In this episode of Design Shift, I talk with Gregory Stock—fractional Chief of Staff, design strategist, and executive coach—about what it takes to lead with empathy, taste, and strategic clarity in an age defined by speed and AI.

Gregory shares his journey from the art world to the world of startups, revealing how his early work in museums shaped his approach to systems thinking, storytelling, and design at scale. We dive into his experience with The Bay Lights project in San Francisco, the power of deep listening in client work, and why he believes taste is something you build through time, discomfort, and curiosity.

He also opens up about how the DMBA program helped him close a “big empathy gap,” how he uses AI as a tool for dialogue—not just output—and what advice he has for the next generation of design leaders navigating ambiguity and change.

If you’ve ever wrestled with what it means to be both creative and strategic—or wondered how to stay grounded while working at the edges of art, business, and technology—this episode is for you.

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