Épisodes

  • Full: Episode 067 of The Question with Ben Callahan & Yesenia Perez-Cruz on Design Systems that Differentiate

    Full: Episode 067 of The Question with Ben Callahan & Yesenia Perez-Cruz on Design Systems that Differentiate
    Feb 1 2026
    Episode 067 Deep Dive: Design Systems That DifferentiateIntroductionWelcome to The Question Episode 067 Deep Dive. Host Ben Callahan is joined by Yesenia Perez-Cruz—author of Expressive Design Systems and former design systems leader at Vox Media and Shopify—for an interactive conversation about design systems that differentiate. This session brings together dozens of design systems practitioners to discuss the tension between sameness and differentiation in our consuming products.Ben surveyed 1,027 design system practitioners and received 55 responses exploring three key questions: Where does sameness emerge in products? What's your system's primary goal (efficiency, cohesion, or differentiation)? And what bottleneck most restricts product expression? The conversation reveals the cultural, architectural, and philosophical challenges of building systems that both accelerate and differentiate—featuring perspectives from teams across the world.Show Notes00:00 - Welcome & Yesenia's BackgroundBen welcomes participants and introduces Yesenia Perez-Cruz as co-hostYesenia's journey: Started with graphic design education (primarily print, some early Dreamweaver)First job at Happy Cog agency doing responsive websitesEarly realization: Need to make decisions systematically (not 10 different header styles)2011: First article on design systems (describing systematic decision-making process)Agency work delivering "style guides" to clients, early theming workJose Garces restaurants project: Six distinct restaurant brands requiring systematic brand expressionVox Media: Led design system for eight distinct editorial brands moving to centralized teamShopify/Polaris: Led system that had good adoption but noticed sameness creeping in Point of sale team adopted admin system—felt too similarMobile team had same issueFocus: How to get diverse expression within huge platformSix years at Shopify, now doing independent design work and consulting03:14 - The Expression Lens: A Different Approach to SystemsMost practitioners enter systems looking for consistencyYesenia's unique lens: Systems can empower/enable expressionConsistency is good to an extent, but that extent is often exaggeratedClear inconsistencies can break trust (example: phishing email from your bank)But consistency can delve into a space where "it's not good anymore"The problem: Design solutions aren't actually communicating information when content is flattenedMany challenges stem from pushing too hard toward consistency04:40 - Survey Results OverviewQuestion 1: Where do you notice sameness emerging? Overall layout and page structureVisual hierarchy and emphasisInteraction patterns and behaviorsBrand expression and personality"I don't notice meaningful sameness"Results: Fairly even distribution (30-50% each)Very few people (5-6) said they don't notice samenessFollow-up question posted: For those who don't notice sameness, what's unique about your architecture or processes?Question 2: Primary goal of your system? About half: Operational efficiencyOthers: Brand cohesionSmaller group: Product differentiationObservation: Most teams want both efficiency AND cohesionForcing choice to primary goal revealed interesting tensionsQuestion 3: Open-ended responses about bottlenecks Component flexibilityToken structuresDocumentation (big theme)Decision paralysis (surprising theme)09:24 - Decision Paralysis and Designer SafetyKey insight: Best design work happens when designers are relaxed, having fun, in flow stateWhen you don't know the bounds you can work within, you tense up"Can I put this line here? Can I use this color background? Will I get in trouble?"Result: Retreat to what feels safe—copying what's already approvedLack of clarity about permissions takes away the safety of designNot about sacrificing brand expression for consistency—need to solve this tensionKnowing the bounds enables creative problem-solving with the design language12:13 - Stephen: AI and Design Systems ParallelWorking with AI recently reveals similar challengesAI "does whatever it can to not follow the rules"Explores areas where documentation doesn't quite forbid somethingSame question: Where are proper constraints vs. room for creative exploration?How do companies prioritize tasks for AI (needing explicit boundaries) vs. humans?Yesenia's response: Design language as a tool for creative freedom can be liberatingHumans have judgment to assess "is this working well?" that AI currently lacksNeed to meet both ends of the spectrum14:09 - Kaelig's Comment: "Everything Looking the Same Is Good"Chat comment challenges fundamental assumptionYesenia's response: There are phases to design systems Typically start wanting convergence—reducing too much variationThis is absolutely validThe problem: How to get convergence without getting stuck in placeFive years ago problem: If you created a system 5 years ago, you're converging on how the product existed thenNeed ability to move from ...
