Podcast
The Question: Design System Collaborative Learning
Hosted by Ben Callahan
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 each episode, you can listen to the recap and the full deep dive! If you're a design system practitioner, subscribe today (https://bencallahan.com/the-question) to receive an invitation to each episode. This only works if the community joins in! Stay in learning mode ❤️
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Episodes
- Episode 074 Recap: AI and Design System Visibility with Ben Callahan and Kaelig Deloumeau-PregentMay 13, 2026 · 38 minIn 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, and code production. The survey was sent to over 1,000 design system practitioners and received 78 responses across four questions: (1) current level of visibility into how design system assets are used across disciplines, including by AI; (2) biggest design system concerns as agents and automation produce more content at scale; (3) how the right balance between enforcement and enablement has shifted as AI enters the picture; and (4) the one thing they'd implement today to improve visibility without becoming the design police. Ben and Kaelig dig into a striking correlation between visibility maturity and enforcement-versus-enablement preferences, the "fog of war" metaphor for systems work, why accessibility may not belong inside design systems, and what shifting roles mean for designers in an agent-driven future. Show Notes 00:00 — Welcome and reintroducing Kaelig 00:28 — The 2016 Salesforce symposium and a decade-old magic wand question 03:03 — A business opportunity: cross-discipline visibility tooling 03:39 — Walking through the four survey questions and methodology (1,000+ sent, 78 responses) 05:53 — Kaelig's in-progress article and crowdsourcing community thinking 08:26 — Question 1: Self-reported visibility levels and what surprised us 09:14 — Why design systems are for people, and the limits of robotized outreach 10:38 — Visibility as stacked layers, not a single maturity rung 11:00 — Question 2: When every concern is a top concern 12:24 — Why feedback loops may be the most critical concern 13:04 — Question 3: The balanced split on enforcement vs. enablement 14:35 — Pace layers, time, and when to enforce vs. let people roam 16:35 — Does accessibility actually belong inside the design system? 18:53 — Design system teams becoming the org's AI product-builder definers 19:30 — Educating the designers of tomorrow (including agents) 20:30 — The legal-approval bottleneck slowing AI enablement 20:55 — A standout open response: lightweight embedded signal collection at the point of consumption 21:46 — Just-in-time guidance and bringing developer experience to designers 22:31 — Pegah Amadi's Magnolia and weaving signals into workflow 23:00 — The "Fog of War" metaphor: attention as a system team's scarcest resource 24:48 — Sending scouts: proactive visibility across Slack, Drive, and roadmaps 27:03 — De-risking and saying no when the landscape shifts 28:30 — Cheap scouting with sentiment analysis and lightweight tooling 29:26 — Mapping Question 1 against Qu
- Episode 074 Deep Dive: AI and Design System Visibility with Ben Callahan and Kaelig Deloumeau-PregentMay 13, 2026 · 52 minEpisode 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 shares how a question raised back in a 2016 design systems symposium ("If you had a magic wand, what would you change?") still resonates today: practitioners want more visibility into how their systems are actually being used. The survey was sent to 1,081 design system practitioners and received 78 responses across four questions: current level of visibility into design system asset usage, biggest concerns as AI agents produce content at scale, how the enforcement vs. enablement balance has shifted with AI, and what one thing they'd implement to improve visibility without becoming the "design police." The conversation explores the "fog of war" metaphor for incomplete knowledge in systems work, the tension between surveillance and creative freedom, librarians vs. police as governance models, and how AI changes who (or what) is deviating from the system. Show Notes 00:39 — Kaelig's background: from a French web agency to BBC, Guardian, FT, Salesforce, Shopify, Netlify, and Intuit 06:56 — Becoming a systems thinker before "design systems" was a career 07:38 — The 2016 magic-wand question and why visibility is still the wish 08:34 — Walking through the four survey questions 09:22 — Survey methodology: 1,081 practitioners, 78 responses 10:04 — Reviewing Q1: most teams have manual or partial visibility, very few have robust automated tracking 12:01 — Visibility isn't just internal; the end customer dimension and zombie code 12:27 — Q2 results: AI concerns are "all of the above," and Brandon's optimistic reframe 13:26 — Q3 results: enforcement vs. enablement is balanced, with 14% choosing "other" 14:35 — The "fog of war" metaphor and the risk of a design system surveillance state 17:02 — Peter on cultural contracting and counterbalancing forces in an org 18:58 — The "helpful Clippy" view: visibility as a signal for better docs and training 21:24 — Doug's question: is resistance to tracking a designer-specific concern? 22:13 — Greg on discipline, rigidity, and adapting design practices for AI workflows 24:22 — Lightweight, embedded signal collection at the point of consumption 25:31 — Magnolia and ESLint-style "disable with a reason" patterns for design 27:10 — Jeff on measuring adoption and building relationships to capture wins for leadership 29:48 — Alexander on percentile-matching to surface emerging patterns and snowflakes 32:02 — Pedro on treating deviations as a "confession room," not policing 33:53 — The correlation between visibility (Q1)
