The Question: Design System Collaborative Learning

About The Question: Design System Collaborative Learning

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 ❤️

Publisher

Ben Callahan

Category

technology

Language

en

Explicit

No

First episode

16 Jan 2026

Latest episode

23 Sept 2026

Latest episodes

31 episodes in the feed.

1. 

   23 Sept 2026

   Episode 080 Recap: Visualizing Design System Health with Ben Callahan, Robin Di Capua, and Taylor Cashdan

   To celebrate 80 episodes, Ben Callahan is joined by Robin Di Capua and Taylor Cashdan, who built the Redwoods Compass, a self-reflective tool for looking at design system health without grading it. The survey went to 1,118 design system practitioners and received 52 responses to two questions, along with a first-ever homework assignment: a blank spider chart to fill in by instinct. The conversation covers what "health" even means, how the Compass's six categories emerged from Redwoods workshops, why five of those six aren't about the assets themselves, a respondent who realized mid-answer that none of their metrics measured health, and how the Compass keeps all data local. Show Notes 00:02 — Welcome to episode 080 00:15 — Introducing Robin and Taylor 01:58 — The two survey questions and spider chart homework 03:56 — What is design system health? 04:58 — Human health as an analogy 05:25 — No single indicator of health 06:49 — Redwoods action groups and the Compass's origins 07:54 — What the Compass is, and isn't 08:47 — Six categories and the spider chart 10:58 — Collecting charts to find patterns 11:34 — Workshopping the categories with Redwoods 13:08 — Five of six categories aren't about assets 13:56 — Shipping a button five hundred times 15:14 — Nobody wrote "design tokens" on a sticky note 15:45 — Pivoting from readiness to health 16:47 — Tracking change over time 17:14 — A respondent's mid-answer realization 18:43 — Validating the Compass's framing 19:47 — Why intangibles need conversation, not scores 20:50 — One tool among many 21:41 — How the Compass works locally 23:00 — zeroheight's maturity model and next week's panel 24:18 — How to share feedback 25:11 — Closing Where to Find the Hosts Ben Callahan is Founder of Sparkbox (https://sparkbox.com (https://sparkbox.com/)) and Redwoods Design System Community (https://joinredwoods.com (https://joinredwoods.com/)). Read his writings, have him present at your event, or engage with him as a coach or consultant at https://bencallahan.com (https://bencallahan.com/) Robin Di Capua is a designer on the design system team at GetYourGuide in Zurich. Connect with him on LinkedIn: https://bit.ly/3VYboQI (https://bit.ly/3VYboQI) Taylor Cashdan is a design systems practitioner who has worked across enterprise, startup, and consulting teams. Connect with him on LinkedIn: https://bit.ly/4cZhbKq (https://bit.ly/4cZhbKq) Get the Raw Data Access the complete survey data from Episode 080 to conduct your own analysis: https://bit.ly/4c18Fx5 (https://bit.ly/4c18Fx5) Review the FigJam Notes Dig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4wZmHH7 (https://bit.ly/4wZmHH7) 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 (https://bit.ly/answerTheQuestion) Music licensed through Soundstripe. Code: PC5Z0DRTDVMQITVR

2. 

   23 Sept 2026

   Episode 080 Deep Dive: Visualizing Design System Health with Ben Callahan, Robin Di Capua, and Taylor Cashdan