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    50 min
  • Recap: Episode 067 of The Question with Ben Callahan & Yesenia Perez-Cruz on Design Systems that Differentiate

    Recap: Episode 067 of The Question with Ben Callahan & Yesenia Perez-Cruz on Design Systems that Differentiate
    Feb 1 2026
    Episode 067 Recap: Design Systems That Differentiate with Ben Callahan and Yesenia Perez-CruzIntroductionWelcome to The Question Episode 067 Recap. In this episode, Ben Callahan sits down with Yesenia Perez-Cruz—author of Expressive Design Systems and design system consultant, to unpack the results from this week's survey on design systems that differentiate.Ben sent the three-question survey to 1,027 design system practitioners and received 55 responses. The questions explored where sameness emerges in products, what design system teams prioritize as their primary system goal (operational efficiency vs. brand cohesion vs. product differentiation), and what aspect of their design system acts as the biggest bottleneck to product expression. The conversation that follows is a recap of the deep dive into the tension between standardization and innovation, revealing frameworks and strategies for creating design systems that both accelerate and differentiate.---Show Notes00:00 - Introduction & Survey OverviewBen welcomes Yesenia Perez-Cruz as co-host for the Episode 067 recapContext: Just finished deep dive with participants reviewing raw dataSurvey details: 1,027 practitioners contacted, 55 responses receivedThree questions explored: where sameness emerges, primary system goals, and bottlenecks to expressionFirst question results were evenly split across categories (30-50% for each option)02:27 - Defining Sameness, Differentiation, and ExpressionParticipants immediately questioned: "Don't we want sameness?Expression defined: Does the interface look like the thing users are doing? Do visual cues communicate content meaning (shipping profiles, order lists, etc.)?Sameness defined: When the shape of components overrides the content—everything looks like generic headers, lists, and footersThe key distinction: Good expression means content emerges rather than being hidden by component structureExpression is really just good visual communication and design04:42 - Did Design Systems Create Sameness?Historical context: Brett Victor's "Magic Ink" article from 2005 identified this problem before design systems existedVictor argued product designers aligned with industrial design (mechanical tools) vs. graphic design (information shaping)He cited "ancestors of design systems" as contributors to samenessConclusion: Design systems aren't the only cause, but are "the cost of economies of efficiency"The problem predates design systems but has been accelerated by them06:50 - Drift vs. Differentiation: Critical DistinctionsDrift: When things that are the same look different (unintentional inconsistency)Example: Delete actions using different icons (X vs. trash can)Users shouldn't have to relearn patterns for the same actionDifferentiation: When things that are different look appropriately differentThings should look like what they are, not all the sameSameness: The opposite of drift—when things that are different look the sameDifferentiation serves both interface clarity AND market positioning08:10 - Brand Differentiation Through Primitive ComponentsTwo meanings of differentiation: interface clarity and market positioningMyMind example: Bookmarking tool with atmospheric, circular brandingReimagined drop zone with circular shapes and soothing animationsStandard components (drop zone, color picker) styled to brand essenceMany teams start by referencing other design systems or galleriesKey insight: For core parts of your experience, create distinct patterns that feel specific to your product10:37 - Balancing Usability and ExpressionThe usability concern: Familiarity breeds instinctual understandingJacob's Law: Users prefer patterns they're familiar with from other sitesThe nuance: There's space for differentiation in domain-specific componentsWhen components are specific to your domain (not just functional), users are more willing to learn something differentThe line between standardization and innovation isn't the same for every organization12:22 - How to Decide Where to Standardize vs. InnovateFirst: Understand the role the system plays in your organizationAre you in efficiency mode or innovation mode?This can ebb and flow within the same companySecond: Understand who needs to create expression and whereExample: Polaris serves both third-party developers (who want decisions made) and internal designers (creating new products)Different audiences within the same organization may need different approachesThe person making the choice matters as much as what the choice is14:35 - Enablement, Safety, and ExperimentationDesign systems shape the culture of how designers workThe trust paradox: Sometimes teams trust the system too muchYesenia's experience: Encouraging teams to "start with a blank canvas"Goal was to encourage feedback loops of new patterns into the systemCreating psychological safety for designers to explore outside constraintsHow the system team responds to requests shapes whether people feel safe to experiment17...
