The Question: Design System Collaborative Learning

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 ❤️

Episodes

  1. Episode 070 Deep Dive: Lasting Design System Infrastructure with Ben Callahan & Hannah Clarke

    2 DAYS AGO

    Episode 070 Deep Dive: Lasting Design System Infrastructure with Ben Callahan & Hannah Clarke

    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 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 collaboration 30:54 — Hannah: The full-stack cycle — companies oscillate between specialists and generalists at their own peril 32:23 — Greg: Flipping the unicorn question — even if unicorns existed, would they want to do everything expected of them? 36:05 — Amy: Designers vibe coding directly in repos; how design systems can support that workflow and reduce chaos 37:31 — Joanna: Built two full implementations (React + Angular) after teams refused a framework-agnostic approach; the real costs 39:30 — Sean: Extending across iOS + Android; shared tokens, consistent naming, cross-platform rituals; treating Figma as a fourth platform 41:22 — Managing cross-platform parity: Manual processes, shared style layers, prioritization by demand 44:09 — Hannah: Why she moved away from "just React" thinking; the unsolved mobile challenge for a three-person team 46:36 — API flexibility vs. rigidity: Joanna's case for flexible APIs; Hannah and Mike on finding the balance without losing consistency 51:01 — Closing remarks and community announcements Where to Find the Hosts Ben Callahan, Founder of Sparkbox and Redwoods Design System Community: https://bencallahan.com Hannah Clarke, UI Engineer at Intapp: https://bit.ly/47kl2ln Get the Raw Data: https://bit.ly/3OOuU0B Review the FigJam Notes: https://bit.ly/4rxa9E8 Join the Conversation: https://bit.ly/answerTheQuestion

    53 min
  2. Episode 070 Recap: Lasting Design System Infrastructure with Ben Callahan & Hannah Clarke

    2 DAYS AGO · BONUS

    Episode 070 Recap: Lasting Design System Infrastructure with Ben Callahan & Hannah Clarke

    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 for 50% off Pro for 6 months) IntroductionIn 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 Notes00:00 — Welcome & sponsor mention (Mintlify)00:45 — Survey methodology recap: 1,061 sent, 45 responses, four questions reviewed01:20 — Q1 results: Company leadership — "led by product" dominated; why that surprised Ben but not Hannah02:35 — 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 hosts05:35 — Job posting trends: Why available design system roles skew toward design over engineering06:49 — The unicorn problem: Companies asking for one person to do it all07:20 — 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 matter09:10 — 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 tooling11:36 — Data note: Over 60% of Q4 responses mentioned humans, people, community, champions, or trust12:22 — The cultural hurdle: Solving a technical problem doesn't mean people will adopt it13:13 — Framework agnostic vs. framework-specific: Three respondents advocated for agnosticism; Joanna's team built two separate libraries14:08 — Hannah's approach at Intapp: Why they chose Stencil + web components and the longevity thinking behind it15:43 — How they actually deliver components: NPM packages for tokens, styles, web components, React 18, and React 19/SSR18:49 — Post-processing scripts on top of Stencil: Default values, required props, types files, and developer quality-of-life improvements20:26 — Lowering the barrier to adoption: Making it painless for consuming teams to say yes21:38 — Working with teams already using Material UI: Not replacing everything, but filling the gaps24:07 — What does DevOps actually mean on a design system team day-to-day?26:14 — Hannah's surprising reality: Nearly 100% of her time is infrastructure, not component-building28:04 — Design-side agnosticism: Is Figma-lock sustainable? What Guy's team is doing differently29:30 — Treating Figma as a platform (alongside iOS, Android, web) — a mindset for longevity30:16 — Documentation-driven implementation: Defining the component as data first, then expressing it in any tool31:23 — Closing thought: Systems that last are defined above the tools, not inside them Where to Find the HostsBen 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 Hannah Clarke is a UI Engineer at Intapp. Connect with her on LinkedIn: https://bit.ly/47kl2ln Get the Raw DataAccess the complete survey data from Episode 070 to conduct your own analysis: https://bit.ly/3OOuU0B Review the FigJam NotesDig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4rxa9E8 Join the ConversationThe Question explores design systems topics through community research and deep-dive discussions. Participate in future episodes and contribute to the next survey: https://bit.ly/answerTheQuestion

    32 min
  3. Episode 069 Recap: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimma Hassan