- Episode 073 Recap: Design System AI Automation with Ben Callahan and Davy FungApr 27, 2026 · 26 minEpisode 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 101 responses across four questions: what percentage of your workflow could be automated with AI today; what percentage should be automated; in what areas should we avoid AI automation and why; and what does craft mean to you in a 2026 design systems context. The conversation covers the gap between "could" and "should," the fear of loss embedded in resistance to automation, how process maturity should gate automation decisions, Bill's insight that automating broken processes masks their flaws, and the community's rich catalog of ways AI is already being put to practical, targeted use in design system workflows. Show Notes 00:00 - Introduction and episode overview 00:14 - Topic recap: AI as automation in design systems, four questions asked 01:51 - Davy's starting point: Zero Height report showing 63% not using design system automation 02:48 - Top-down AI mandates vs. practical decisions about what to automate 03:18 - What's missing from the conversation: automation's impact on human connection rituals 03:40 - The "could vs. should" gap: respondents who decreased their answer between Q1 and Q2 04:00 - What the decreasers said: loss of organizational context, institutional memory, and learning 05:01 - Davy's pushback: documented knowledge scales better than single points of contact 05:58 - The language of "loss" as sensitivity to losing control, not losing value 06:16 - Ben's process maturity model: automate after you've learned the lessons manually 07:11 - The risk of skipping straight to AI before understanding the work 07:45 - Davy: scalability vs. the trap of being the sole expert in your org 08:10 - Bill's insight from the deep dive: automating a process exposes its flaws — AI won't 17:24 - Ben recaps Bill's argument: AI is powerful enough to automate things you shouldn't 18:40 - Davy on CI pipeline linting: signals over blockers, data over gatekeeping 19:55 - Ben: injecting human review earlier in the process keeps the PR doing its job 20:35 - FigJam roundup: how community members are already using AI for automation 21:00 - Use cases shared: single-use plugins, token automation, GitHub workflows, dashboards, prototyping 21:37 - Davy: Atlassian's push toward higher-fidelity prototyping with AI tools 22:35 - Davy's underrated use case: Slack MCP to capture keywords and surface support patterns 23:11 - Ben: thin slices of AI help throughout the process vs. wide-scope automation 24:15 - Closing reflections on craft: Samantha's quote — "AI is the
- Episode 073 Deep Dive: Design System AI Automation with Ben Callahan and Davy FungApr 27, 2026 · 50 minEpisode 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" still means in 2026. The survey was sent to 1,077 design system practitioners and received 101 responses across four questions: what percentage of your workflow could be automated with AI today; what percentage should be automated; in what areas should we avoid AI automation and why; and what does craft mean to you in a 2026 design systems context. The conversation covers the surprising gap between "could" and "should," the risk of using AI to automate broken processes without questioning them first, the tension between deterministic tasks and those requiring human judgment, and how community remains the best antidote to feeling overwhelmed by an ever-accelerating tooling landscape. Show Notes 00:00 - Introduction and welcome 00:29 - Guest background: Davy Fung on design systems at Atlassian and Meta 01:27 - Design System Office Hours podcast approaching episode 100 01:56 - Topic framing: AI as automation in design systems 02:22 - Survey overview: the four questions asked 03:14 - Survey stats: 1,077 sent, 101 responses 03:44 - Framing quote from Greg: craft-driven practitioners as guardrail-keepers 04:37 - Q1 & Q2 findings: could vs. should be automated 04:59 - Davy's reaction: Zero Height report showed 60% not using token automation 05:28 - Ben's take: design systems are ripe for automation by definition 09:46 - Low-level manual work as craft: some practitioners prefer curation over automation 10:17 - Community opens up: automation as habit vs. automation as know-how 13:00 - The "could vs. should" gap: more caution than capability suggests 17:00 - Davy's workflow: starting ~60–70% of work with AI or automation support 23:34 - Bill's 0%/0% answer: automation exposes flawed processes AI won't question 25:27 - Key insight: automating a hard process can mask that the process itself is wrong 26:33 - Stephen's framework: black-and-white tasks vs. tasks needing intelligent reasoning 28:01 - Practical example: using AI to write consumer-friendly token changelog messages 29:57 - Connection to Episode 072: extreme support and openness to direct conversation 30:12 - Lauren: AI used to train teams on new tools, preserving human knowledge transfer 33:00 - Q3: areas to avoid AI automation — relationships, decision-making, creative direction 36:15 - The "CEO said something" problem: top-down AI mandates without practical grounding 36:43 - Skills vs. MCP: a lively side thread from the community 38:00 - Craft in 2026: intentionality, sys
- Episode 072 Recap: Extreme Design System Support with Ben Callahan and Doug NeinerApr 13, 2026 · 32 minEpisode 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 currently offer; how would you change it without constraints; what prevents better support; and share a story of going above and beyond. The conversation covers the standout data points: the written vs. video documentation gap, the surprisingly high rate of dev environment access, embedding, private vs. public support channels, the balance between high-touch support and burnout, and the importance of being perceived as a helper rather than a blocker. Show Notes 00:00 - Introduction and episode overview 01:46 - Q1 data highlights: written vs. video documentation gap 02:13 - Dev environment access: higher than expected at nearly 50% 02:48 - Lowering the bar for video production with modern tooling 03:15 - The perfectionist/design system practitioner Venn diagram 04:00 - Q3 data: unclear ownership is low; headcount and competing priorities dominate 04:30 - What "competing priorities" really means for system teams 05:46 - Doug's support approach at Planview: docs, Slack channels, onboarding, and local debugging 07:53 - Going beyond "access": running consumer products locally for deeper support 08:28 - The most extreme example: getting an org-issued PC to support a heavy product 09:42 - DMs vs. open channels: why private requests matter for trust 10:34 - Not everyone is comfortable asking publicly—meeting people where they are 11:20 - The problem with ticketing systems and over-streamlining support 11:49 - How private support builds trust that eventually leads to public participation 13:25 - Prioritizing relationship over efficiency: creating tickets on behalf of consumers 14:10 - Scale vs. effort framework for thinking about support types 15:42 - Embedding: initially looks high-effort/low-scale, but the impact compounds 16:21 - Doug on embedding: modeling behavior, referencing docs together, building self-sufficiency 17:50 - The other side: high-touch support and the risk of design system team burnout 18:47 - How to gauge when a support request warrants deep mentorship vs. a quick fix 21:56 - Recap of embedding discussion: Sean's reverse embedding process from Spotify 23:28 - Doug's one experience with reverse embedding and its lasting impact 24:06 - Alexander's story: misaligned incentives can undermine embedding programs 25:08 - Rebecca's insight: being a helper vs. a blocker, and how hard trust is to rebuild 26:06 - What embedding teaches you about your own system's pain points 26:31 - St
- Episode 072 Deep Dive: Extreme Design System Support with Ben Callahan and Doug NeinerApr 13, 2026 · 50 minEpisode 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 across four questions: what support do you currently offer; how would you change your program if unconstrained; what prevents better support; and share a story of going above and beyond. The conversation covers the surprising prevalence of dev environment access, the rarity and outsized impact of embedding, the tension between high-touch support and burnout, and why building trust may matter more than any specific tactic. Show Notes 00:00 - Introduction and welcome 00:37 - Guest background: Doug Niner on getting into design systems at Planview 01:38 - Topic framing: what is "extreme design system support"? 02:07 - Survey overview: the four questions asked 03:34 - Survey stats: 1,081 sent, 49 responses 03:59 - Q1 findings: what support are teams currently offering? 04:30 - Reactions: video vs. written docs, dev environment access 05:27 - Video documentation: perfectionism vs. "good enough" screen recordings 06:25 - Q3 findings: headcount, bandwidth, and competing priorities dominate 07:17 - Key insight: teams know what good looks like but lack people and time 09:10 - Embedding: high effort, but potentially exponential impact through advocacy 10:10 - Community discussion: what does "embedding" actually mean? 11:07 - Sean shares his team's embedding process: runbooks and buddy systems 15:36 - Alexander: forward embedding failures vs. reverse embedding wins 17:53 - Reverse embedding: consuming team members join the design system team 19:50 - Disruption and ROI: is onboarding a stream of embeds worth it? 21:16 - Turning embedded team members into lasting design system advocates 23:09 - Rapid bug turnaround as a trust-building extreme support tactic 24:57 - Embedded collaborators as a source of honest, continuous feedback 25:53 - "Runners": rotating on-call support roles and AI-assisted quick fixes 26:45 - Rebecca on trust: being a helper vs. a blocker 27:14 - Supporting private requests alongside public channels 28:35 - Over-systematizing support and why removing friction builds trust 29:31 - Q4 stories: going above and beyond for consuming teams 29:43 - Taylor's story: building buy-in for a generational system change at Fidelity 33:12 - Doug's story: burning trust with a team and winning them back over 18 months 34:37 - Mapping stakeholders from saboteur to advocate 35:30 - Jane's perspective: extreme support drives adoption but risks burnout 36:53 - Hand-holding vs. empowerment:
- Episode 071 Deep Dive: The Criticality of Design Systems with Ben Callahan & Vitaly FriedmanMar 29, 2026 · 52 minEpisode 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 Parliament websites into one across 25 languages. The survey was sent to over 1,000 design system practitioners, yielding 61 responses. Participants were asked four questions through the lens of their single most critical product: (1) what level of impact would a product failure have on end users—loss of comfort, discretionary money, essential money, or life; (2) the size of their engineering team; (3) how they ensure their design system supports that criticality; and (4) whether anyone in their org is doing workflow analysis with users. Show Notes 00:04 Introduction and episode overview 01:48 Vitaly's background: complex systems, B2B, insurance, European Parliament 03:01 The pressure of high-stakes work and measuring before/after impact 05:19 Ben's upcoming book, published by Smashing Magazine 05:44 Survey overview: methodology and FigJam data access 06:11 Q1 Results: 57% selected "loss of essential money"; write-in responses 07:08 Q2 Results: even distribution across team sizes; Cockburn's scale model 08:03 Vitaly on loss of trust and reputation as missing modern categories 09:29 Expanding the criticality framework for today's digital landscape 10:52 Defining workflow analysis vs. task analysis 14:33 Financial app example: importing a portfolio (task) vs. market analysis (workflow) 15:56 Key finding: workflow analysis correlates with team size, not criticality 17:23 Peter: using AI agents as a team of one to conduct workflow analysis 19:41 Community discussion: respondents who selected "loss of life" 20:09 David (Mayo Clinic): design system tokens and cascading patient-room risk 21:32 Taylor: higher criticality means more questions and stakeholders, not a different process 23:52 Vitaly: poor data visualization choices can cascade into financial loss 24:20 Reference: The Fifth Discipline by Peter Senge (1990) 25:08 Hattie (John Deere): autonomous vehicle safety warnings and multi-team sign-off 26:41 Jesse (NAVA): public benefits delivery—if this fails, someone doesn't eat 28:10 Vitaly: legacy systems as an underappreciated source of fragility and criticality 30:06 Taylor: legacy is an iceberg—you don't know what you've got until you knock 31:58 Kele: integrating a design system and AI tooling into existing enterprise SaaS 33:17 Level-setting AI expectations with leadership 35:42 Greg: AI tooling as a potential accelerator for legacy accessibility migration 39:38 Vitaly: migrating away from legacy means designing the change, not just t