   Ben Callahan is joined by Robin Di Capua and Taylor Cashdan, members of the Redwoods Design System Community who spent nearly a year building the Redwoods Compass. Robin has worked as a designer since 2009, has focused on systems since 2016, and recently joined the design system team at GetYourGuide in Zurich. Taylor has spent six years as a systems practitioner across enterprise, startup, and consulting teams. The survey went to more than 1,100 practitioners and received 52 responses to two questions, plus a spider chart homework assignment. During the session, participants took the Compass live and compared their gut-check charts with its results. The conversation covers voluntary adoption versus mandates, surprising gaps between charts, legacy systems in the public sector, taking the Compass as a team, and where community fits in the framework. Show Notes 00:04 — Welcome and sponsors 01:09 — zeroheight's maturity model and the Redwoods Compass 02:47 — The survey questions and spider chart homework 05:05 — "None tell me whether the programme is healthy" 05:58 — Origin story: from readiness to health 07:25 — The six Compass categories 09:44 — Setting up the FigJam exercise 12:32 — Taking the Compass: Authority 14:55 — Alignment 17:44 — Resource Lifecycle 19:06 — People 21:02 — Investment 21:33 — Infrastructure 23:54 — Defining design system health 24:31 — Voluntary use and fit as health signals 25:28 — Jesse Gardner on resisting a mandate at New York State 27:14 — Comparing spider charts 30:06 — Leo Vogel on ChatGPT's estimate vs. the Compass 30:58 — Mike Polowick on a drastic gap in People 33:34 — Jesse Gardner on legacy sites and public sector funding 34:54 — Taking the Compass as a team 37:43 — System health vs. effectiveness for your product 39:09 — Using divergence to surface expectations 40:35 — "Too busy" as unrecorded health work 41:59 — Jeremy on quick vs. considered answers 44:59 — A memorable survey answer and four acquisitions 45:49 — Mike Polowick on where community fits 48:19 — zeroheight panel and wrap-up Where to Find the Hosts Ben Callahan is Founder of Sparkbox (https://sparkbox.com (https://sparkbox.com)) and Redwoods Design System Community (https://joinredwoods.com (https://joinredwoods.com)). Read his writings, have him present at your event, or engage with him as a coach or consultant at https://bencallahan.com (https://bencallahan.com) Robin Di Capua is a designer on the design system team at GetYourGuide in Zurich. Connect with him on LinkedIn: https://bit.ly/3VYboQI (https://bit.ly/3VYboQI) Taylor Cashdan is a design systems practitioner who has worked across enterprise, startup, and consulting teams. Connect with him on LinkedIn: https://bit.ly/4cZhbKq (https://bit.ly/4cZhbKq) Get the Raw Data Access the complete survey data from Episode 080 to conduct your own analysis: https://bit.ly/4c18Fx5 (https://bit.ly/4c18Fx5) Review the FigJam Notes Dig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4wZmHH7 (https://bit.ly/4wZmHH7) 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 (https://bit.ly/answerTheQuestion)

3. 

   10 Aug 2026

   Episode 079 Recap: The Evolution of Design System Documentation with Ben Callahan and Afyia Smith

   Episode 079 Recap: The Evolution of Design System Documentation with Ben Callahan and Afyia Smith Ben Callahan and Afyia Smith, a content designer and technical writer specializing in design systems, recap what the community said about who owns documentation and where docs are headed now that machines are reading them too. The survey went to more than 1,100 design system practitioners and drew 61 responses across five questions. The conversation covers the shift from prose to structured content, the case for a dedicated documentation owner, the design system knowledge architect role, the DSDS spec work with PJ Onori, and the fourteen respondents who said machines will be the only future readers of their docs. Show Notes 00:00 — Welcome and introductions 00:14 — Black-and-white prints and a giraffe collection 01:00 — Almost 80 episodes, and the first one on docs 01:24 — Survey setup: 1,100 practitioners, 61 responses 02:34 — Afyia answers the open-ended question herself 02:41 — Documentation as a knowledge layer, not just content 03:20 — Focused ownership and just-in-time documentation 04:08 — What docs looked like in the early design system days 04:30 — Bare, scattered, outdated, ungoverned 06:17 — The case for a point person 07:53 — The design system knowledge architect role 08:20 — Coming back a year later to the same mess 11:03 — Question one results: who owns documentation 11:57 — By design or by default? 12:24 — Digging into the 30% who answered "other" 13:36 — Question two: everyone figuring agentic workflows out alone 14:24 — The correlation that wasn't in the data 15:00 — Question three: reporting on agentic workflow success 16:07 — Ownership reveals visibility more than success 17:00 — Machine readable versus machine parsable 17:20 — Surface-level changes versus foundational ones 17:49 — Bad docs surfaced everywhere are still bad docs 18:49 — Working upstream of AI 19:38 — The component schema work with PJ Onori 20:45 — DSDS, doc origin, and metadata as a trust layer 23:32 — Question five: writing for humans, machines, or both 24:48 — What we would lose without human-readable reference sites 26:48 — Why documentation has always been the passion Where to Find the Hosts Ben Callahan is Founder of Sparkbox (https://sparkbox.com) and Redwoods Design System Community (https://bencallahan.com/redwoods). Read his writings, have him present at your event, or engage with him as a coach or consultant at https://bencallahan.com Afyia Smith is a content designer and technical writer focused on design system documentation, governance, and knowledge architecture. Connect with her: https://bit.ly/4vVUhNP Get the Raw Data Access the complete survey data from Episode 079 to conduct your own analysis: https://bit.ly/4yV4JrD Review the FigJam Notes Dig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4gismBZ 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 Music licensed through Soundstripe. Code: C1COHEMFO6L4XE0H

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