    2 MAR · BONUS

    Episode 069 Recap: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimma Hassan

    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 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 Notes0:05 — Introductions: Ben welcomes Shimaa Hassan as co-host for episode 690:18 — Episode context: rebuilding a design system mid-flight and how Ben and Shimaa connected1:00 — Survey recap: the "how often do you think about starting over?" question and why Shimaa expected a higher number1:36 — Data results: the ~50/50 split and overview of the three open-text survey questions2:30 — The "fork and maintain" approach: letting teams use the old version while building the new one3:19 — Shimaa's iterative approach: design rebuilt from scratch, engineering making incremental changes in code4:53 — Step-by-step walkthrough: how Shimaa used the existing codebase and AI tools to inform the new architecture7:29 — Systematizing what already exists: abstracting and naming tokens vs. inventing new ones8:10 — Avoiding breaking changes: the strategy of supporting the live state while layering in improvements9:29 — Finding the middle ground: honoring existing design before driving further evolution10:30 — Multiple versions vs. iterative: Guy's semantic versioning approach vs. smaller teams who can't maintain parallel systems13:30 — Taylor's poll: how few teams have actually had a formal, mandated migration period15:00 — A model for splitting system team responsibilities: dedicated evolution vs. embedded implementation support16:12 — Shimaa's experience at Square: rotation embeds and borrowing engineers between teams17:15 — Empathy building through team exchange programs: pros, cons, and the ambassador model18:22 — 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 mandates21:16 — Working with product teams: how to collaborate on patterns that are ready to be standardized22:13 — Closing thoughts and wrap-up --- Where to Find the HostsBen Callahan—Founder of Sparkbox and the Redwoods Design System Community. Individual and team coaching for design system programs. https://bencallahan.com Shimaa Hassan—Senior Product Designer at Remote, specializing in design systems. https://www.linkedin.com/in/shimaahassan/ --- Get the Raw DataAccess the complete survey data from Episode 069 to conduct your own analysis: https://bit.ly/46s0G9w --- Review the FigJam NotesDig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4aNvT8j --- Join the ConversationThe Question explores design systems topics through community research and deep-dive discussions. Participate in future episodes and contribute to the next survey: https://bit.ly/answerTheQuestion

    23 min
  4. Episode 069 Deep Dive: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimaa Hassan

    2 MAR

    Episode 069 Deep Dive: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimaa Hassan

    Episode 069 Deep Dive: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimaa Hassan IntroductionIn 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 enough for the core system- 47:06 — Aaron on component-level versioning with 20 components needing updates simultaneously- 48:30 — Tallulah and Liz on capacity constraints; offering support windows to encourage faster migration- 50:45 — Liz on her IBM experience building testing infrastructure to keep React and Angular in parity- 52:31 — Peter's closing mantra: "Don't show me different, show me better"- 53:01 — Shimaa's closing reflection; Ben's announcements --- Resources Mentioned- Kim Williams' Clarity Conference talk on transitioning between design systems (https://designsystems.media/video/kim-williams-start-with-your-brand-purpose/) --- Where to Find the HostsBen Callahan—Founder of Sparkbox and the Redwoods Design System Community. Individual and team coaching for design system programs. https://bencallahan.com Shimaa Hassan—Senior Product Designer at Remote, specializing in design systems. https://www.linkedin.com/in/shimaahassan/ --- Get the Raw DataAccess the complete survey data from Episode 069 to conduct your own analysis: https://bit.ly/46s0G9w --- Review the FigJam NotesDig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4aNvT8j --- Join the ConversationThe Question explores design systems topics through community research and deep-dive discussions. Participate in future episodes and contribute to the next survey: https://bit.ly/answerTheQuestion

    55 min
  5. Episode 068 Part II Deep Dive: Design Systems as AI Context with Ben Callahan and TJ Pitre

    22 FEB

    Episode 068 Part II Deep Dive: Design Systems as AI Context with Ben Callahan and TJ Pitre

