HeyJaredThe Question: Design System Collaborative Learning
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.
- Indexed episodes, last 90 days
- 8
- Latest publication
- Sep 23, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 13, 2026
Latest episodes
Episode 080 Recap: Visualizing Design System Health with Ben Callahan, Robin Di Capua, and Taylor Cashdan (opens the original)
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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 practitioners and received 52 responses to two questions, along with a first-ever homework assignment: a blank spider chart to fill in by instinct. The conversation covers what "health" even means, how the Compass's six categories emerged from Redwoods workshops,
Episode 080 Deep Dive: Visualizing Design System Health with Ben Callahan, Robin Di Capua, and Taylor Cashdan (opens the original)
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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 recently joined the design system team at GetYourGuide in Zurich. Taylor has spent six years as a systems practitioner across enterprise, startup, and consulting teams. The survey went to more than 1,100 practitioners and received 52 responses to two que
Episode 079 Recap: The Evolution of Design System Documentation with Ben Callahan and Afyia Smith (opens the original)
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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 documentation and where docs are headed now that machines are reading them too. The survey went to more than 1,100 design system practitioners and drew 61 responses across five questions. The conversation covers the shift from prose to structured content,
Episode 079 Deep Dive: The Evolution of Design System Documentation with Ben Callahan and Afyia Smith (opens the original)
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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 system team at Epic Games, built AI readiness frameworks and governance models there, and now collaborates with PJ Onori on the DSDS documentation spec. Together with the community, they dig into who owns design system documentation and what changes when
Episode 078 Recap: The Psychology of Design Systems with Ben Callahan and Kacey Wood (opens the original)
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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 tokens and components. The survey went out to over 1,100 design system practitioners and drew 50 responses across four questions. The conversation covers reactance theory, the endowment effect, curse of knowledge, social proof, the IKEA effect, foot-in-t
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