- Episode 071 Recap: The Criticality of Design Systems with Ben Callahan & Vitaly FriedmanMar 29, 2026 · 38 minEpisode 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. The survey was sent to 1,069 design system practitioners and received 61 responses. Respondents were asked four questions through the lens of their single most critical product: how failure would impact end users (loss of comfort, discretionary money, essential money, or life); the size of the engineering team; how their design system supports that criticality and scale; and whether anyone in their org is doing workflow analysis with product users. Show Notes 00:00 - Welcome and introductions; Vitaly reflects on surprises from the deep dive 00:27 - How The Question works: survey Monday, deep dive Thursday, recap to follow 01:41 - The Coburn Scale and how it shaped the survey questions 03:45 - Survey results: why "loss of essential money" topped the criticality scale 04:23 - Vitaly's take: loss of reputation and trust as proxies for financial loss 05:30 - Write-in responses: loss of transparency, essential data, and future compatibility 07:28 - Hyper-personalization and ephemeral UI: validating experiences we can't fully see 08:50 - Decisions as infrastructure: encoding decisions into markdown and design systems 11:57 - Automation and AI across design, code, and UI—and what that means for human oversight 13:52 - "Flying blind": the risks of building layers atop systems we don't fully understand 16:30 - Defining workflow analysis vs. task analysis and why it matters 19:37 - The hypothesis: does higher criticality correlate with more workflow analysis? The data didn't confirm it. 22:01 - What the data did show: team size as a stronger predictor than criticality 25:32 - Design systems sandwiched between product teams and top-down quality guidelines 29:35 - Legacy software: an underappreciated risk factor and political minefield 32:39 - Migrating legacy means migrating flows, habits, and ways of working—not just UI 34:46 - What Vitaly is working on: events, video courses, design patterns, and upcoming books 36:14 - How to stay connected; Redwoods community open for membership --- Where to Find the Hosts Ben Callahan is Founder of Sparkbox and Redwoods Design System Community. Read his writings, have him present at your event, or engage with him as a coach or consultant at https://bencallahan.com Vitaly Friedman is a UX Lead and founder of Smashing Conference. Connect with him on LinkedIn https://bit.ly/43Iig8B Get the Raw Data Access the complete survey data from Episode 071 to conduct your own analysis: https://bit.ly/4rYcRTk Review the FigJam Note
- Episode 070 Deep Dive: Lasting Design System Infrastructure with Ben Callahan & Hannah ClarkeMar 16, 2026 · 53 minIntroduction 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 spans surprising results, web component delivery strategies, the framework agnostic debate, the unicorn-hire problem, API flexibility, and the human community that makes any system worth building. 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 for 50% off Pro for 6 months) Show Notes 00:02 — Welcome, Hannah's intro, and sponsor message (Mintlify) 01:07 — Hannah's background: UI Engineer at Intapp, full-stack roots, how she found the design systems space 03:25 — Survey overview: Four questions, 1,061 sent, 45 responses 04:39 — Q1: "Led by product" came in at ~40%, surprising Ben; Hannah less shocked given her experience 06:31 — Q2: Front-end dev outranked UI design in dedicated roles; reference to Sean Bent's post on design system hiring trends 08:22 — Community as infrastructure: Awareness and human connection matter as much as tooling; user showcase idea from Hannah's team retro 11:14 — Joshua: In-person labs where consuming teams experiment with the design system to make it feel engaging 12:13 — Hannah's delivery approach: Stencil + web components, outputting to multiple NPM packages (tokens, styles, web components, React 18, React 19 + SSR) 14:33 — Q4 theme: Framework agnosticism as a longevity strategy; design-side agnosticism and Penpot as a Figma alternative 16:50 — Josh: Journey from web components wrapped in React to going all-in on React and why 17:48 — Real challenges wrapping web components for React: Shadow DOM, team culture resistance, the "pure React" demand 19:09 — Post-processing scripts on top of Stencil: Default values, required props, types files, and developer quality-of-life improvements 22:50 — Guy: AI workflow from Figma to production code; using Figma Console MCP to convert prototypes into design-system-compliant files; circumventing design tools altogether 27:11 — Kelly: Laid off with her entire product design org; job postings pitting design vs. engineering; the value of tight cross-discipline colla
