Building Trust Before Direct Feedback

We’ve worked alongside people for years, only to realize that we know nothing about their personal life. And it probably affected our working relationship. Knowing your colleagues as humans reframes inevitable challenges at work. Had we known our colleagues better, would we have worked through disagreements better or found new ways to collaborate? Yeah, we sure would have.

Alison Rand, who helped establish the discipline of design operations through roles at Hot Studio, Frog, Automattic, and SAP, explores building relationships at work in her new book Sentido—a term that encompasses both making sense of things and feeling them deeply.

In our conversation, Alison challenges the Silicon Valley orthodoxy of radical candor with her concept of radical humanity. She also explains why designops is fundamentally heart-driven work, and draws unexpected parallels between organizational dynamics and the regenerative systems of Puerto Rico’s El Yunque rainforest.

Bio

Alison Rand brings a unique perspective forged in the crucible of real experience. A native NewYorker who lost her mother at sixteen, she learned early that life rarely follows neat narratives. Her career trajectory—from navigating the male-dominated agency world to building design operations practices at scale—taught her that the skills needed to thrive professionally often mirror those learned navigating the New York subway in the 1980s. After being laid off the same week MIT Press accepted her book proposal, she retreated to the woods to write what became part memoir, part radical reimagining of design leadership.

She makes the case that organic intelligence matters as much as academic credentials, and that the future of design leadership lies not in prescriptive frameworks but in building cultures of genuine mutualism.

Whether you’re wrestling with organizational transformation or questioning the artificial boundaries between personal and professional identity, Alison offers hard-won wisdom about leading with both courage and compassion in spaces that often reward neither.

***

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books:

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid