The Question: Design System Collaborative Learning

Episode 076 Recap: Enabling Craft Through a Design System with Ben Callahan and ToniAnn Drenckhahn Ben Callahan and ToniAnn Drenckhahn recorded this recap the morning after their community deep dive, reflecting on what stood out from the data and the conversation. The survey went out to 1,105 design system practitioners; 64 responded. Topics include the distinction between craft and quality, two f...

Episode 076 Deep Dive: Enabling Craft Through a Design System with Ben Callahan and ToniAnn Drenckhahn Ben Callahan is joined by ToniAnn Drenckhahn, a design systems leader currently at Etsy and formerly at BetMGM, where her work on primitive components and foundational design quality prompted this episode's question. The survey drew 64 responses from 1,105 practitioners and surfaced a striking fi...

Episode 075 Recap: The Design System Identity Crisis with Ben Callahan and Cassie Groos In this recap of Episode 075, Ben Callahan and Cassie Groos unpack what they learned from the community on the subject of the design system identity crisis. Cassie is preparing a talk on this theme for Hatch Conference in Berlin and used The Question as her research engine. The survey was sent to 1,083 design s...

Episode 075 Deep Dive: The Design System Identity Crisis with Ben Callahan and Cassie Groos In this deep dive, Ben Callahan is joined by Cassie Groos — a freelance design systems specialist whose work spans consultancy, multi-brand systems, and the Hermes-to-Every rebrand — to explore what she calls the design system identity crisis. Cassie comes prepared: she's building out this topic as the focu...

In this recap of Episode 074, Ben Callahan is joined by Kaelig Deloumeau-Pregent to share what we learned on the subject of AI and design system visibility. The conversation traces a question Kaelig first answered nearly a decade ago at a Salesforce symposium: How do we actually know how our design system is being used? We wondered how that question lands today as AI accelerates content, design, a...

Episode 074 Deep Dive: AI and Design System Visibility with Ben Callahan and Kaelig Deloumeau-Pregent In this deep dive, Ben Callahan is joined by Kaelig Deloumeau-Pregent—a veteran design system practitioner whose career has spanned the BBC, The Guardian, Financial Times, Salesforce, Shopify, Netlify, and most recently Intuit—to explore the intersection of AI and design system visibility. Kaelig...

Episode 073 Recap: Design System AI Automation with Ben Callahan and Davy Fung Host Ben Callahan and co-host Davy Fung, a product designer on the Atlassian Design System and host of the Design System Office Hours podcast, sit down immediately following the Episode 073 deep dive to reflect on what they heard from the community. The survey was sent to 1,077 design system practitioners and received 1...

Episode 073 Deep Dive: Design System AI Automation with Ben Callahan and Davy Fung Host Ben Callahan is joined by co-host Davy Fung, a product designer on the Atlassian Design System (previously Meta) and host of the Design System Office Hours podcast, to explore AI as automation in design systems—what could be automated, what should be automated, where practitioners draw the line, and what "craft...

Episode 072 Recap: Extreme Design System Support with Ben Callahan and Doug Neiner Host Ben Callahan and co-host Doug Neiner, a design system practitioner at Planview, sit down immediately following the Episode 072 deep dive to reflect on what they heard from the community. The survey was sent to 1,081 design system practitioners and received 49 responses across four questions: what support do you...

Episode 072 Deep Dive: Extreme Design System Support with Ben Callahan and Doug Neiner Host Ben Callahan is joined by co-host Doug Niner, a design system practitioner at Planview, to explore extreme design system support—what it looks like, what gets in the way, and what truly moves the needle with consuming teams. The survey was sent to 1,081 design system practitioners and received 49 responses...

Episode 071 Deep Dive: The Criticality of Design Systems with Ben Callahan & Vitaly Friedman In Episode 071, host Ben Callahan is joined by co-host Vitaly Friedman—UX Lead, author, and founder of Smashing Conference—for a deep dive into the criticality of design systems. Vitaly brings experience from complex enterprise environments, including a multi-year engagement consolidating 199 European...

