Paths to Design Leadership

This talk explores the different ways a designer might grow in their career via their craft, team, and strategy through concrete examples of job roles, activities, impact, and examples of profiles. Insights will be shared into how the audience might carve their own path to leadership at their current company by assessing design maturity, building support, and executing strategy.

Hosted Hang Le: Design Leader & Researcher | Head of Design at Eppo

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Prefer to read? Below is an automated transcript that has been cleaned up by AI. Apologies for any errors!

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Welcome to "Paths to Design Leadership" hosted by Hang Le. Hang is a design leader with extensive experience in B2B software. She’s led teams at Dropbox, Earnin, and is currently the Head of Design at Eppo. She'll definitely talk more about her background when I hand it over to her, but before we do that, I just want to tell you a little bit about Designlab and introduce who we are.

I’m really excited to have all of you here today, whether you're from our community or outside of it. A little bit about Designlab: We are an online education platform focusing exclusively on digital design. Our education model combines online, project-based learning with expert live mentorship. Over 20,000 students have taken our classes, and we have programs for those transitioning into design careers, working designers, and design teams. We also offer custom team training, and we have some courses now for folks who may want to learn UX/UI but aren’t necessarily designers. So, there’s a little bit of something for everyone, whether you’re a career changer or just looking to upskill.

One more thing I want to mention is that we’re offering all attendees of today’s event a $100 discount code for our courses. You can apply it to any course of your choice. All you need to do is enter the code on the screen at checkout, and it will be automatically applied. I’ll also drop a link in the chat with the coupon attached, which will take you directly to our courses page. There you can check out all the different courses we offer for designers, like our AI for Visual Design course, our advanced accessibility and usability course, some programming around Figma, and of course, our pilot program UX Academy, which is more geared toward career changers.

I'll share some ways to get in touch with our team if you’d like to ask questions or just want to reach out and say hi. With that, I’m going to hand it over to our speaker, Hang Le, who I’ve already introduced. I’ll get out of your way now. Hang, you can take it from here!

Hang Le:

Thank you, Emilyann! Hi, everybody. I hope you’re having a good start or end of your day, depending on where you are. I’m really happy to talk about design leadership today. I’ve written a lot about this topic before, so when I was approached by the team at Designlab to do a talk, I thought, "Why not?"

I’m Vietnamese, born and raised there, and I moved to the U.S. around 2010. "Xin chào" is how you say "hi" in Vietnamese. I’ve been working in digital design since 2008, and I’ve had a pretty good career in that time. I’ve been head of design three times. In 2018, I was head of design at Earnin, a fintech startup, where I built the design team from 5 to 15 people. Then, I was recruited by Dropbox, where I led the Document Workflows team, which was composed of all the acquired startups. That team had about 20 people. Now, I’ve transitioned back to a smaller team at Eppo, where I head the design team of three.

So, I think my perspective is unique because I’ve led teams of different sizes at different stages of company growth. That’s why today I want to talk about three main things:

1. What is design leadership?
2. How design leadership changes depending on the size of the company and the team.
3. How to carve your own path, especially in challenging times like these.

Let’s start with what design leadership is.

In the simplest terms, leadership is the ability to guide or influence others. In design, I think of leadership as having three dimensions:

1. Guiding the quality of the work.
2. Guiding the strategy of the company.
3. Guiding the team that produces the work.

Let’s break those down a bit.

First, guiding the company’s strategy. This means defining the company vision and the design strategy, influencing the roadmap, and uncovering insights that might not be immediately obvious. When I mentor people, one of the common questions I get is: "What’s the difference between a company vision and a design strategy?" A company vision is about why the company exists and the impact it wants to make in the world. It has nothing to do with how design is done. The vision is more about understanding why the company is needed and what the market response is to that vision.

On the other hand, design strategy is about making choices. It’s about deciding what we want to do and how to do it, based on the insights and data we get from the company’s vision and business health. It’s about figuring out how design can best contribute to achieving that broader company vision. Sometimes these distinctions can be subtle, but I think it’s important to understand that the design strategy is really about delivering value and figuring out how design can help provide that value to the users and the business.

A good example of this kind of design leadership is someone like Kat Mo, who I worked with at Dropbox. She was a staff product designer, which is sometimes called a principal designer. She didn’t manage anyone, but her responsibilities were at the level of a director. She worked on cross-product strategies, helping users navigate between Dropbox’s different products. That kind of work is crucial to company strategy, and even though she wasn’t managing a team, she was leading from a strategic design perspective.

