Leadership spotlight: Andy Healey, Shopify

When did you start thinking about yourself as a leader?

“It depends on what you mean when you say ‘leader.’ You can be a leader for your team, or you can also be a ‘thought leader.’ This isn’t a great term, so let’s use ‘subject matter expert.’ Before I started at Shopify, I was trying to be more of a subject matter expert by writing blog posts and contributing to a book about UX writing. When I joined Shopify, I was encouraged to do more of that kind of thing, so I spoke at conferences like Confab, internal conferences, and meetups. But I never thought of myself as a people leader.”

Why is that?

“I’m very much an introvert and have always been very happy working fairly independently. I had just never had an inclination towards people management as it seemed some way out of my comfort zone. After a year at Shopify, my lead moved to a different team, and then a year later my second lead did the same. I was the most senior person on a fairly small team, and none of us were relishing onboarding an external manager. So I thought it could make more sense for me to step up and take on that role. So I kind of took one for the team.”

And how long did it take you to make that decision from, “Maybe I should do this” to, “I’m doing this”?

“Literally probably a day.”

That’s super different from my journey. It took me about six months to make that decision.

“The process of moving into leadership isn’t immediate at Shopify; there’s a transition period that takes place over a number of months. But having another lead leave was the catalyst for me and I made the decision quickly.”

And you lead a team of UX professionals, not just content people, right?

“Yes, product designers and content designers.”

And you’d never led a team of just content professionals before?

“No. I’d never led anyone before!”

Tell me about that.

“Shopify has a history of promoting content people to UX roles. When I first joined, I was interviewed by Amy Thibodeau who was a content manager at the time. Seven months later she was a UX Director. And Alaine Mackenzie, who was Shopify’s first content designer, is also now a UX Director. This is because Shopify doesn’t make a big distinction between product design and content design; they’re super-intertwined. So, for example, you’ll see in UX reviews both the product designer and content designer talking about what’s being shown. And as a content designer, I’d sometimes work on projects as the sole UX person, especially when we were building information architecture-heavy features.”

Content design at its core is a specialization of product design. We’re all driven by creating the best experience.

How did that work being the only UX professional on a project?

“I worked the same way a designer would, using tools such as Figma, the same processes, and so on. Content design at its core is a specialization of product design. We’re all driven by creating the best experience. The only real difference was that I wasn’t a power-user of the design tools, and if I wanted to do something in Figma it would take me ten times longer than a designer.”?

Have you ever wondered what it would be like to lead a team solely made up of content designers?

“Yeah, for sure, content is my background after all. After my first team, I then had the opportunity to build a team from scratch. We didn’t have an opening for a content designer immediately, so I took on the role of stand-in content designer for a while and got back to my roots of content creation, rationale docs, and so on. And I had a great time getting closer to content again, I really enjoyed digging into the words the way I used to.

Focusing on content pushes you in one way; working with product designers has pushed me and helped me to grow in different ways. I feel super lucky that I had the space and the trust at Shopify to lead folks from a different discipline.”

I should have been kinder to myself. We all should.?

It sounds like you got a lot of satisfaction from digging into the work. Did you shift your idea of where you find satisfaction and recognition when you moved to leadership?

“To be honest, the first year I moved into a lead role felt like a perfect storm of chaos (laughs).?

Right after I took on the lead role, my product area, Checkout, was put on a new high-priority, high-visibility mission. Then, of course, Covid and lockdowns and working from home forever and the ‘new now’ happened. So I spent a year not really thinking about personal satisfaction from work. I wasn’t looking for any ‘feel-good’ vibes from it. Sometimes you’ll get positive feedback from peers, but I wasn’t actually looking for that sort of thing. I should have been kinder to myself. We all should.?

There were times where I thought about going back to being an independent contributor (“IC”) because in those moments it felt like it would be easier than leading a team. It was more in my comfort zone.”

Why is being a leader harder than being an IC?

“I don’t know if it’s necessarily harder, though it has certainly felt it at times; there are just different areas of focus. For me, as an IC, you tend to be focused on the project or the features. You get to go really deep and specialize and do deep work on difficult things.

As a manager, you’re spread more broadly, so you need to get accustomed to switching context. You need to represent UX at a leadership level with product and engineering. And I’m doing that with folks who are way more technical than I am. There’s broader UX vision and strategy to think about, and alignment across the company. Hiring takes a lot of time, and most importantly you need to support your team and ensure they’re set up for success.

There were a lot of new skills to pick up—you’re basically starting a new career. Shopify has a few internal training courses for new leads, so that was super-helpful, not just for the teachings, but also to be there with other new leads who were trying to figure it all out.”

I’m in a similar situation myself, where I’m managing individuals, building a team from scratch, developing strategies, looking at planning, and developing relationships across and up. How do you manage all of that?

“You know, in the last couple of years I’ve said to my lead a few times, ‘I feel like I’m doing several jobs not particularly well.’ But looking back, there’s a degree of spinning plates, and you learn where and when to give your attention. As a lead you don’t always get to go into the weeds how you might like. You need to be more high-level and strategic, and this takes some getting used to.

Prior to building my current team, I’d developed relationships with my leadership peers. And I worked alongside our designers to make sure that UX was represented well. So when I then had to build the new team, I’d already established trusting relationships and we were speaking the same language. I could almost afford to de-emphasize that side of things a little, run over here to build a team and start the hiring plate spinning, then run back and get the product and strategy plates spinning again. But now that I have a team, I’m able to hand over so many things, like mentoring and creating processes, and I can be way more focused on all those leadership things you talked about. Though as any lead will testify, there’s always going to be a degree of plate spinning.”

I’ve heard that leaders tend to focus on people, product, or process first. What do you focus on?

“For me, if you get the people and the product parts right, then the process naturally follows. Process is everyone’s responsibility, not just the leads, and my team will often know much better than me what process works best. Maybe that isn’t the case for teams with fewer senior members, but our team has the right mix for it to be an effective way of working. As for product or people, well, that isn’t fixed —as the team shifts, I shift from being product-focused to people-focused. Right now my team is in a pretty solid place, having just added two very senior product and content designers, bringing us to a total of seven.?

My first year, my focus was probably product 80% and the team 20%. As I built a new team, the first six months of this year was 85% people and product 15%, and now it’s swinging again to product 60% and team 40%.”

It sounds like when you think about people, you’re looking at organizational design. Is that accurate?

"I think that’s a primary piece. And then there’s a whole lot of detail that goes into that, like individuals’ career growth, or how they’re feeling on any given day. They’re the molecular pieces of organizational design. I spend every Tuesday doing one-on-ones with my team. I have six or seven, and it can be tiring, but there’s value in having that time with everyone. I spend a lot of time working on personal goals with my team. I make sure they’re aware of any training courses that would be relevant to them, etc.

I want them to be highly motivated and enjoy the work they’re doing, to see that they have opportunities for amazing growth in the same way that I was able to grow in ways at Shopify that I didn’t expect. This is why I spend so much time on the hiring process—the time spent there means that when folks join, I have a high level of trust in them to be both independently minded, but also integral team members. Because the most important thing for any lead is to do everything you can to set each member of your team up for success.”

I love how the team all bring different strengths to the table and help each other grow —it’s so cool to watch.

Do you do anything you might consider mentoring for your team?

“Yes, but it might not be easily identifiable as such (laughs). I spend time helping them understand how things work organizationally at Shopify. Who to speak to about what. How to approach and work with different teams. When and how to give different types of feedback. I’ve been at Shopify for around four years, and over 80% of the company joined after me, so my depth of organizational knowledge is great to share with the team.

I’ll also spend a lot of time before UX and product reviews helping them to define their stories. I find this is a part of many designers' toolkits that often gets overlooked. I actually presented at a meetup recently with my friend and Shopify alumni Ryan Bigge on storytelling for designers. We’re hoping to do more of that in 2022, with any luck IRL (“in real life”). More recently I’ve started to hand over the craft mentorship side of things to the more senior members of the team, and honestly, it’s been amazing, they’re really running with it. I love how the team all bring different strengths to the table and help each other grow —it’s so cool to watch.”

I’ve had a lot of managers over the years, some of them great, some of them not. And the two defining characteristics of my favorite managers, the roles where I had most success, were that, one, they gave me the space to succeed or fail, whilst being there to support and guide, and, two,?we had transparent relationships and enjoyed talking with each other.

I want to get back to the idea of leadership and what it means to you. Have you thought about what kind of leader you are?

“I’ve thought about it some. I’m a strong believer in both transparency and empowerment, as that’s just my natural personality. I’d rather give people as much information as they can handle so they can make their own decisions and have the power to take action.?I’ve had a lot of managers over the years, some of them great, some of them not. And the two defining characteristics of my favorite managers, the roles where I had most success, were that, one, they gave me the space to succeed or fail, whilst being there to support and guide, and, two,?we had transparent relationships and enjoyed talking with each other.

Now that I have this full team, I’m able to empower them to identify ‘here are things that need to be prioritized’ and ‘here are the things I need to think about.’ That lets them do their best work and take ownership of things. And when they do that, they become a high-performing team, which lets me work more on strategic-level thinking and future vision.”?

Do you have advice for those thinking about figuring out the kind of leaders they are?

“Make sure you get feedback from your team and from your peers. It’s encouraged at Shopify for everybody to do this at least every six months. Personally, I sometimes struggle at understanding how people perceive me, and I think a lot of people aren’t great at that. So getting feedback is essential to understand how you show up to other people.”?

Thanks so much, Andy!

“I never get to do this kind of thing. It’s been fun, thank you!”