The Counterintuitive Journey of Design Leaders

Some things in life follow a natural progression.

Before a baby can move, they cry and reach for what they want. Then they learn to crawl, then walk. Before you know it, you're chasing them through the house because they've snuck a snack cake from the pantry just two minutes before dinner is ready (true story).

Learning to ride a bike is similar: you start with training wheels, wobbling and trying not to fall. You keep practicing, you gain confidence, the training wheels come off, and soon you're riding effortlessly.

We often think a designer's career will work the same way. Start with basic design skills, work hard, and learn techniques. Eventually you'll be great at designing and you'll spend your days making masterpieces. Sounds simple, right?

But becoming a design leader goes beyond mastering design tools or polishing your work.

Before joining CōLab, I was a Motion Design Lead at Airbnb. In my final year there, I interviewed 33 of the most senior designers at the company. All the conversations were focused around one question:

“What does it mean to be a design lead?”

From my conversations with top designers, I learned about the unexpected paths of design leads. The journey includes learning how to lead, inspire, collaborate, communicate, and bring innovative thinking to the design process. Every story was unique, and each person had their own insights and special sauce. Let’s explore a few key themes that resonated through their responses.

Question your leadership norms, and find your own way

What does authentic leadership look like to you, when you dig under the surface? How do you want to lead?

Annie Wu, Product Design Lead at One Project

"Earlier in my career, I had this mental model of leadership that was about being loud and taking charge of things at the front of the room. However, that approach didn't always feel authentic to me. Now, I think about leadership in a way that is closer to servant leadership.

"There's an interesting quote that says the sign of a successful leader is when you bring a bunch of people together to accomplish something, and at the end, everyone feels ownership of the solution, like you all came to it together and it feels seamless and easy.

"This is how I think about leadership now—it's almost like enabling and supporting other people to get the work done."

Anna Sanguinsin, Staff Experience Designer at Airbnb

"I had this preconceived notion of what leaders in general should be, this idea that they're always kind of the leader of the pack. They're always vocal. They should be the first one to jump right in and answer the question in any meeting.

"And I think what I learned is that every single design lead has a unique perspective and a unique leadership style. The style that really resonated with me is that of quiet leaders. If you think about the pack, there's always that person in the front. But what about the people or the leaders at the back who are waiting for others? Who’s making sure everyone is on the journey with you, making sure that they're opening up pathways for others that set a team up for success?"

Salih: “I love what you said about a kind of leader who is in front and they're cutting through the jungle, they're creating a path. But then there's also the leaders in the middle who are helping each person get across the bridge, and there's a person at the very back of the line making sure that people in the back are keeping up, making sure that nobody is falling behind. You need all of those kinds of leadership.”

Anna: “When I think of leadership it’s definitely about people, not only the projects but the people. Taking care of your people.”

Stay grounded and flexible

Question how you wield your leadership. Are you making space for others to uniquely grow, or getting lost in the gravitas of a title?

Taido Nakajima, Pillar Design Lead, Ecosystem & Applied AI Lead at Webflow

"Don't let that title get to your head. I think that's the biggest thing. At the end of the day, we're all human. We're all people. Instead of thinking as a design lead, it's just always having a mindset as someone who can be a good role model for one another and someone who can be counted on."

Jamie Cristal Joaquin, Design Systems Manager at Airbnb

"Back in the day, I would approach things like a woodworker. I would just carve my ideal and make sure everything was smooth and sanded.

"But now as I’ve progressed in my career, I think I see myself more as a gardener. Just making sure that I'm nurturing the seeds and providing these ideas with the right environment. Making sure that they get enough nutrients, whether it's sunlight or water, it's just about making sure that they have room to organically grow the way they want and not necessarily me forcing them to do something that I want. For designers that are looking up to me or see me as a mentor, I'm not gonna force-fit them into my mold. I’d tell them what worked for me but would definitely make sure they have all the tools and assets that they need to make their own decisions."

Salih: "Did you know I was gonna ask you, and you were like, what kind of cool metaphor can I come up with?"

Jamie: "No, I'm pulling everything out of my ass right now."

Salih: "Because that's a really good one. And it applies not just to mentoring younger designers, but it applies to the arc of a project as well. You know, like you can try to fit that project in a box or you can see where it's gonna grow and be there to support."

Jamie: "Some projects will not see the light of day, right? Some seeds will never grow or bloom where they're planted, right? So you do everything you can to make sure that it lives to its potential.”

Master the art of alignment

At this level, sitting down pushing pixels and creating is tangential to the hard work of helping move an organization forward through advocacy and intention.

David Muro, Senior Staff Experience Designer at Airbnb

"Collaboration is about taking ownership and responsibility and just seeing it through and working with as many people as needed, to get it done. Moving beyond just your immediate team. How do you work with partners to make an impact and tackle these big ambiguous problems, everything firing on all cylinders to get the job done, to get something over the finish line?"

