
The Question is a collaborative learning podcast about Design Systems. Smart people like you sign up, answer a few niche questions about design systems for each episode, and then we all get together to unpack the data we've gathered. Each week, I'll invite a new co-host to help facilitate the conversation. After the deep dive, the co-host and I record a recap of what we learned. That means, for ea... more
| Publishes | Daily | Episodes | 31 | Founded | 8 months ago |
|---|---|---|---|---|---|
| Number of Listeners | Category | Technology | |||

To celebrate 80 episodes, Ben Callahan is joined by Robin Di Capua and Taylor Cashdan, who built the Redwoods Compass, a self-reflective tool for looking at design system health without grading it.
The survey went to 1,118 design system practitioner... more
Ben Callahan is joined by Robin Di Capua and Taylor Cashdan, members of the Redwoods Design System Community who spent nearly a year building the Redwoods Compass. Robin has worked as a designer since 2009, has focused on systems since 2016, and rece... more
Episode 079 Recap: The Evolution of Design System Documentation with Ben Callahan and Afyia Smith
Ben Callahan and Afyia Smith, a content designer and technical writer specializing in design systems, recap what the community said about who owns docu... more
Episode 079 Deep Dive: The Evolution of Design System Documentation with Ben Callahan and Afyia Smith
Ben Callahan is joined by Afyia Smith, a content designer and technical writer who spent five years as a documentation specialist on the design sys... more
Ben Callahan and Kacey Wood, Product Designer for Design Systems at Tabs, explore the psychology behind design system buy-in, the question Kacey brought after wondering what a design systems college curriculum would actually need to cover beyond toke... more
On Episode 078, Ben Callahan is joined by Kacey Wood, Product Designer for Design Systems at Tabs and member of Redwoods design system community. She and Ben open the floor to the community on the psychological side of systems work.
The survey went ... more
Ben Callahan welcomes Lauren LoPrete, Head of Design Foundations at Mercury, back to the show to talk through design system culture versus compliance—the tension between earning adoption and enforcing it. Fresh off Lauren's Config talk on design syst... more
Ben Callahan hosts the Episode 077, full community deep dive with Lauren LoPrete, Head of Design Foundations at Mercury, who has built and led design systems at Expedia, Dropbox, and Block. Lauren opens with her own arc, years spent grasping for cont... more
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This show centers on design systems as a collaborative learning journey. Each episode features practical deep-dives and recap conversations that unpack how design systems govern teams, governance, and craft at scale. Across episodes, listeners hear discussions about documentation, adoption psychology, governance models, AI integration, and enabling workflows, all grounded in real-world experiences from large and small organizations. The format emphasizes data-driven insights, actionable frameworks, and community participation, making it a valuable resource for practitioners who want to improve system ownership, cross-team collaboration, and the craft of building scalable design ecosystems. A notable strength is the recurring focus on govern... more
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Recent guests on this podcast include:
1. Robin Di Capua
2. Taylor Cashdan
3. Afyia Smith
4. Kacey Wood
5. ToniAnn Drenckhahn
6. Cassie Groos
7. Kaelig Deloumeau-Pregent
8. Davy Fung
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