Second, let’s talk about guiding the quality of the work. This is the more traditional side of design leadership. It involves ensuring that the solutions we’re building are high-quality and solve the problems they’re meant to address. Activities here include leading design critiques, creating and maintaining design systems, and shipping features that are polished and intuitive. A good example of this is Triam, who manages the IBM Carbon design system. Carbon is an open-source design system used internally at IBM and by external developers. Triam has been a design leader for years, and she’s focused on ensuring the highest quality across IBM’s design system.

Finally, the third dimension is guiding the team. This is what most people think of when they talk about design management. It includes things like staffing, performance reviews, operations planning, and team development. It’s about making sure the team is working efficiently, on the right things, and that they have the support and resources they need to be successful.

One of the key decisions for a design leader is determining the best structure for the team, depending on the company’s goals. There are different ways to organize a design team, and they evolve over time. For example, Peter Merholz has a great model in his book "Org Design for Design Orgs" that shows how teams can be structured either horizontally, with design operations, UX research, and design all reporting to the same leader, or vertically, where design teams are embedded within specific business units.

So, to summarize, design leadership involves these three key areas:

1. Strategy: Defining and guiding the company vision and design strategy.
2. Quality: Ensuring the design work is solving the right problems and is of the highest quality.
3. Team: Managing the team, operations, and resources to support great design work.

Now let’s dive into how design leadership changes depending on the size of the company.

The complexity of design leadership increases as the size of the company grows. The two key factors that drive this complexity are scale and context.

1. Scale: As a company grows, the risks associated with decision-making increase. For example, the larger the company and the more revenue at stake, the more costly it is if you make the wrong decision. Design leaders at large companies need to consider these risks when making choices.
2. Context: As the company evolves, you’ll have more people involved in decision-making and more perspectives to align. You have to manage different stakeholders, opinions, and priorities. Aligning all these different perspectives becomes part of the design leader’s role.

A helpful way to think about this is to look at the roles of a design leader at different levels of scale. This framework comes from Peter Merholz, and it’s useful for understanding how your activities as a design leader shift as the company grows.

There are three primary roles for a design leader:

1. Coach: You’re coaching your team, helping them grow their skills and improve their performance.
2. Diplomat: You’re acting as a diplomat with your peers in other functions, like product and engineering, to ensure alignment across departments.
3. Advocate: You’re advocating for design and the user to upper management, ensuring that design has a seat at the decision-making table.

As the team grows, your time spent in these roles shifts. For example, when I was leading a small design team of three at Eppo, most of my time was spent coaching the team and occasionally managing up and across. However, when I was at Dropbox leading a larger team of 20, my time was spent more on aligning horizontally with product and engineering, less on coaching directly, because I had design managers who took on that role.

This shift is why many design leaders feel like they’re no longer "doing design" when they move into leadership roles at larger companies. Your time and attention move away from hands-on design work and into growing the culture of the company and ensuring that the team’s strategy aligns with the company’s goals. In larger organizations, you’re spending more time on high-level decisions and less time on the day-to-day design details.

The Role of Scale and Complexity
As companies grow, the complexity of design leadership increases. The larger the organization, the more context and alignment are required for decision-making. For example, in a small team, you may have all the context you need to make a decision because you're directly involved in everything. But in a larger team, there’s more complexity, and you need to gather context from others to make informed decisions.

A great model to think about is that, as a design leader, you’re responsible for three areas:

1. Coaching your team.
2. Diplomacy with your peers at the same level.
3. Advocacy for design with senior leadership.

The balance of your time in these areas shifts as the company grows. For example, in a small company, most of your time might be spent coaching your team. But in a larger company, much more time is spent on diplomacy—aligning across functions like product and engineering—and advocating for design at the executive level.

At Dropbox, for example, most of my time as a design director was spent working horizontally with product and engineering, aligning their goals with our design strategy. Meanwhile, my design managers took on more of the direct coaching with the design team.

Carving Your Own Path in Design Leadership
Now, I want to talk about how to carve your own path as a design leader. This is especially important in times of uncertainty, like we’re seeing now.

The key takeaway here is that, in order to be recognized as a leader, you need to already be doing the work of a leader before anyone officially gives you that title or recognition. You have to show leadership in your actions, rather than waiting for someone to tell you you’re ready.

Especially in difficult times like these, when companies are laying off designers, it’s easy to feel insecure about job stability. However, I believe that challenging times present opportunities for those who can step up and fill gaps in their organization.

So how do you carve your own path as a design leader?

