

Alastair: Well, that's the thing as well. If I look back at one of my-

Carl: That's powerful stuff.

Alastair: ...mentors probably eight years ago now, seven or eight years ago, Beck and Simone actually, they were both not designed leaders. They were general managers, directors of businesses. They weren't designed leaders, but they've given me some quite incredible counsel over the years and some quite incredible feedback that's been incredibly important. It doesn't have to be a design leader that's giving you that feedback.

Carl: Yeah, that's absolutely right. Well, Alastair, thank you so much for spending time with us today. There's one thing I want to say before we go.

Alastair: Okay.

Carl: HipChat respect. I'm part of the alliance, sir. It feels like a rebel force right now. I'm going to tell you, but I've always loved HipChat.

Alastair: Thank you for having me on, Carl. Thank you for the feedback.

Carl: Fight the fight, man. fight it. You got it. You got it. everybody listening, thank you so much and we'll be back next week. all the best.

Image via Atlassian

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