- Episode 070 Recap: Lasting Design System Infrastructure with Ben Callahan & Hannah ClarkeMar 16, 2026 · 32 minEpisode 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 for 50% off Pro for 6 months) Introduction In Episode 070 of The Question, host Ben Callahan sits down with co-host Hannah Clarke, UI Engineer at Intapp, to recap a conversation about building design system infrastructure that lasts. The episode drew from a survey sent to 1,061 design system practitioners, yielding 45 responses across four questions: which leadership model best describes your company (engineering, product, design, or balanced); which roles have at least one dedicated person on your design system team (DevOps, design ops, UI design, front-end dev); who owns responsibility for delivering coded components; and what actions create a system that endures. The conversation ranges from surprising survey results and the unicorn-hire debate to web component delivery strategies, framework agnosticism, and the human infrastructure that keeps systems alive. Show Notes 00:00 — Welcome & sponsor mention (Mintlify) 00:45 — Survey methodology recap: 1,061 sent, 45 responses, four questions reviewed 01:20 — Q1 results: Company leadership — "led by product" dominated; why that surprised Ben but not Hannah 02:35 — Low "led by design" responses: what does that say about design's seat at the table? 04:47 — Q2 results: Dedicated roles — front-end dev outranked UI design, which shocked both hosts 05:35 — Job posting trends: Why available design system roles skew toward design over engineering 06:49 — The unicorn problem: Companies asking for one person to do it all 07:20 — Greg's insight from the deep dive: "I want to use my code knowledge to do my design job better" 08:01 — Hannah's perspective: Understanding design makes you a better front-end developer, but specialisms matter 09:10 — Q4 highlight: "Connecting people that ask about the system — tools will keep changing, but people will keep interest alive" 10:02 — Human infrastructure: Why community-building is as foundational as technical tooling 11:36 — Data note: Over 60% of Q4 responses mentioned humans, people, community, champions, or trust 12:22 — The cultural hurdle: Solving a technical problem doesn't mean people will adopt it 13:13 — Framework agnostic vs. framework-specific: Three respondents advocated for agnosticism; Joanna's team built two separate libraries 14:08 — Hannah's approach at Intapp: Why they chose Stencil + web components and the longevity thinking behind it 15:43 — How they actually deliver components: NPM packages for tokens, styles, web components, React 18, an
- Episode 069 Recap: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimma HassanMar 2, 2026 · 22 minEpisode 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 is still flying? Ben and Shimaa share survey results from 1,061 design system practitioners (53 responses) and open the floor to a rich community discussion on versioning strategies, token architecture, breaking changes, and the ongoing tension between innovation and standardization. Survey questions asked: (1) How many times a month do you think about throwing your design system away and starting over? (Range: 0–5) | (2) If you chose to start over, what's the one decision you'd make differently on day one? | (3) How do you keep product teams confident in a system that's actively being rebuilt underneath them? | (4) Tell us a story about rebuilding a system mid-flight. --- Show Notes 0:05 — Introductions: Ben welcomes Shimaa Hassan as co-host for episode 69 0:18 — Episode context: rebuilding a design system mid-flight and how Ben and Shimaa connected 1:00 — Survey recap: the "how often do you think about starting over?" question and why Shimaa expected a higher number 1:36 — Data results: the ~50/50 split and overview of the three open-text survey questions 2:30 — The "fork and maintain" approach: letting teams use the old version while building the new one 3:19 — Shimaa's iterative approach: design rebuilt from scratch, engineering making incremental changes in code 4:53 — Step-by-step walkthrough: how Shimaa used the existing codebase and AI tools to inform the new architecture 7:29 — Systematizing what already exists: abstracting and naming tokens vs. inventing new ones 8:10 — Avoiding breaking changes: the strategy of supporting the live state while layering in improvements 9:29 — Finding the middle ground: honoring existing design before driving further evolution 10:30 — Multiple versions vs. iterative: Guy's semantic versioning approach vs. smaller teams who can't maintain parallel systems 13:30 — Taylor's poll: how few teams have actually had a formal, mandated migration period 15:00 — A model for splitting system team responsibilities: dedicated evolution vs. embedded implementation support 16:12 — Shimaa's experience at Square: rotation embeds and borrowing engineers between teams 17:15 — Empathy building through team exchange programs: pros, cons, and the ambassador model 18:22 — Standardization vs. innovation: is the design system the right place for innovation? 19:34 — Reframing the idea: "the system enables product teams to innovate" and the danger of generic innovation mandates 21:16 — Working with
- Episode 069 Deep Dive: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimaa HassanMar 2, 2026 · 55 minEpisode 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 production. Ben surveyed 1,061 design system practitioners and received 53 responses across four questions: a 0–5 range question asking how often respondents think about throwing their system away and starting over, plus three open-text questions — (1) what's the one decision you'd make differently on day one, (2) how do you keep product teams confident in a system being rebuilt underneath them, and (3) share a story about rebuilding mid-flight. Key themes include token architecture, composability, governance, and the honest reality of how rarely formal migration mandates get enforced. --- Show Notes - 00:02 — Welcome and intro - 00:27 — Shimaa's background: from Alexandria, Egypt to design systems at Square and Remote - 02:28 — Shimaa's current challenge: rebuilding at Remote while the product ships continuously - 04:46 — Survey methodology and overview of the four questions - 05:43 — Question 1 results: roughly 50/50 split; Ben's sentiment analysis of the extremes - 08:48 — Question 2 highlights: token architecture, simplicity, composability, governance, leading with documentation - 10:09 — Erin on a cross-platform parity audit (iOS, Android, web) and handling breaking changes - 11:36 — Shimaa on balancing live product state with new system decisions - 12:37 — Guy on semantic versioning: one major release per year, advance communication, and a CLI tool that automated 70% of breaking change migrations - 14:34 — Taylor on SLAs, defining "breaking change" for your system vs. the org, mono repo vs. component-level versioning - 17:45 — Maintaining parallel systems: running old and new simultaneously - 18:53 — Peter references Kim Williams' Clarity talk on managing system transitions - 22:36 — How do you get teams to actually switch? Selling the value of migration - 26:26 — Shimaa's pro tip: run the codebase locally; use AI to audit token usage and map point-A-to-point-B - 29:16 — Guy on mandates that exist on paper but aren't enforced; lower org maturity can work in your favor - 31:41 — Taylor on the system as a place of stability; introducing an "additive threshold" for governance - 36:50 — Shimaa on triage logs tagged "approved / will not do / future" - 38:19 — Peter on adaptable (not rigid) infrastructure; wanting early involvement with consuming teams - 42:07 — Taylor's feature status Airtable for centralizing and communicating request progress - 45:46 — Shimaa introduces Norma Labs: a space for ideas not yet mature eno
- Episode 068 Part II Deep Dive: Design Systems as AI Context with Ben Callahan and TJ PitreFeb 22, 2026 · 54 minEpisode 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 exploration of the challenges that emerge when stochastic models try to keep the deterministic promises of a design system. This week the question turned practical: what work needs to happen behind the scenes so your design system can serve as powerful, reliable AI context? Ben and TJ sent the question to 1,031 design system practitioners and received 184 responses. The community came ready to share—from MCP servers as structured sources of truth, to agentic feedback loops that validate component output against documentation, to honest debate about where Storybook fits in an AI-native workflow. Show Notes 00:00 — Welcome; Ben sets context for the Part II deep-dive format 00:25 — TJ introduces Southleft and his team's focus on AI + design systems 04:00 — Opening the question: where does your design system live as AI context? 09:07 — Design System Assistant MCP vs. Claude Code-to-Figma: which is better for whom? 10:02 — "Vibe coding" and the emerging pattern of going from code → Figma for UI refinement 15:42 — Community discussion: single source of truth vs. federated systems 15:56 — Eric Steinborn: their source of truth spans JS docs, JSON tokens, Figma, a reference site, and Storybook — and the consolidation effort underway 19:57 — TJ's agentic feedback loop: docs → MCP → code generation → screenshot → validation → iteration 22:56 — Ismail Hamila's AI audit agent: agnostic formats, skills, and checking correct variable intent (not just correct variable usage) 31:18 — Orchestration layers, RAG, and vector databases as an alternative to forcing a single source of truth 31:45 — Ismail's cautionary tale: burning $10 of tokens on a poorly-architected first agent run 34:04 — FigJam spotlight: NY State team's pattern engine; Jennie Yip's design system as AI infrastructure diagram 44:12 — Where does Storybook fit? TJ makes the case for Storybook MCP (via Chromatic) depending on your team 45:35 — Jennie Yip: how packaging everything into an MCP server eliminated AI hallucination 48:04 — Kevin Muldoon in chat: "The blueprint is not derived from the building. Authority flows from origin, not from output." 50:46 — Wrap-up and gratitude for FigJam participation 54:04 — Ben's closing: raw data, FigJam, and coaching resources at https://bencallahan.com Where to Find the Hosts Ben Callahan is the founder of Sparkbox ( https://sparkbox.com ) and the Redwood
- Episode 68 Deep Dive: Design Systems as AI Context with Ben Callahan & TJ PitreFeb 16, 2026 · 55 minEpisode 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 practitioners and received 148 responses. The questions explored: How prepared design systems are to act as reliable AI context Whether teams are experimenting with AI-generated UI How practitioners feel about the output—or what’s holding them back What followed was a nuanced, honest conversation about infrastructure, documentation, design-to-dev parity, and the emotional tension many practitioners feel in this moment. Show Notes 00:00 – Introduction & Topic Framing Design systems as AI context and acknowledging the tension around AI. 06:38 – Survey Overview & Readiness Data Why most teams feel underprepared—and why that matters. 11:51 – Experimentation vs. Confidence Many are testing AI even if they don’t feel ready. 13:17 – What Does “AI Readiness” Actually Mean? The gap between perceived readiness and actual infrastructure maturity. 14:14 – Figma as Canonical Source of Truth How context cascades from design to development—and where it breaks. 16:11 – The Figma Bridge Experiment Using APIs to extract component specs and generate code with AI. 17:05 – Discovering the Cracks Detached components, hard-coded values, missing properties, and hidden inconsistencies. 20:18 – “Infrastructure Wins Over Prompting” Why better prompting isn’t the answer—better system architecture is. 22:30 – Beyond Visual Fidelity Metadata, ARIA labels, intent, and behavior as critical AI context. 24:44 – Documentation Drift & Context Sprawl AI can’t distinguish outdated documentation without human governance. 29:25 – Design-to-Dev Parity Workflows Using tooling to compare canonical sources and surface deviations automatically. 32:57 – AI as Passenger, Not Driver Key Themes 1. Infrastructure > Prompting The quality of AI output is directly tied to the integrity of your system. If your components are inconsistent, disconnected, or poorly documented, AI will expose those cracks—not fix them. 2. Context is the New Prompt 2024 was about prompts. 2025 is about context. Systems that encode intent, behavior, accessibility, and relationships between components will outperform purely visual librarie