I believe there are three important steps:

1. Understand your company’s most pressing problems: You need to proactively identify what issues are critical for your company. It’s your job to spot these and help solve them.
2. Be the agent of change: Don’t wait for someone else to fix the problem. Step up and lead the charge for change.
3. Influence others to buy into your vision: Once you’ve identified a problem and a potential solution, you need to get others on board so that you can create real impact.

Let’s break these down.

Understanding your company’s most pressing problems
The easiest way to find out what your company’s biggest challenges are is to use your one-on-one time with your manager or cross-functional partners to ask the right questions. Ask about the company’s strategy, the quality of the product, and the state of the team. If you don’t have regular one-on-ones with the leaders in your company, I strongly encourage you to set them up. Then ask: What are your most pressing problems in strategy, quality, or team? You’ll likely get answers that point you in the right direction.

Once you have that information, the next question is: How can you help take something off their plate? It might be something like improving a process, shipping a feature faster, or tackling a quality problem. For example, quality problems might include questions like: Are we solving the right problems? Are our features high quality? Are users happy with what we’ve shipped, or do they keep complaining about bugs or usability issues? Are customers actually adopting the features we’re shipping? These are signs that the company has a quality issue.

On the strategy side, signs of problems might include things like: Can you clearly name the company’s most important initiative for the next 12 months? If you can’t, that might be a sign the strategy isn’t well communicated. Or you might see a misalignment between the marketing message and the actual product experience, which is a strategy problem.

When it comes to team issues, you might ask questions like: Are people aligned with the company vision? Are projects properly staffed, or is work being assigned without proper planning? Does the team have the skills it needs to keep up with the complexity of the work? For example, if it takes two months to change a simple text on the product, that’s probably a sign of a process or people problem.

Examples of Solving Problems
Here are a couple of examples from my own career.

When I first joined Eppo, I conducted a simple audit using a usability scale and customer reviews. I identified areas where I thought we could improve—things like product management pages and simplifying the information architecture. This allowed me to start contributing at a higher level early on and establish myself as someone thinking about the bigger picture.

Another example is a “State of Design” write-up I do every six months or so. I step back and assess where we are in terms of design quality, strategy, and team. I then propose what I think we should focus on next. For example, I might suggest increasing our product success rate or redesigning a specific part of the experience. These kinds of audits show that you’re thinking strategically and not just focused on execution.

Being the Agent of Change
The second step is being the change. Once you’ve identified a problem, it’s not enough to point it out—you need to take action. In my experience, the biggest gap between people who want to lead and those who actually lead is the willingness to step up and make a change.

As designers, we’re problem solvers. The same design thinking you use to solve product problems can be applied at the strategy level. Gather data, identify the problem, frame it clearly, and propose solutions.

For example, if you’ve identified a product quality issue, you can run surveys, talk to sales and support, and pinpoint the top areas for improvement. Then you can frame a solution and present it to leadership. Even if the change you want to make seems small, it's the action that sets you apart as a leader.

Tie Your Solutions to Business Outcomes
One of the most important things to remember is that your proposed changes need to be tied to the business. It’s not just about making changes for design’s sake—it’s about solving problems that impact the bottom line.

There are two primary ways to tie your work to business outcomes:

1. Saving money: For example, improving the onboarding process reduces the need for customer support, which saves money. Decreasing churn is another way to save money—if you reduce churn, you avoid the high cost of acquiring new customers.
2. Making money: For example, improving product quality leads to happier customers, who are more likely to recommend the product to others. Increased adoption of key features means customers are getting more value from your product, which helps with retention.

For instance, if you run a quality initiative that reduces the amount of rework or increases feature adoption, you’re directly contributing to business growth.

Influencing Others
The third and final step in carving your path as a leader is influencing others. Even if you’ve identified the problem and proposed a solution, you’ll need buy-in from others in the organization to execute and create real impact.

When you’re trying to influence others, it’s helpful to create what I call a relationship map. This map should answer three key questions:

1. Who do you need feedback and support from?
2. Who has the trust of the organization, and do they trust you?
3. Who is likely to object to the changes you want to make, and how can you convince them?

One of the lessons I learned when I moved into larger organizations is that power and trust are not always aligned. There are people with a lot of power but not much trust in the organization, and there are people who don’t hold a lot of power but are highly trusted by everyone. The key to gaining influence is focusing on those people who have high trust. They can support your initiatives and help you get others on board.

As a design leader, you’re balancing three relationships: coaching your team, working horizontally with your peers (product, engineering, etc.), and advocating to leadership. Think about who you need to align with in each of these areas to successfully influence the changes you want to make.