Jarrett Carr, Design Lead at Chime

"I look at it as a responsibility to challenge the thinking of the entire organization, right? Have an opinion about what the company needs, have an opinion about how people should be approaching certain problems or how the organization or individuals can change their behaviors to improve the lives of their people and the people they're producing a product for. And I think that's everyone's responsibility to some extent, but it becomes much easier and more comfortable in the position that design leaders are in right now. And that's outside of actually producing anything at all. The actual production side of it I think is 'tangential.'"

Connect the dots, and untie the knots

Navigating ambiguity and developing a holistic view becomes key to operating at a higher level.

Tiffany Ng, Product Designer at Airtable

"I find it to be more ambiguous problems or these knots that end up getting formed as you grow bigger and bigger as a company. Untying those knots or resolving those tends to be the main focus of problems that I solve. I feel like design leads have the opportunity to align everyone and decide on a path forward to resolve things that might not have a clear answer.”

Michael Lashford, Design Principal at CashApp

“The thing that's not in the brief or in the job description for a design lead is connecting dots. And that's not something that's easy to do when you're a younger designer because you're just trying to make the thing look good, trying to appease the managers, and also trying to have your own stamp on a thing. Your focus is a lot lower.

“If you're a design lead too focused on a flow, a shadow, or whatever minor detail you're fussing over, you're not leading as strongly as you could or should be for the work or the team. If I see someone on my team is frustrated or working slowly because maybe they have a personal issue, and if I'm not checking in with that person and having a true, honest heart-to-heart with them, which has nothing to do with design, then I'm not connecting the dots. Because that player on my team is not performing at their best due to being upset or sad or something like that. If you're not zooming out and taking in the whole holistic view of your world, industry, company, and team, and even down at the lowest level, the surface you're working on, you're not truly leading, and you're performing at a lower level.

“At least, that's my personal opinion. It's really, really hard to do. I'm not an expert at it. It just takes proactive thought and repetition to check yourself.”

The definition of “the work” changes

The move to design leadership shifts everything from your mindset to your goals to your approach to day-to-day work.

There were a lot of common themes that kept coming up that seemed important to the job of a high-functioning design lead. But no one said that being a design lead is about sitting down creating mind-blowing designs. No one mentioned Figma or Photoshop. In fact, they didn’t mention creating at all. Now, of course, each of these designers are experts at their craft and could dig into the pixels with the best of them. But why didn't that ever come up?

It’s because when you get good at the craft of design, the designing actually becomes secondary to everything else.

At CōLab, we work with startup founders every day. And after you talk with enough, you realize that most founders of any kind of business started out because they got really good at something. Sewing, baking, cooking, engineering, teaching — whatever it was, they developed a love and passion for it and eventually it led to them creating a business around it. Most of the time when they become the CEO of that business, they’re spending way less time doing the thing that got them in the game.

It’s no different for designers. Personally, over the years my time has shifted away from the thing I came in doing and my focus has definitely shifted from "How do I make this good?" to "Why will this matter to someone?" "Who will this impact inside and outside the company?" "Who do I need to collaborate with to make this better?" "How do I help all the relevant parties align at a decision?"

Younger designers might be reading this thinking “Ok so you’re telling me I’m spending all this time getting good at design just so I can stop designing?!?!”

Yes and no. The journey of a designer's career evolution from crafting intricate designs to becoming a design leader is a remarkable transformation. It’s not just a change in responsibilities but a profound shift in mindset. The insightful perspectives of the designers that I talked to show that being a design lead goes beyond the pixels and creative processes; it encompasses the art of leadership, collaboration, problem-solving, and driving meaningful change.

In the role of a design lead – where creativity meets strategy – it’s not enough to create beautiful designs. You have to make a lasting impact in whatever form that may come. It could mean facilitating team bonding, creating an environment where ideas flourish, or pulling people up who need support.

As designers get more seasoned and embrace this transition, they find themselves on a path of continuous growth and newfound wisdom, ultimately contributing to a more well-rounded version of creative excellence.

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Big thanks to my Airbnb fam who let me interview them. Adam Shutsa, Chaiporn (Be) Chanlimcharoen, Chip Davis, Annie Wu, Danny Spitzer-Cohn, Benjamin Evans, Andrea Limjoco, Doug Alves, David Muro, Jamie Cristal Joaquin, John Yum, Jarrett Car, Jonathan Rahmani, Juca Lopes, Lucia Ciccio, MK Loomis, Melissa Showalter, Olivia Batraski, Michael Navarro Lashford, Taido Nakajima, Tiffany Ng, Rachel Nash, Tuhin Kumar, Tracy Kuwatani, Rick Lee, Kimberly Hunt, Edwin de Jongh, Michael Austin Sui, Vibha Bamba, Peiyu Liu, Damjan Stankovic, Anna Saguinsin.