- Episode 68 Recap: Design Systems as AI Context with Ben Callahan & TJ PitreFeb 16, 2026 · 30 minEpisode 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 responses. The questions explored how prepared design systems are to act as reliable AI context today, whether practitioners have experimented with AI-generated UI from their design systems, and how they feel about the output (or what's keeping them from trying). The conversation that follows is a recap of the deep dive into the emerging relationship between design systems and AI, revealing why infrastructure and context quality matter more than clever prompts when it comes to AI-assisted workflows. --- Show Notes 00:00 - Introduction & Welcome 02:10 - Survey Overview & The Emotional Landscape of AI 03:27 - The Three Survey Questions 04:41 - Perception vs. Reality of AI Readiness 06:34 - Detached Components and Hidden Cracks 08:40 - AI Slop as a Signal for System Quality 09:32 - Can AI Eventually Infer Intent Without Clean Context? 11:09 - The Case for Human Involvement and Original Thought 13:31 - Compounding Slop: When AI Builds on Its Own Mistakes 14:28 - Context Engineering vs. Vibe Coding 15:06 - Evals: Having Your AI Check Your AI 17:48 - The Russian Doll Method: Building Systems Atomically 20:04 - Human Oversight in the AI Workflow Loop 20:44 - Infrastructure Wins Over Prompting 22:37 - Tools: Serena MCP and Sequential Thinking 23:56 - Closing Advice: Stay Curious, Start Small 25:42 - Getting Started: Claude Chat + Figma MCP 27:37 - The Most Impactful Change: Run Diagnostics on Your System 29:29 - Closing Reflections & What's Next --- Resources Mentioned - TJ's AI and Design Systems course: (https://https://aianddesign.systems//) - Serena MCP: https://github.com/oraios/serena - Sequential Thinking MCP: https://github.com/modelcontextprotocol/servers/tree/main/src/sequentialthinking Where to Find the Hosts **TJ Pitre**: Founder of South Left, creator of Figma Console MCP, and educator on AI and design systems. Known for bridging the gap between design systems infrastructure and AI-powered workflows. (https://southleft.com/) **Ben Callahan**: Host of The Question, Founder of Redwoods Design System Community and Founder of Sparkbox. (https://bencallahan.com, https://sparkbox.com) Get the Raw Data Access the complete survey data from Episode 068 to conduct your own analysis (https://bit.ly/4apfR5v) Review the FigJam Notes Dig into the collaborative notes we took as a community during the deep dive (ht
- Full: Episode 067 of The Question with Ben Callahan & Yesenia Perez-Cruz on Design Systems that DifferentiateFeb 1, 2026 · 50 minEpisode 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 practitioners to discuss the tension between sameness and differentiation in our consuming products. Ben surveyed 1,027 design system practitioners and received 55 responses exploring three key questions: Where does sameness emerge in products? What's your system's primary goal (efficiency, cohesion, or differentiation)? And what bottleneck most restricts product expression? The conversation reveals the cultural, architectural, and philosophical challenges of building systems that both accelerate and differentiate—featuring perspectives from teams across the world. Show Notes 00:00 - Welcome & Yesenia's Background Ben welcomes participants and introduces Yesenia Perez-Cruz as co-host Yesenia's journey : Started with graphic design education (primarily print, some early Dreamweaver) First job at Happy Cog agency doing responsive websites Early realization: Need to make decisions systematically (not 10 different header styles) 2011 : First article on design systems (describing systematic decision-making process) Agency work delivering "style guides" to clients, early theming work Jose Garces restaurants project : Six distinct restaurant brands requiring systematic brand expression Vox Media : Led design system for eight distinct editorial brands moving to centralized team Shopify/Polaris : Led system that had good adoption but noticed sameness creeping in Point of sale team adopted admin system—felt too similar Mobile team had same issue Focus: How to get diverse expression within huge platform Six years at Shopify, now doing independent design work and consulting 03:14 - The Expression Lens: A Different Approach to Systems Most practitioners enter systems looking for consistency Yesenia's unique lens: Systems can empower/enable expression Consistency is good to an extent , but that extent is often exaggerated Clear inconsistencies can break trust (example: phishing email from your bank) But consistency can delve into a space where "it's not good anymore" The problem : Design solutions aren't actually communicating information when content is flattened Many challenges stem from pushing too hard toward consistency 04:40 - Survey Results
- Recap: Episode 067 of The Question with Ben Callahan & Yesenia Perez-Cruz on Design Systems that DifferentiateFeb 1, 2026 · 26 minEpisode 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 to 1,027 design system practitioners and received 55 responses. The questions explored where sameness emerges in products, what design system teams prioritize as their primary system goal (operational efficiency vs. brand cohesion vs. product differentiation), and what aspect of their design system acts as the biggest bottleneck to product expression. The conversation that follows is a recap of the deep dive into the tension between standardization and innovation, revealing frameworks and strategies for creating design systems that both accelerate and differentiate. --- Show Notes 00:00 - Introduction & Survey Overview Ben welcomes Yesenia Perez-Cruz as co-host for the Episode 067 recap Context: Just finished deep dive with participants reviewing raw data Survey details: 1,027 practitioners contacted, 55 responses received Three questions explored: where sameness emerges, primary system goals, and bottlenecks to expression First question results were evenly split across categories (30-50% for each option) 02:27 - Defining Sameness, Differentiation, and Expression Participants immediately questioned: "Don't we want sameness? Expression defined : Does the interface look like the thing users are doing? Do visual cues communicate content meaning (shipping profiles, order lists, etc.)? Sameness defined : When the shape of components overrides the content—everything looks like generic headers, lists, and footers The key distinction : Good expression means content emerges rather than being hidden by component structure Expression is really just good visual communication and design 04:42 - Did Design Systems Create Sameness? Historical context: Brett Victor's "Magic Ink" article from 2005 identified this problem before design systems existed Victor argued product designers aligned with industrial design (mechanical tools) vs. graphic design (information shaping) He cited "ancestors of design systems" as contributors to sameness Conclusion : Design systems aren't the only cause, but are "the cost of economies of efficiency" The problem predates design systems but has been accelerated by them <st
- Full: Episode 066 of The Question with Ben Callahan & Laura Kalbag on The Design System Learning CurveJan 18, 2026 · 54 minThe 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. Community members share insights on multidisciplinary backgrounds, the value of peers and mentorship, the challenge of articulating shared problems and values across organizations, and the tension between standardization and meeting teams where they are. Introduction to Design Systems (00:00) - Welcome and overview of the episode topic - Ben introduces Laura Kalbag as co-host - Laura's background as designer-developer with accessibility expertise - Early adoption of design systems (writing about them since 2012) - Current work with Penpot on educational materials - Book: Accessibility for Everyone (going free online with audiobook) Exploring the Design System Learning Curve (00:00) - How The Question works: survey format and community participation - 77 responses from 1,025 practitioners - Four key questions about learning and industry standards - First question results: Do you feel qualified? (75% yes, 17% no, 8% other) - Themes: constant references to peers, mentorship, and multidisciplinary backgrounds - Standards question showing nearly even split (yes/no/other) Engaging with the Community: Collaborative Learning (05:16) - Laura's opening question: Where would you tell a new designer to start? - Christine: Point to thought leaders (Brad Frost, Dan Mall, Jina Anne, Nathan Curtis) - Recommendation to work in product/UX roles first before systems - Importance of systems thinking - looking at things holistically - Ismael: Value of product management skills and understanding users - Learning HTML/CSS fundamentals, semantic structure, and inheritance - Laura: HTML as accessible starting point for newcomers Mentorship and Guidance in Design Systems (08:57) - Greg: "The people who see systems are the ones who make them" - Systems thinking as natural progression for some practitioners - Learning from industry leaders but adapting to your specific context - Disclaimer needed: what works for IBM or Spotify may not work for you - Guy: Ask "why" someone wants to get into design systems first - Understanding the process, not just copying outputs - Risk of burnout from always seeing systems and implications - Danger of over-codifying and creating restrictive structures Understanding Your Motivation for Design Systems (17:52) - Different aspects: code, coordination, fame, specific challenges - Tailoring guidance based on individual motivations and goals - Jeremy Keith quote: Design system doc sites are like social media (only show the good)
- Recap: Episode 066 of The Question with Ben Callahan & Laura Kalbag on The Design System Learning CurveJan 16, 2026 · 23 minEpisode 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 newcomers. Topics Imposter syndrome and qualification (00:00-06:12) - Do people feel qualified as design system specialists? - Connection between self-taught learning and lack of confidence - Systems thinkers: "The people who see systems are the ones who make them" Learning paths and skills development (06:12-09:00) - How practitioners learned: scrappy, experimental, self-taught - Value of working in other roles first (product design, development, product management) - Design systems as increasingly broad field requiring specialization Systems thinking benefits and challenges (07:23-09:00) - Risk of burnout from always seeing systems - Danger of over-codifying and creating restrictive structures - Managing your systems brain Community learning and resources (16:39-20:52) - Challenge of finding good information amid AI-generated content - Value of human connection and community curation - Potential for gathering trusted resources rather than top-down standards Academic vs. practical preparation (16:39-18:28) - Gap between art school confidence and professional readiness - Sparkbox's apprenticeship program: paid 6-month positions to bridge the gap - Creating materials for professional practice, not just theory AI's impact on learning and entry positions (18:28-19:54) - Difficulty finding trustworthy information - Machines talking to machines with no human wisdom - Entry-level positions being impacted The unique moment we're in (21:46-22:34) - Early design system practitioners now in leadership roles - Potential for more fertile soil with leaders who understand the work - Question: how do we build the pipeline? Standardization and community resources (21:04-21:46) - Building on existing HTML patterns - Brad Frost's global design system concept - Component galleries and shared understanding Resources - Recap of Episode 055 with Lauren LoPrete on Managing your Systems Brain - To Be a Leader of Systems by Hazel Weakly - Ben on LinkedIn - Laura on LinkedIn - Get The Question in your Inbox - Redwoods Design System Community