    Episode 068 Part II Deep Dive: Design Systems as AI Context with TJ PitreAired live: February 20, 2026 IntroductionIn 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 Notes00:00 — Welcome; Ben sets context for the Part II deep-dive format00:25 — TJ introduces Southleft and his team's focus on AI + design systems04:00 — 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 refinement15:42 — Community discussion: single source of truth vs. federated systems15:56 — Eric Steinborn: their source of truth spans JS docs, JSON tokens, Figma, a reference site, and Storybook — and the consolidation effort underway19:57 — TJ's agentic feedback loop: docs → MCP → code generation → screenshot → validation → iteration22:56 — 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 truth31:45 — Ismail's cautionary tale: burning $10 of tokens on a poorly-architected first agent run34:04 — FigJam spotlight: NY State team's pattern engine; Jennie Yip's design system as AI infrastructure diagram44:12 — Where does Storybook fit? TJ makes the case for Storybook MCP (via Chromatic) depending on your team45:35 — Jennie Yip: how packaging everything into an MCP server eliminated AI hallucination48:04 — 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 participation54:04 — Ben's closing: raw data, FigJam, and coaching resources at https://bencallahan.com Where to Find the HostsBen Callahan is the founder of Sparkbox (https://sparkbox.com) and the Redwoods Design System Community (bencallahan.com/redwoods), and host of The Question (https://bencallahan.com/the-question). Find him on LinkedIn (https://bit.ly/3T6rd5S). TJ Pitre is the founder of Southleft (https://southleft.com/). Find TJ on LinkedIn (https://bit.ly/4rsXOBf). Get the Raw DataAccess the survey data for this episode here: https://bit.ly/4apfR5v Review the FigJam NotesCommunity notes from the deep dive: https://bit.ly/4c9cvFp Join the ConversationSubscribe to The Question and join the Redwoods community at https://bencallahan.com/thequestion.

    55 min
  6. Episode 68 Deep Dive: Design Systems as AI Context with Ben Callahan & TJ Pitre

    16 FEB

    Episode 68 Deep Dive: Design Systems as AI Context with Ben Callahan & TJ Pitre

    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 practitioners and received 148 responses. The questions explored: How prepared design systems are to act as reliable AI contextWhether teams are experimenting with AI-generated UIHow practitioners feel about the output—or what’s holding them backWhat 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 FramingDesign systems as AI context and acknowledging the tension around AI. 06:38 – Survey Overview & Readiness DataWhy most teams feel underprepared—and why that matters. 11:51 – Experimentation vs. ConfidenceMany 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 TruthHow context cascades from design to development—and where it breaks. 16:11 – The Figma Bridge ExperimentUsing APIs to extract component specs and generate code with AI. 17:05 – Discovering the CracksDetached 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 FidelityMetadata, ARIA labels, intent, and behavior as critical AI context. 24:44 – Documentation Drift & Context SprawlAI can’t distinguish outdated documentation without human governance. 29:25 – Design-to-Dev Parity WorkflowsUsing 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 libraries. 3. AI Reveals Design Debt Detached components, missing properties, undocumented variants—AI makes hidden system debt visible. 4. Documentation Is a Living System Outdated Confluence pages and static decks become liabilities when surfaced through LLMs. Human oversight and governance remain essential. 5. AI Should Be Embedded in Workflow Not “set it and forget it.” Involve AI throughout design, parity checks, and documentation—not just at the end. Where to Find the Hosts TJ Pitre: Founder of Southleft and working at the intersection of design systems and AI.https://southleft.com/Ben Callahan: Host of The Question, Founder of Redwoods Design System Community and Founder of Sparkbox.https://bencallahan.comhttps://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 notesDig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4c9cvFp Join the Conversation The Question explores design systems topics through community research and deep-dive discussions. Participate in future episodes and contribute to the next survey: https://bit.ly/answerTheQuestion

    55 min
  7. Episode 68 Recap: Design Systems as AI Context with Ben Callahan & TJ Pitre

