What shape(s) does design take when confronted with art, technology, and differing tastes?

Design is leadership. It’s how we frame problems, guide teams, and move ideas from concept to impact. To me…that’s a profound statement. Say it again with me: design is leadership. Feels good, doesn’t it?

In this issue, I sit down with Gregory Stock, a design strategist, executive coach, and fractional Chief of Staff (at two completely different design agencies!) to explore why great strategy starts with deep listening, how taste is cultivated over time, and what art can teach us about infrastructure, empathy, and AI. Gregory’s path from museum educator to civic-scale designer is filled with insight for anyone looking to lead with more clarity, humanity, and intention.

In this issue/episode:

1. Design Strategy Starts With Deep Listening

2. Taste Is Learned…And It Takes Time

3. From Museums to the Bay Lights to AI: Designing at Civic Scale

Read on for my main takeaways from our conversation. 🎧 And…listen to the recording of our full conversation on the Design Shift podcast on Spotify and Apple and the Design Shift YouTube channel.

— Justin Lokitz

Design Deep Dive

Design is listening (and vice versa).

Gregory didn’t take the typical path into design strategy. He started out in the art world, from museum education, nonprofit leadership, and historical curation. He was on track to become a museum director…in fact, that was his original dream. But along the way, something shifted. He wanted to shape the future.

Today, Gregory operates at the intersection of design, foresight, and leadership. He’s a fractional Chief of Staff for two different agencies, Secret Sauce and SWARM, an executive coach, and a strategist who’s worked across proptech, cleantech, edtech, public health, and the arts. He’s also a DMBA graduate who credits design with transforming how he thinks, listens, and leads.

We spoke about the through-lines in his career, what it means to design a life, how taste is cultivated over time, and why art and strategy are absolutely, unequivocally inseparable.

Here are the three biggest takeaways from our conversation…

1. Design Strategy Starts With Deep Listening

For Gregory, design strategy is as much about co-creation as it is about stepping back and listening…deeply, deliberately, and without ego. Strategy, in his view, isn’t a static framework or a clever plan to be delivered. It’s something you build with people, not for them. And it begins by understanding not just what’s being said, but what’s being felt.

When Gregory entered the DMBA program, he believed he was already a strong communicator. But the program revealed something deeper. He wasn’t yet listening to understand—he was listening to respond (as many of us do). The shift came when he realized that the real value of design strategy is in your ability to center someone else’s needs, language, and worldview, irrespective of the outcome.

Today, Gregory leads with that same orientation, whether he’s guiding a Series A brand through a repositioning or helping a legacy institution design a new digital product. His first move isn’t ideation. It’s attunement.

This mindset allows him to identify the real problem under the stated one, the friction behind the brief. It’s not always obvious. It rarely shows up in a scope of work. But it’s almost always there, just beneath the surface, waiting to be named.

Gregory sees himself as a mirror. He listens, reflects, reframes. He plays back what he hears in new language until it finally lands. In doing so, he helps clients hear themselves clearly for the first time. That, he believes, is when strategy begins—not with answers, but with clarity.

2. Taste Is Learned…And It Takes Time

In a world where designers are urged to move fast, ship often, and optimize everything, Gregory offers a quieter, more deliberate perspective: taste is slow. Taste is built. And without it, nothing you make—no matter how efficient or technically perfect—will resonate.

For Gregory, the journey began in the backseat of a car. His older brother, a Gen Xer (like yours truly) with strong opinions and sharper playlists (like yours truly), would quiz him on band names as the radio played. Gregory never knew the answer…and it drove him crazy. But instead of giving up, he got curious. He started learning the names. Then the genres. Then the histories behind them.

That instinct—to dig deeper, to get uncomfortable, to figure out why something works—became a foundation. Today, he applies the same process to everything from architecture and literature to client feedback and generative AI.

Gregory doesn’t see taste as a gift you’re born with. It’s a habit. A willingness to notice what moves you and to ask why. It’s also an act of editing, choosing what to embrace, what to question, and what to discard.

Over time, those choices shape a point of view. And in the age of AI, that point of view matters more than ever.

AI, Gregory believes, doesn’t replace designers with taste; it reveals who has it. Tools like ChatGPT, Midjourney, and Claude aren’t shortcuts. They’re mirrors. They reflect your inputs, your style, your patterns of thought. The better you know your own lens, the more powerful those tools become.

Taste, in the end, isn’t a filter…and a foundation.

3. From Museums to the Bay Lights to AI: Designing at Civic Scale

Like many of us, Gregory’s career path doesn’t follow a linear arc; it spans disciplines, sectors, and scales. He began in the world of art and museums, curating experiences meant to provoke reflection and expand public understanding. His shift into tech ended up amplifying this.

That forward-looking curiosity defined one of Gregory’s most iconic projects: The Bay Lights. Working with Illuminate, the nonprofit behind the 1.8-mile LED sculpture on the western span of the San Francisco Bay Bridge, Gregory helped transform a bold artistic concept into a functioning, large-scale public experience.

But The Bay Lights did more than beautify infrastructure. It reshaped how people saw—and cared for—that infrastructure. It changed the way Caltrans, the California Department of Transportation, maintained the bridge.

That’s the question Gregory keeps asking as he navigates the next frontier: artificial intelligence. He doesn’t just use AI tools—he interrogates how they shape design choices, influence trust, and mirror human inputs. For him, tools like ChatGPT and Midjourney are as much tools for productivity as they are new civic materials.

Gregory sees design at civic scale as less about monumentality and more about responsibility. Whether it’s a light installation, a software product, or an AI interaction, the goal is the same: build with intention. Lead with story. Design for systems, not just screens.

That hasn’t changed. What’s changing is the scale of what we’re asked to imagine—and the tools we now have to do it.

Justin’s Notes

At the end of our conversation, Gregory brought it full circle: “Your job is to know yourself better than your client. And not judge them—just understand yourself.”

It’s a simple idea, but a powerful one…especially in a time when strategy is too often mistaken for frameworks, and taste is reduced to trend cycles. Gregory reminds us that design and design strategy, at their core, are deeply human work. These are about making sense of needs, of tensions, of possibilities.

And in a world shaped more and more by generative tools and accelerated timelines, the designers who will lead are cultivating inputs as much as they’re generating outputs. They’re the ones who listen better, who think in systems, who refine their perspective over time, and use that perspective to shape work that matters.

Design isn’t neutral. It never has been. Whether we’re lighting up a bridge, shaping a product, or prompting an AI model, we’re building narratives, setting defaults, and influencing the way people live and work. Taste, empathy, and strategic clarity are essential tools for designing responsibly at scale.

That’s why conversations like this matter…and why we’ll keep having them. If we want to lead with design, we need to listen with intention, think with depth, and act with courage. Just like Gregory does.

Want more? Connect with Gregory and tell him Justin sent you!

Resources

• Secret Sauce

• SWARM

• Design MBA @ CCA

Subscribe to Design Shift for more conversations that help creative professionals grow into strategic leaders.