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Want to Lead in Design? Kevin Flores Says Start Here.

Want to Lead in Design? Kevin Flores Says Start Here.

Nonlinear paths, decisive leadership, and why storytelling is your secret weapon.

Justin Lokitz
May 17, 2025

❝

Your ‘big break’ usually comes from someone you helped three years ago.

Kevin Flores

As long as I can remember, I’ve been asked (and have asked) questions about design and product leadership. What makes a great leader? What’s valued more: breadth or depth of experience? What are the bounds (and intersections) of design (and product)? And…what’s the “typical” path to leadership, etc., etc., etc.?

This is why I was so excited to speak with Kevin Flores, a multi-time design and product leader, who’s led teams at huge companies like LinkedIn, Verizon, and 23andMe, and has also cofounded startups and studios in between, at least one with a big-time celebrity ;-). Kevin not only answered these questions, but he did so with the calm clarity of someone who has experienced it all.

Given his wealth of knowledge and breadth of experience, bookended by his love of teaching, mentoring, and giving back, it only makes sense that Kevin, along with his wife, Jeanine Flores, who is also a design leader and ranked faculty at Mission College, recently coauthored and published the Design Career Handbook, an indispensable guide to designing your own design career.

In my conversation, Kevin didn’t offer clichés—he offered clarity. The kind of clarity that only comes from navigating ambiguity for 25+ years.

So, what does it really take to grow into a confident, strategic design leader today? Read on for my main takeaways from our conversation. And…listen to the recording of our full conversation on the Design Shift podcast and the Design Shift YouTube channel.

Before I go on, I’d love your help in spreading the word about Design Shift. To make this an even more valuable value proposition, I’m giving away five copies of Kevin and Jeanine Flores’s book, Design Career Handbook, at random. Refer just TWO (2) friends or colleagues to Design Shift. And when then subscribe, you’ll be automatically entered in the drawing.

I’ll pick the 5 lucky winners at random on May 24th, 2025, and will publish their names in the Design Shift newsletter the following week.

Here are the main takeaways from my conversation with Kevin Flores…

🧭 Lesson 1: Design’s real value? It shows up in the outcomes.

“Designers are often taught to talk about outputs—what we made, how we made it. But if you want to lead, you have to talk about outcomes. What changed? Who benefited? What moved the business forward?”

Kevin’s point: craft alone isn’t enough. If you want a seat at the strategy table, you have to show that your work delivers both value and velocity. How do (or will) your designs and/or leadership and mentorship of other designers create real value for the customer and for the company? How might you show that you’re always moving forward, not only delivering more value, but also learning from the successes and mistakes?

🌱 Lesson 2: Your career path won’t be linear—and that’s your edge.

From agency founder to government innovator to VP of Product, Kevin’s résumé doesn’t follow a straight line—and that’s the point. “Every pivot expanded my view. I learned to lead through influence, not just expertise.”

For designers, product managers, and everyone in between, wondering if it’s okay to take an unexpected turn? It’s not just okay—it’s powerful. It’s by plotting a distinct throughline in your resume, CV, bio, etc., that you can tell a story about how you’ve helped every organization you’ve worked with grow. In fact, we’ve heard (and witnessed) this time and time again. Interesting people hire interesting people. And…interesting people have interesting, nonlinear career paths.

🔣 Lesson 3: Generalist or specialist? Be both.

The old career debate—T-shaped or I-shaped—misses the point. “Designers who go deep in craft and broad across disciplines are the ones who thrive in modern orgs,” Kevin explained. It’s not about choosing; it’s about layering.

Anyone can say they’re T-shaped. But it’s the designers and product managers who can show they’re adaptable that will win the game. Plus…more experience + hobbies = an interesting person to work with.

Want to show that you’re a great person to work with? As a bonus, find a way to talk about or show what you do outside of work. At the end of the day, we’re working with people who live real lives and do some cool sh!t when we’re not at the office.

Lesson 4: Storytelling isn’t a soft skill—it’s a survival skill.

“Influence doesn’t come from having the best deck,” Kevin says. “It comes from telling the best story.” He shared how cross-functional teams remember and act on stories, not specs. If your team can’t explain your thinking to someone else, the design stalls out.

Learn what makes the person on the other side of your story tick. What do they need to hear? What metrics matter to them? How might they become the hero of your story?

Make your work memorable, not just logical.

📊 Lesson 5: Learn to speak ‘product’—especially in numbers.

Kevin emphasized that data literacy is one of the fastest ways to build trust. “Designers don’t need to be analysts, but we do need to understand the signals and metrics that matter.”

We all know that design isn’t just about making pretty things (or making things pretty). It’s about creating value. And…value always comes in two forms: qualitative and quantitative. These go hand in hand.

A great customer quote (qual) paired with metrics (quant) that show there are multitudes of customers who feel the same way is a surefire way to get you a seat at the “strategic table”.

If you can show how a design decision affects churn, conversion, or lifetime value, you’ll earn credibility fast—especially with product and engineering peers.

🔁 Lesson 6: Ditch the swim lanes—then step up and own the call.

One of the strongest patterns in Kevin’s leadership experience is the power of co-creation—followed by decisive ownership. “Shared input is great,” he said. “But once we align, someone needs to drive. Design leaders need to get comfortable making the call.”

This doesn’t mean dominating the room—it means moving the team forward when others hesitate. Use your design superpowers to guide teams, making decisions that are grounded in value creation.

🌍 Lesson 7: Want meaning and momentum? Go design what’s broken.

If you ask Kevin where design is needed most—it’s in public systems. “Government. Education. Health. These systems are messy, but they’re where design can be transformational.”

These spaces might not always pay top-tier salaries up front—but the opportunity to drive change is enormous, and often more visible than in big tech.

🧠 Final Wisdom: Your network is your long game.

Every major career move Kevin made came from a relationship. Not a cold job board. Not a perfectly polished résumé. “People remember how you show up,” he said. “Sometimes years later, when they’re deciding who to trust with the next big opportunity.”

Even when Kevin self-admittedly burned a bridge to the ground, he had created so much value and goodwill that years later, the very people in his network who were on the other side of that bridge came calling for help.

It can’t be said enough: trust, generosity, and long-term relationships often move your career further than any job application.

Listen to the recording of our full conversation on the Design Shift podcast and the Design Shift YouTube channel.