The Question: Design System Collaborative Learning

Episode 073 Recap: Design System AI Automation with Ben Callahan and Davy Fung
Host Ben Callahan and co-host Davy Fung, a product designer on the Atlassian Design System and host of the Design System Office Hours podcast, sit down immediately following the Episode 073 deep dive to reflect on what they heard from the community. The survey was sent to 1,077 design system practitioners and received 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 average; craft is rising above it"
25:21 - Thanks and outro
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
Davy Fung is a Product Designer on the Atlassian Design System and host of the Design System Office Hours podcast (https://bit.ly/3AQYjjI). Connect with him on LinkedIn (https://bit.ly/3XrcF2W).
Get the Raw Data
Access the complete survey data from Episode 073 to conduct your own analysis: https://bit.ly/4cIjAv8
Review the FigJam Notes
Dig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4tW5ZHA
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 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, systems thinking, and human judgment
43:00 - The V0/AI coding tool support burden falling unexpectedly on design system teams
45:02 - Community as the antidote to feeling overwhelmed by tooling change
45:31 - Doug's question: how to expose design documentation to AI via MCP
46:29 - Davy's answer: Atlassian's JSON-structured content powering their ADS MCP
47:28 - Closing reflections; encouragement to dig into Q4 raw answers on craft
47:55 - Community updates: Redwoods writing accountability group, Guy's "Cost of Yes" article
48:51 - Upcoming events: Zeroheight Converge in Newcastle (October), UX London (June, code: JOIN_BC for 20% off)
49:25 - Outro
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
Davy Fung is a Product Designer on the Atlassian Design System and host of the Design System Office Hours podcast (https://bit.ly/3AQYjjI). Connect with him on LinkedIn (https://bit.ly/3XrcF2W).
Get the Raw Data
Access the complete survey data from Episode 073 to conduct your own analysis: https://bit.ly/4cIjAv8
Review the FigJam Notes
Dig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4tW5ZHA
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 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 - Staying connected to product work keeps system teams grounded in consumer reality
27:31 - Mapping stakeholders: identifying high-influence non-advocates and converting them
28:35 - Doug: influence can come from the product, not just the person
29:57 - AI in design system support: useful for self-service, but reduce touch points with caution
31:01 - Closing reflections and thanks
31:39 - Outro
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
Doug Neiner is a Principal Software Engineer at Planview. Connect with him on LinkedIn.

Get the Raw Data
Access the complete survey data from Episode 072 to conduct your own analysis: **https://bit.ly/41H6Tf7**

Review the FigJam Notes
Dig into the collaborative notes we took as a community during the deep dive: **https://bit.ly/4mm3uLZ**

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 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: when is high-touch support too much? 
37:19 - Transitioning from high-touch support to self-service empowerment 
43:51 - Live prototyping as a low-effort, high-value support approach 
45:15 - Figma detachable components and slots discussion 
45:50 - Christine's bi-weekly demo program at office hours 
47:56 - Closing reflections; encouragement to read Q4 survey answers 
48:25 - Community updates: Redwoods, Design System Triage, Converge in Newcastle 
50:09 - Outro

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
Doug Neiner is a Principal Software Engineer at Planview. Connect with him on LinkedIn.
Get the Raw Data
Access the complete survey data from Episode 072 to conduct your own analysis: https://bit.ly/41H6Tf7
Review the FigJam Notes
Dig into the collaborative notes we took as a community during the deep dive: https://bit.ly/4mm3uLZ
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 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 the UI
40:06  Ben: FOMO-driven AI adoption decisions
41:32  Taylor: legacy systems are often politically protected
44:15  Ben: systems thinkers evaluated on product KPIs—structural misalignment
46:35  Kele: reframing "healthy tension" as creative friction with different mandates
49:22  Closing and thank-yous
49:48  Redwoods membership, UX London, previous episode with Hannah
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: https://bit.ly/4rYcRTk
Review the FigJam notes
Dig into the collaborative notes from the deep dive: https://bit.ly/4bKWSlt
Join the conversation
Participate in future episodes and contribute to the next survey: https://bit.ly/answerTheQuestion