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Artwork for The Question: Design System Collaborative Learning

The Question: Design System Collaborative Learning

Ben Callahan
Design Systems
Artificial Intelligence
Figma
Design System Documentation
Design System
Craft
Culture
Product Differentiation
Planview
Quality
AI (artificial Intelligence)
Design System Health
Leadership
Visual Communication
Operational Efficiency
Artificial Intelligence In Documentation
Open Source Technology
User Interface Design
AI Integration
Collaboration

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

PublishesDailyEpisodes31Founded8 months ago
Number of ListenersCategory
Technology

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Artwork for The Question: Design System Collaborative Learning

Latest Episodes

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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Recent Guests

Robin Di Capua
Co-presenter discussing design system maturity and the Compass
Redwoods Design System Community
Episode: Episode 080 Deep Dive: Visualizing Design System Health with Ben Callahan, Robin Di Capua, and Taylor Cashdan
Taylor Cashdan
Co-presenter discussing design system health and visualization
Redwoods Design System Community
Episode: Episode 080 Deep Dive: Visualizing Design System Health with Ben Callahan, Robin Di Capua, and Taylor Cashdan
Afyia Smith
Design systems practitioner and advocate with deep experience in design system documentation
Episode: Episode 079 Recap: The Evolution of Design System Documentation with Ben Callahan and Afyia Smith
Kacey Wood
Co-host bringing psychology of design systems to the discussion
Design Systems practitioner
Episode: Episode 078 Deep Dive: The Psychology of Design Systems with Ben Callahan and Kacey Wood
ToniAnn Drenckhahn
Guest facilitator discussing enabling craft through design systems
Etsy / Redwoods Design System Community
Episode: Episode 076 Deep Dive: Enabling Craft Through a Design System with Ben Callahan and ToniAnn Drenckhahn
Cassie Groos
Design system practitioner and speaker
Episode: Episode 075 Recap: The Design System Identity Crisis with Ben Callahan and Cassie Groos
Kaelig Deloumeau-Pregent
Design systems expert known for work with Design Tokens Community Group
Episode: Episode 074 Deep Dive: AI and Design System Visibility with Ben Callahan and Kaelig Deloumeau-Pregent
Davy Fung
Design systems practitioner, Atlassian
Atlassian
Episode: Episode 073 Recap: Design System AI Automation with Ben Callahan and Davy Fung
Doug Neiner
Guest on recap, discussed Extreme Design System Support and embedding
Episode: Episode 072 Recap: Extreme Design System Support with Ben Callahan and Doug Neiner

Host

Ben Callahan
Host of The Question: Design System Collaborative Learning

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Talking Points

Recent interactions between the hosts and their guests.

Episode 080 Recap: Visualizing Design System Health with Ben Callahan, Robin Di Capua, and Taylor Cashdan
Q: What has prevented your team from having an honest conversation about your design system's health?
The discussion highlighted that traditional metrics focus on components and documentation, while true health is about people, processes, governance, and culture, which can be intangible and vary by organization.
Episode 080 Recap: Visualizing Design System Health with Ben Callahan, Robin Di Capua, and Taylor Cashdan
Q: What methods or tools do you use today to measure or monitor the health of your design system?
Participants described a range of artifact-focused metrics but emphasized that health cannot be reduced to a single score; the tool should provoke discussion and self-reflection within teams.
Episode 079 Deep Dive: The Evolution of Design System Documentation with Ben Callahan and Afyia Smith
Q: Afyia, tell us a little bit about your background and how you got into design system documentation.
Afyia describes seven years in the design system space, starting as a UX/UI designer at EA, where she wrote docs while building the library, and later focusing entirely on documentation. She details experiences across design systems at Epic Games, working on Fortnite and Epic Design System, learning DOCSIS workflows, governance, and AI readiness frameworks.

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Frequently Asked Questions About This Podcast

What is This Podcast about and what kind of topics does it cover?

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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1. Design System Office Hours

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this podcast launched 8 months ago and published 31 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on this podcast?

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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