The most important question to answer when you’re influencing someone is: Why should they care? To be honest, most people outside of design don’t care about things like design systems or critique processes. But they do care about things like consistency in the customer experience or making sure the product meets business goals. You need to frame your initiatives in terms of why they matter to the company and the person you’re talking to.

Once you’ve established that, be sure to have a clear ask. What do you need from them—feedback, support, or just a thumbs up? Make your request clear, and then proactively solve the problem. Afterward, be sure to document the results so you can show the impact you’ve made.

Wrapping up
One quote that I love is: “Luck is when preparation meets opportunity.” I truly believe that the best thing you can do for yourself is to prepare. Even if you’re not immediately promoted or recognized, having a solid plan, demonstrating leadership, and building up your experience will put you in a strong position for the future.

If you’ve been carving your own path and showing that you’re already leading, then when opportunities arise—whether it’s for a promotion or something else—you’ll be ready. Preparation is the key to unlocking future leadership roles, regardless of the immediate outcome.

That’s what I’ll leave you with today. Thank you for listening! I’m happy to take questions now.

Q&A Session

Emilyann: Amazing! Thank you so much, Hang, for your time today. We have a few questions from the audience.

Perna asks: Do you think studying design management or a related course can give someone a leg up on the corporate ladder? Many people think these skills can be gained through professional experience. Can you share your thoughts on this?

Hang: Yes and no. Most of the time, companies promote people into leadership roles not because they’ve taken a specific course, but because they’ve demonstrated they can do the job. That said, if you feel like you need more information or skills, a design management course can be useful, but only if it has a strong application side. It’s not enough to just learn theory—you need to show that you can apply what you’ve learned.

Emilyann: Great, thank you. ML asks: Hi, Hang, what are the top three things you wish you knew before you stepped into design leadership?

Hang: Hmm, good question! Let me try to list three.

1. First, I wish I knew how misunderstood design leadership can be. It's often misunderstood by the people we work with, who think design is just about making things look nice, but it’s also misunderstood within the design community. There’s no consensus on what design leadership actually is, which makes it hard to convince others of its importance.
2. Second, I wish I had realized that, as a design leader, you’ll spend less time on the actual design work. Your job is to guide the team and company, not to do the day-to-day design work yourself. Sometimes, what pushes the company forward isn’t traditional design work at all.
3. Lastly, I’d say it’s important to understand whether you’re working in a company where design is truly a differentiation factor. If your company’s success hinges on good design, then design leadership will be critical. But if design is seen as a commodity, it’s harder to lead effectively because design isn’t viewed as a key driver of success.

Emilyann: Thanks, Hang. Next question comes from Cynthia: How do you develop leadership skills on your team and help people transition from hands-on roles to more strategic ones?

Hang: There are two main parts to this. The first is creating an environment where people can grow—this might mean offering mentorship or making leadership opportunities available, like leading small projects. The second part is education and exposure. Encourage your team to attend leadership workshops, read relevant books, or take courses. But the most important thing is practice. You need to give people the opportunity to take on leadership tasks and see how they handle them.

Emilyann: Awesome, thank you! Emma asks: What’s the best way to show your leadership skills on a resume or portfolio?

Hang: On a resume, it’s important to show your impact rather than just listing the tasks you completed. For example, don’t just say, "I led three projects." Instead, talk about how those projects made a difference to the business. Show that you were thinking strategically, solving important problems, and driving outcomes.

For portfolios, if you haven’t had a formal leadership role yet, you can still demonstrate leadership by sharing a case study where you identified a problem and proposed a strategic solution. You don’t have to be in a leadership position to think and act like a leader. Include your thought process and how you would approach solving larger organizational challenges.

Emilyann: Great advice! Last question from Allison: What should your portfolio demonstrate to get hired as a principal or staff designer?

Hang: It depends on the company you’re interviewing for. Larger companies like Facebook or Google are usually looking for strong visual design and design systems work. If you’re applying to a startup, they’ll want to see that you can think strategically and move quickly with limited data.

I recommend tailoring your portfolio to the specific company. When I was job-hunting, I had three different versions of my portfolio to match the type of company I was applying to. For big companies, they’ll focus on your craft—how polished and detailed your work is, and whether you can handle complex projects. For startups, they’ll be more interested in your ability to think big and move fast.

Emilyann: Thank you so much, Hang, for all your insightful answers, and thank you to the audience for the great questions! We’ll have a recording of this session available soon, and we’ll email it out along with a link to our YouTube channel.

Before we wrap up, I just want to share that discount code again for anyone interested in our courses. The $100 discount will be automatically applied if you use the link. Thank you, Hang, and thank you everyone for joining us today!

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