    16 FEB · BONUS

    Episode 68 Recap: Design Systems as AI Context with Ben Callahan & TJ Pitre

    Episode 068 Recap: Design Systems as AI Context with Ben Callahan & TJ PitreIntroductionWelcome 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 Notes00:00 - Introduction & Welcome02:10 - Survey Overview & The Emotional Landscape of AI03:27 - The Three Survey Questions04:41 - Perception vs. Reality of AI Readiness06:34 - Detached Components and Hidden Cracks08:40 - AI Slop as a Signal for System Quality09:32 - Can AI Eventually Infer Intent Without Clean Context?11:09 - The Case for Human Involvement and Original Thought13:31 - Compounding Slop: When AI Builds on Its Own Mistakes14:28 - Context Engineering vs. Vibe Coding15:06 - Evals: Having Your AI Check Your AI17:48 - The Russian Doll Method: Building Systems Atomically20:04 - Human Oversight in the AI Workflow Loop20:44 - Infrastructure Wins Over Prompting22:37 - Tools: Serena MCP and Sequential Thinking23:56 - Closing Advice: Stay Curious, Start Small25:42 - Getting Started: Claude Chat + Figma MCP27:37 - The Most Impactful Change: Run Diagnostics on Your System29:29 - 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 DataAccess the complete survey data from Episode 068 to conduct your own analysis (https://bit.ly/4apfR5v) Review the FigJam NotesDig into the collaborative notes we took as a community during the deep dive (https://bit.ly/4c9cvFp) Join the ConversationThe Question explores design systems topics through community research and deep-dive discussions. Visit the show website to participate in future episodes and join the conversation. (https://bit.ly/answerTheQuestion)

    30 min
  8. Full: Episode 067 of The Question with Ben Callahan & Yesenia Perez-Cruz on Design Systems that Differentiate

    1 FEB

    Full: Episode 067 of The Question with Ben Callahan & Yesenia Perez-Cruz on Design Systems that Differentiate

    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 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-hostYesenia's journey: Started with graphic design education (primarily print, some early Dreamweaver)First job at Happy Cog agency doing responsive websitesEarly 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 workJose Garces restaurants project: Six distinct restaurant brands requiring systematic brand expressionVox Media: Led design system for eight distinct editorial brands moving to centralized teamShopify/Polaris: Led system that had good adoption but noticed sameness creeping in Point of sale team adopted admin system—felt too similarMobile team had same issueFocus: How to get diverse expression within huge platformSix years at Shopify, now doing independent design work and consulting03:14 - The Expression Lens: A Different Approach to Systems Most practitioners enter systems looking for consistencyYesenia's unique lens: Systems can empower/enable expressionConsistency is good to an extent, but that extent is often exaggeratedClear 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 flattenedMany challenges stem from pushing too hard toward consistency04:40 - Survey Results Overview Question 1: Where do you notice sameness emerging? Overall layout and page structureVisual hierarchy and emphasisInteraction patterns and behaviorsBrand expression and personality"I don't notice meaningful sameness"Results: Fairly even distribution (30-50% each)Very few people (5-6) said they don't notice samenessFollow-up question posted: For those who don't notice sameness, what's unique about your architecture or processes?Question 2: Primary goal of your system? About half: Operational efficiencyOthers: Brand cohesionSmaller group: Product differentiationObservation: Most teams want both efficiency AND cohesionForcing choice to primary goal revealed interesting tensionsQuestion 3: Open-ended responses about bottlenecks Component flexibilityToken structuresDocumentation (big theme)Decision paralysis (surprising theme)09:24 - Decision Paralysis and Designer Safety Key insight: Best design work happens when designers are relaxed, having fun, in flow stateWhen you don't know the bounds you can work within, you tense up"Can I put this line here? Can I use this color background? Will I get in trouble?"Result: Retreat to what feels safe—copying what's already approvedLack of clarity about permissions takes away the safety of designNot about sacrificing brand expression for consistency—need to solve this tensionKnowing the bounds enables creative problem-solving with the design language12:13 - Stephen: AI and Design Systems Parallel Working with AI recently reveals similar challengesAI "does whatever it can to not follow the rules"Explores areas where documentation doesn't quite forbid somethingSame question: Where are proper constraints vs. room for creative exploration?How do companies prioritize tasks for AI (needing explicit boundaries) vs. humans?Yesenia's response: Design language as a tool for creative freedom can be liberatingHumans have judgment to assess "is this working well?" that AI currently lacksNeed to meet both ends of the spectrum14:09 - Kaelig's Comment: "Everything Looking the Same Is Good" Chat comment challenges fundamental assumptionYesenia's response: There are phases to design systems Typically start wanting convergence—reducing too much variationThis is absolutely validThe problem: How to get convergence without getting stuck in placeFive years ago problem: If you created a system 5 years ago, you're converging on how the product existed thenNeed ability to move from thereExpression clarification: Doesn't necessarily mean brand personality Core question: Does the thing you're using look like the action you're taking?Mac example: Control Center (big affordances for quick actions) vs. System Settings (tiny controls, explanatory text)Spectrum of UI tailored for specific tasksExpression is about appropriateness to context and content16:33 - Matt (New York Times): Typography, Culture, and Letting Go NYT designers are very particular about typographyPrevious systems were strict: "text-small, text-medium, text-large"Stakeholder requests: "I want 15 [pixels]"Matt's evolution: Trying to let go of rigid rulesOpportunity: When you let go, the culture of the design org can come outTension: Also creates room for chaosQuestion: How do you give up design system control and give control to customers?How do teams manage based on org culture?17:44 - Layers: Tokens, Components, Composition Yesenia's framework: Push as far as possible at compositional layer before changing token layerCan do something more powerful at composition than at token levelPromo card example: Team wants new color token for "promo"Yesenia pushes back: What's more powerful to indicate promotion?Uber Eats reference: Promo card looks like actual coupon—different z-index, inset notchesMuch stronger visual representationDecision criteria: Pus...

    50 min
  9. Recap: Episode 067 of The Question with Ben Callahan & Yesenia Perez-Cruz on Design Systems that Differentiate

    1 FEB · BONUS

    Recap: Episode 067 of The Question with Ben Callahan & Yesenia Perez-Cruz on Design Systems that Differentiate

    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 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 recapContext: Just finished deep dive with participants reviewing raw dataSurvey details: 1,027 practitioners contacted, 55 responses receivedThree questions explored: where sameness emerges, primary system goals, and bottlenecks to expressionFirst 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 footersThe key distinction: Good expression means content emerges rather than being hidden by component structureExpression 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 existedVictor argued product designers aligned with industrial design (mechanical tools) vs. graphic design (information shaping)He cited "ancestors of design systems" as contributors to samenessConclusion: 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 06:50 - Drift vs. Differentiation: Critical Distinctions Drift: When things that are the same look different (unintentional inconsistency)Example: Delete actions using different icons (X vs. trash can)Users shouldn't have to relearn patterns for the same actionDifferentiation: When things that are different look appropriately differentThings should look like what they are, not all the sameSameness: The opposite of drift—when things that are different look the sameDifferentiation serves both interface clarity AND market positioning 08:10 - Brand Differentiation Through Primitive Components Two meanings of differentiation: interface clarity and market positioningMyMind example: Bookmarking tool with atmospheric, circular brandingReimagined drop zone with circular shapes and soothing animationsStandard components (drop zone, color picker) styled to brand essenceMany teams start by referencing other design systems or galleriesKey insight: For core parts of your experience, create distinct patterns that feel specific to your product 10:37 - Balancing Usability and Expression The usability concern: Familiarity breeds instinctual understandingJacob's Law: Users prefer patterns they're familiar with from other sitesThe nuance: There's space for differentiation in domain-specific componentsWhen components are specific to your domain (not just functional), users are more willing to learn something differentThe line between standardization and innovation isn't the same for every organization 12:22 - How to Decide Where to Standardize vs. Innovate First: Understand the role the system plays in your organizationAre you in efficiency mode or innovation mode?This can ebb and flow within the same companySecond: Understand who needs to create expression and whereExample: Polaris serves both third-party developers (who want decisions made) and internal designers (creating new products)Different audiences within the same organization may need different approachesThe person making the choice matters as much as what the choice is 14:35 - Enablement, Safety, and Experimentation Design systems shape the culture of how designers workThe trust paradox: Sometimes teams trust the system too muchYesenia's experience: Encouraging teams to "start with a blank canvas"Goal was to encourage feedback loops of new patterns into the systemCreating psychological safety for designers to explore outside constraintsHow the system team responds to requests shapes whether people feel safe to experiment 17:27 - The Blank Canvas Approach The risk: Standardizing too much, too earlyYesenia's system worked well for building 2016's product, but not for 2020's needsStrategy: Encourage divergence first, then converge on new patternsCan't standardize things that don't exist yetTeams sometimes jump to defining palettes and typography before understanding the productCreative exploration should continue throughout the adoption process, not just at the beginning 19:10 - Seasons of Innovation and Standardization Organizations pendulum between differentiation/innovation and standardizationBoth don't run full steam simultaneously—it's a seasonal shiftExternal factors impact business needs, which impact design approach, which impacts what gets standardizedExample timeline: Knew token layer wasn't ready, encouraged divergence to learn what needed standardizing, then created new token architecture and consolidatedThis required thinking 3+ years in advanceDesign systems practitioners must predict the future (another skill to add to the matrix!) 20:42 - Trust, Responsibility, and Where to Draw the Line One participant's perspective: "I don't tell designers what to do, I trust they know their craft"The challenge: What does trust mean for design debt and tech debt?It's difficult for system practitioners to block product designers' workPro...

    26 min
  10. Full: Episode 066 of The Question with Ben Callahan & Laura Kalbag on The Design System Learning Curve

    18 JAN

    Full: Episode 066 of The Question with Ben Callahan & Laura Kalbag on The Design System Learning Curve

    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. 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) The Unique Nature of Your Design System (18:21)- Austin: Working at Bass Pro Shops vs. big tech companies- Challenge of resources not fitting organizational context- Greg: "Be happy you don't have their problems"- Looking at intricate systems born from problems you don't have- Blessing of not needing those complex solutions- Focus on the problems that are unique to your users Embedding Values in Design Systems (20:12)- Laura: We embed our values in the design systems we create- Risk of copying big tech values that don't align with your mission- Small Technology Foundation example: creating alternatives to big tech- Question: Are you taking on values that don't represent your product? Imposter Syndrome in Design Systems (21:08)- Greg: First time experiencing true imposter syndrome in nearly two decades- Reading industry masters and feeling inadequate- Redwoods community response: appreciate not having their problems- Shift in perspective about own work in the space- Focus on what you can do that's more interesting for your users Identifying Gaps in Design System Learning (24:44)- Christine: Communication between teams as huge blind spot- Building systems with one product in mind defeats the purpose- Style guides vs. true systems serving multiple products- Need for people at all skill levels to share their learning- Missing links in the learning chain- Everyone has responsibility to share what they're learning The Importance of Change Management (26:34)- Yesenia: Change management as biggest success or failure factor- Getting people to change what they're doing- Adapting communication to organizational context- Relationship-driven vs. storytelling-driven organizations- Mismatch in communication styles leads to failure- Book recommendation: Switch by Chip and Dan Heath- Not trained in change management but must do it anyway The People Side of Design Systems (29:32)- Little focus on people side in survey responses- Austin's revelation: "This is about people" shifted everything- Meet people where they're at instead of holding meetings no one attends- Attend their standups and see how design system can help- Laura: Tooling companies dependent on sharp folks doing cultural work- Standards should be about processes for creating systems, not systems themselves Education and Management in Design Systems (32:21)- Austin: Reaching out on LinkedIn begging for mentorship conversations- Learning about program/product manager role for design systems- Convincing organizations to commit to necessary roles- Taylor's meta observation: We're at a maturation point in the field- Early ICs now moving into director/manager/lead roles- Phase two of design systems establishment- Built-in layers of experience we didn't have years ago The Evolution of Design Systems (36:07)- Taylor: Roles and understanding have changed in the ecosystem- Learning paths for different roles (designer to system designer, etc.)- Need for curated resources with markers in time- Annotating when content becomes outdated- Community-led approaches vs. top-down certification- Standards question discussion: W3C-style standards or community curation?- Stephen: Focus on articulating shared problems and values across organizations- Greg: Extending HTML patterns and elevating emerging needs- Component galleries focused on user problems and solutions- Open source templates for education (tokens, variables, theming)- Meeting teams where they are vs. pushing standards- Gratitude for community participation and thoughtful answers Resources- Recap of Episode 055 with Lauren LoPrete on Managing your Systems Brain (https://bit.ly/3HTh89a)- To Be a Leader of Systems by Hazel Weakly (https://hazelweakly.me/blog/to-be-a-leader-of-systems/)- Ben on LinkedIn (https://bit.ly/3T6rd5S)- Laura on LinkedIn (https://bit.ly/4hI9g8v)- Get The Question in your Inbox (https://bit.ly/3U1hdf3)- Redwoods Design System Community (https://bit.ly/44lzHL5)

    55 min
  11. Recap: Episode 066 of The Question with Ben Callahan & Laura Kalbag on The Design System Learning Curve

    16 JAN · BONUS

    Recap: Episode 066 of The Question with Ben Callahan & Laura Kalbag on The Design System Learning Curve

    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 newcomers. TopicsImposter 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

    24 min
  • 11 Episodes

About

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 ❤️

Information

  • Creator
    Ben Callahan
  • Years Active
    2K
  • Episodes
    11
  • Rating
    Clean
  • Copyright
    © Copyright 2026, Learning Mode, LLC
  • Show Website
    The Question: Design System Collaborative Learning
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