The Question: Design System Collaborative Learning

Episode 069 Recap: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimaa Hassan
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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.
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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 product teams: how to collaborate on patterns that are ready to be standardized
22:13 — Closing thoughts and wrap-up
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Where to Find the Hosts
Ben 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/
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Get the Raw Data
Access the complete survey data from Episode 069 to conduct your own analysis: https://bit.ly/46s0G9w
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Review the FigJam Notes
Dig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4aNvT8j
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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

Episode 069 Deep Dive: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimaa Hassan
Introduction
In episode 069 of *The Question*, host Ben Callahan (founder of Sparkbox and the Redwoods Design System Community) sits down with co-host Shimaa Hassan to tackle one of the most universal challenges in the space: rebuilding a design system while the products it supports are still in 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.
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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
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Resources Mentioned
- Kim Williams' Clarity Conference talk on transitioning between design systems (https://designsystems.media/video/kim-williams-start-with-your-brand-purpose/)
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Where to Find the Hosts
Ben 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/
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Get the Raw Data
Access the complete survey data from Episode 069 to conduct your own analysis: https://bit.ly/46s0G9w
---
Review the FigJam Notes
Dig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4aNvT8j
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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

Episode 068 Part II Deep Dive: Design Systems as AI Context with TJ Pitre
Aired live: February 20, 2026
Introduction
In Part II of Episode 068, host Ben Callahan is joined again by co-host TJ Pitre—founder of Southleft, a front-end design development agency specializing in the intersection of AI and design systems—for a live community deep dive. This episode builds on Episode 068 Part I's 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 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 Data
Access the survey data for this episode here: https://bit.ly/4apfR5v
Review the FigJam Notes
Community notes from the deep dive: https://bit.ly/4c9cvFp
Join the Conversation
Subscribe to The Question and join the Redwoods community at https://bencallahan.com/thequestion.

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 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 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.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: 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

Episode 068 Recap: Design Systems as AI Context with Ben Callahan & TJ Pitre

Introduction
Welcome to The Question Episode 068 Recap. In this episode, Ben Callahan sits down with TJ Pitre—founder of South Left studio—to unpack the results from this week's survey on design systems as AI context.
Ben sent the three-question survey to 1,031 design system practitioners and received a record 148 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.
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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
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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 (https://bit.ly/4c9cvFp)
Join the Conversation
The 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)