An interview with Alastair Simpson

Alastair Simpson is VP of Design at Dropbox and will be speaking on ‘Building a culture of craft’ at Leading Design London 2024 (6–7 November) at the Barbican Centre.

Alastair Simpson leads Dropbox’s Design team across Brand, Product Design, Writing, and Research, and played a key role in shaping the company’s Virtual-First approach to remote work. Prior to Dropbox, he was Head of Design at Atlassian for six years where he helped scale the design team from 20 to over 250 employees, a company from 900–5000 employees as well as through a successful IPO.

With experience spanning startups and large-scale companies across the US, UK, Europe, Australia, and South East Asia, Alastair focuses on using human-centred design to solve business challenges.

Ahead of his talk at Leading Design London, we caught up with Alastair to ask him about his approach to design leadership and the making of a culture of craft.

What would you say the top three character traits of an effective leader are?

There are many traits that I find critical to be an effective leader, but if I had to pick my top three, I would choose the ones that I personally aim to embody: openness, persistence and passion.

Firstly, openness and true transparency are key to creating and building trust within teams, which ultimately enables better relationships and better product building. Secondly, nothing great is won easily, which is why persistence is important to leading, and leading well. Leaders who consistently work hard and demonstrate perseverance will in turn, cultivate teams that do the same. And lastly, exemplify passion because people follow passionate people. As a leader, show that you care deeply about your work, your team, your personal life, and whatever else makes you feel fulfilled.

What is the greatest challenge you have faced as a leader?

One of the greatest challenges any leader will face is learning to scale oneself. At a certain point, the hard skills around leadership are mostly the same. But what differentiates leaders who can “cope with the scope” and scale growth is their ability to successfully scale themselves personally, not just professionally. As you grow in scope and responsibility, the magnitude of the decisions that you have to make is much larger and the impact is much wider. Therefore, being able to remain calm and poised due to the personal work being done, even in the most chaotic and pressurised of situations, is paramount.

To me, scaling myself and enabling myself to remain calm means many things including creating healthy boundaries, learning to switch off, becoming laser focused on prioritising my time against the most important problems, and building a team around me that enables me to be my best self. Scaling also means leaning into personal interests and figuring out what makes you tick, and making time to enjoy those things. It is impossible to give your best self to work, if you are not also enabling yourself to be your best self outside of work.

There is a lot of talk about the wider business value that design can have, why do you think that it’s important to focus back on the craft?

I believe that design must be a strong cross-functional partner to any and every cross-functional discipline in order to have company and product wide impact. We have to also be product tinkers as well as designers. However, as designers, our number one priority must be our design craft and building products that solve our customers’ problems, and also delight them in moments that matter. We can’t lose sight or focus on the main thing that we are accountable for. The more passion we pour into our craft and creating outcomes we love, the more pride we have in our work. This feeds into the flywheel of culture and enabling a care for craft in everything that our company does.

What do we mean when we talk about ‘craft’? Is that different from doing the job?

It’s important to get crystal clear on what we mean when we talk about craft. Craft is the combination of someone with great taste who also cares really deeply about what they are making. Having great taste comes from a recipe of many different things, including having deep knowledge of your subject matter from many different angles and having sustained precision and persistence in everything you do. I like to think of taste as the palette and toolbox that allows you to then craft your own outputs. Taste is what you have to work with, craft is what you’re able to do with it.

For product design, craft is about how the product feels to use — it’s the attention to detail, the technical skill, and the care and commitment to building a high-quality product.

What do you think causes designers to lose their focus on the craft and what’s your number one tip for avoiding this?

Losing focus on craft is about the loss of intention. In the last decade of my life, I’ve been leaning into the notion of being hyper-intentional with everything that I choose to do and spend my time on. I don’t believe people try to be unintentional, but the reality is life happens quickly and we lose focus on our intentions.

Here’s a common scenario: it’s December 31st, the ball is dropping, and as the seconds tick down, you’re filled with hope, excitement and the best intentions for the year ahead. You make a promise to yourself, a New Year’s resolution, that this year will be different. You’re determined and ready to take it on. But, as we all know, the reality often looks quite different by the time February rolls around. In fact, studies show that 88% of people who set New Year’s resolutions fail them within the first two weeks. Data from the social fitness platform Strava has found that by January 12th, most fitness kicks start to wane.

Relating this to my role as a design leader, every designer following along knows we all start out with the best intentions. It’s like making a New Year’s resolution — we start with the best of intentions:

• To craft with excellence
• To simplify everything that we make
• To be incredibly customer-centric
• To deliver only the best user experiences

But somewhere along the way, things start to slip:

• We don’t speak to customers as frequently as we should
• Design critiques shift from critique to seeking consensus
• Hiring and onboarding take a backseat to all the things going on around you at work
• We make wrong compromises on design choices, because we don’t have the time of passion to have really hard conversations to get the right outcome

Why is it that our best intentions can so easily unravel? As I think about designing with intention, it’s my opinion that staying focused on our intentions means having the stamina and great foundational design habits to rinse and repeat. When things veer off track, which they undoubtedly will at some point, we have the fortitude to refocus on the fundamentals and not be distracted by some new and novel idea. The foundations of our practice are time tested and we should honour them by giving them the focus they deserve.

And finally, what are you currently listening to, reading or watching?

Reading: Breathe By James Nestor. This has really made me rethink how to do such a natural thing: breathing.
Listening: https://soundcloud.com/alanstairs, and a couple of my favourites are Maribou State Essential mix and some friends of mine.

We are delighted to have Alastair speak about ‘Building a culture of craft’ at Leading Design London 2024 (6–7 November).

Leading Design is brought to you by Clearleft, a strategic design consultancy based in the UK. We work with global brands to design and redesign products and services, bring strategic clarity, and transform digital culture.