{"type":"rich","version":"1.0","provider_name":"Transistor","provider_url":"https://transistor.fm","author_name":"The Question: Design System Collaborative Learning","title":"Episode 069 Deep Dive: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimaa Hassan","html":"","width":"100%","height":180,"duration":3321,"description":"Episode 069 Deep Dive: Rebuilding a Design System Mid-Flight with Ben Callahan & Shimaa HassanIntroductionIn 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...","thumbnail_url":"https://img.transistorcdn.com/8ZoZhDyVederAFF-YGuNFdyaUvqzao3a6rYS6VFp3F4/rs:fill:0:0:1/w:400/h:400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9kMjQ2/MjJjYzdiYmY4MWU0/NGQzMjJmOGUyNzlj/YmMwZS5wbmc.webp","thumbnail_width":300,"thumbnail_height":300}