A Career in Design leadership: In Conversation with Matt Herlihey

A Career in Design leadership: In Conversation with Matt Herlihey

A Career in Design leadership: In Conversation with Matt Herlihey

I recently had the privilege of having a conversation with a seasoned design leader at Shopify, Matthew Herlihey. Our discussion spanned the practicalities of their day-to-day responsibilities, the journey that shaped their career, and their vision for the future of design leadership.

The Present: A Day in the Life of a Design Leader

What leadership means as an Individual Contributor

As a product design leader, one represents the discipline at the highest level of the product, collaborating with other leaders to decide on what projects need investment in order to decide where design can have the most impact.

“I bring my UX experience to the table with my product manager counterpart, my development counterparts and management counterparts. And together the four of us decide what projects are worth putting our time into, what investments we want to make in our team and how we want to support our team to grow.”

They guide and enable their teams to succeed by providing resources, helping the team communicate with stakeholders, helping to unblock problems, and sometimes even getting their hands dirty in design work, coming up with solutions that would, that would give Shopify the best solution for what they’re trying to solve from a very high level.

💡 In a nutshell, leadership as an IC means a mix of mentorship – helping their teams succeed and grow – while having their finger on the pulse of the product so they can keep the team moving forward.

Day-to-day responsibilities

Matt described some of the practicalities that go into making this magic happen. A significant portion of the day involves

  • Context gathering : Staying updated on project statuses, blockers, and alignment across teams.

  • Mentorship : Providing feedback, and facilitating design reviews through one-on-ones, group sessions, and ad-hoc discussions.

”It's a bit of like some of the stuff that a manager would do, but because I'm not their manager, it offers up some flexibility in the things we can discuss and then we have larger group things where we'll review as a design group just to get fresh eyes on work”

💡 Leadership in product design is as much about guiding the team and the project as it is about maintaining a high level of involvement in the design process itself.


The Past: Building the Skills of a Design Leader

Building a strong-foundation in user-centered design

The path to becoming a design leader is often winding, filled with experiences that shape and hone one’s skills. Matt’s experience comes from his work in industrial design which lead him to his roles in Shopify as a Product Designer.

Matt believes that the specific design tools used are not as important as having a strong foundation in user-centered design and problem-solving skills. He values being a generalist designer who can handle various aspects of the design process, from research to prototyping, rather than specializing in a specific area.

Differentiating levels of experience in design

”A junior designer is much more likely to be successful with a project that is going to be in the details, while a senior crafter is going to have to think more holistically about a problem.”

  • A senior crafter can work autonomously, think holistically about problems and their broader impact, and move between high-level and detailed work.

  • They excel at collaboration, mentorship, and most importantly, asking insightful questions to guide problem-solving rather than providing solutions directly.

💡 What differentiates a senior from a junior designer? A senior-level crafter, above all, knows to ask the right questions to get to the bottom of a problem

How to develop leadership skills
  1. Observing and learning from effective leaders

  2. Develop confidence in your craft and your position as designer. It enables you to take the time to absorb problems, consider different solutions, and determine if action is truly needed.

  3. Thinking at a higher level, and avoiding impulsive decisions, for example, senior crafters may take user feedback a bit differently:

    “If users are asking for a feature or complaining about something, the impulse is to just make that thing for them. But if you have a good sense of the area or a good sense of the problem, you can then take a step back and be like… well, the thing they're asking for isn't actually the thing we need to build. Actually like the problem is actually something else, something bigger.”

On Handling Decision Making, Conflicts and Disagreements

“And then at the end of the day, if you're in the leadership role, you have to have those hard conversations sometimes.”

  1. Take a step back and do not feel pressured to make a decision immediately when there is conflict or an impasse.

  2. Lean on other team members and have discussions to gain different perspectives before making a critical decision.

  3. Be honest, communicate well early on, and try not to withhold information when dealing with conflicts.


The Future: A Vision for Leadership and Design

Building a safe and collaborative team culture

“Good leadership for the group … means putting things in place that let people get to know each other and understand that everyone has good intentions and everyone is actually a nice person outside of work”

Matt shared that while he is averse to conflict in personal life, he don't see disagreements at work as conflict because the environment encourages debating ideas and speaking up.

It is important to building trust within the team and create opportunities for team members to get to know each other and understand everyone's good intentions.

💡 Creating a team culture for the future means assuming positive intent from the top down and creating a safe space for open discussions.

Evaluating company culture during job search

When I asked how how a person might evaluate a company’s culture before they join it, Matt suggested treating the interview process as a two-way evaluation, where candidates should assess the company's leadership, team-building processes, decision-making approaches, and hiring values.

“You are just as much interviewing them as they're interviewing you.”

💡 Ask about how a company holds people accountable, handles performance reviews, and deals with problematic behavior to gauge if the culture aligns with one's values.


Conclusion: My Personal Takeaway on Leadership

My conversation with Matt highlighted that there isn’t a single “right way” to lead—true leadership is about bringing your unique strengths to the team and enabling them to succeed in their own ways. In many ways, the seeds of effective design leadership come directly from the principles of design thinking. Just as design thinking encourages empathy, collaboration, and iteration, design leadership is about creating environments where team members feel safe to explore ideas, share challenges, and learn from one another.

Reflecting on Matt’s insights, I’m inspired to pursue a leadership style that nurtures connection, trust, and continuous learning, building a team that feels valued, motivated, and driven to create impactful work.