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

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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