Episode 071 Recap: The Criticality of Design Systems with Ben Callahan & Vitaly Friedman Introduction Host Ben Callahan and co-host Vitaly Friedman reflect on the insights from the Episode 071 deep dive on the criticality of design systems. Vitaly is a UX lead, founder of Smashing Conference, and practitioner working in complex enterprise environments—most recently with the European Parliament...

Introduction Host Ben Callahan is joined by co-host Hannah Clarke, UI Engineer at Intapp, for a live deep dive on building design system infrastructure that lasts. The survey went to 1,061 practitioners and received 45 responses across four questions: company leadership model, dedicated team roles, who owns coded component delivery, and what actions create a system that endures. The conversation s...

Episode 070 Recap: Lasting Design System Infrastructure with Ben Callahan & Hannah Clarke This episode is made possible by Mintlify. If your design system documentation lives in five places and satisfies no one, Mintlify can provide one beautiful, AI-powered home for everything your team builds (and the why behind those decisions). Try it free → https://bit.ly/try-mintlify (use code MINT-THEQ...

Episode 069 Recap: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimaa Hassan --- Introduction In Episode 069 of The Question, host Ben Callahan (founder of Sparkbox and Redwoods Design System Community) sits down with co-host Shimaa Hassan. The conversation centers on one of the most persistent challenges in design systems work: how do you rebuild the foundation while the plane i...

Episode 069 Deep Dive: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimaa Hassan Introduction In episode 069 of *The Question*, host Ben Callahan (founder of Sparkbox and the Redwoods Design System Community) sits down with co-host Shimaa Hassan to tackle one of the most universal challenges in the space: rebuilding a design system while the products it supports are still in prod...

Episode 068 Part II Deep Dive: Design Systems as AI Context with TJ Pitre Aired live: February 20, 2026 Introduction In Part II of Episode 068, host Ben Callahan is joined again by co-host TJ Pitre—founder of Southleft, a front-end design development agency specializing in the intersection of AI and design systems—for a live community deep dive. This episode builds on Episode 068 Part I's explorat...

Episode 068 Recap: Design Systems as AI Context with Ben Callahan & TJ Pitre Introduction Welcome to The Question Episode 068 Recap. In this episode, Ben Callahan and co-host TJ Pitre facilitate a deep dive into one of the most pressing topics in the design system space today: Are our design systems ready to serve as reliable AI context? Ben sent a three-question survey to 1,031 design system...

Episode 068 Recap: Design Systems as AI Context with Ben Callahan & TJ Pitre Introduction Welcome to The Question Episode 068 Recap. In this episode, Ben Callahan sits down with TJ Pitre—founder of South Left studio—to unpack the results from this week's survey on design systems as AI context. Ben sent the three-question survey to 1,031 design system practitioners and received a record 148 res...

Episode 067 Deep Dive: Design Systems That Differentiate Introduction Welcome to The Question Episode 067 Deep Dive. Host Ben Callahan is joined by Yesenia Perez-Cruz—author of Expressive Design Systems and former design systems leader at Vox Media and Shopify—for an interactive conversation about design systems that differentiate. This session brings together dozens of design systems practitioner...

Episode 067 Recap: Design Systems That Differentiate with Ben Callahan and Yesenia Perez-Cruz Introduction Welcome to The Question Episode 067 Recap. In this episode, Ben Callahan sits down with Yesenia Perez-Cruz—author of Expressive Design Systems and design system consultant, to unpack the results from this week's survey on design systems that differentiate. Ben sent the three-question survey t...

The Question Episode 066: The Design System Learning Curve with Ben Callahan & Laura Kalbag Ben and Laura lead the community through a conversation about how people learn design systems, revealing that 75% feel qualified despite most being self-taught. The discussion explores whether the field needs W3C-style industry standards, with answers nearly evenly split between yes, no, and other. Comm...

Episode 66 Recap: The Design System Learning Curve with Ben Callahan and Laura Kalbag Ben and Laura unpack the episode 066 deep dive conversation on how people learn design systems, exploring why imposter syndrome is so prevalent in this space, the challenges of being self-taught in a field with no formal education path, and how the community might create better learning resources and pathways for...