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    26 min
  • Full: Episode 066 of The Question with Ben Callahan & Laura Kalbag on The Design System Learning Curve

    Full: Episode 066 of The Question with Ben Callahan & Laura Kalbag on The Design System Learning Curve
    Jan 18 2026
    The Question Episode 066: The Design System Learning Curve with Ben Callahan & Laura KalbagBen and Laura lead the community through a conversation about how people learn design systems, revealing that 75% feel qualified despite most being self-taught. The discussion explores whether the field needs W3C-style industry standards, with answers nearly evenly split between yes, no, and other. Community members share insights on multidisciplinary backgrounds, the value of peers and mentorship, the challenge of articulating shared problems and values across organizations, and the tension between standardization and meeting teams where they are.Introduction to Design Systems (00:00)- Welcome and overview of the episode topic- Ben introduces Laura Kalbag as co-host- Laura's background as designer-developer with accessibility expertise- Early adoption of design systems (writing about them since 2012)- Current work with Penpot on educational materials- Book: Accessibility for Everyone (going free online with audiobook)Exploring the Design System Learning Curve (00:00)- How The Question works: survey format and community participation- 77 responses from 1,025 practitioners- Four key questions about learning and industry standards- First question results: Do you feel qualified? (75% yes, 17% no, 8% other)- Themes: constant references to peers, mentorship, and multidisciplinary backgrounds- Standards question showing nearly even split (yes/no/other)Engaging with the Community: Collaborative Learning (05:16)- Laura's opening question: Where would you tell a new designer to start?- Christine: Point to thought leaders (Brad Frost, Dan Mall, Jina Anne, Nathan Curtis)- Recommendation to work in product/UX roles first before systems- Importance of systems thinking - looking at things holistically- Ismael: Value of product management skills and understanding users- Learning HTML/CSS fundamentals, semantic structure, and inheritance- Laura: HTML as accessible starting point for newcomersMentorship and Guidance in Design Systems (08:57)- Greg: "The people who see systems are the ones who make them"- Systems thinking as natural progression for some practitioners- Learning from industry leaders but adapting to your specific context- Disclaimer needed: what works for IBM or Spotify may not work for you- Guy: Ask "why" someone wants to get into design systems first- Understanding the process, not just copying outputs- Risk of burnout from always seeing systems and implications- Danger of over-codifying and creating restrictive structuresUnderstanding Your Motivation for Design Systems (17:52)- Different aspects: code, coordination, fame, specific challenges- Tailoring guidance based on individual motivations and goals- Jeremy Keith quote: Design system doc sites are like social media (only show the good)The Unique Nature of Your Design System (18:21)- Austin: Working at Bass Pro Shops vs. big tech companies- Challenge of resources not fitting organizational context- Greg: "Be happy you don't have their problems"- Looking at intricate systems born from problems you don't have- Blessing of not needing those complex solutions- Focus on the problems that are unique to your usersEmbedding Values in Design Systems (20:12)- Laura: We embed our values in the design systems we create- Risk of copying big tech values that don't align with your mission- Small Technology Foundation example: creating alternatives to big tech- Question: Are you taking on values that don't represent your product?Imposter Syndrome in Design Systems (21:08)- Greg: First time experiencing true imposter syndrome in nearly two decades- Reading industry masters and feeling inadequate- Redwoods community response: appreciate not having their problems- Shift in perspective about own work in the space- Focus on what you can do that's more interesting for your usersIdentifying Gaps in Design System Learning (24:44)- Christine: Communication between teams as huge blind spot- Building systems with one product in mind defeats the purpose- Style guides vs. true systems serving multiple products- Need for people at all skill levels to share their learning- Missing links in the learning chain- Everyone has responsibility to share what they're learningThe Importance of Change Management (26:34)- Yesenia: Change management as biggest success or failure factor- Getting people to change what they're doing- Adapting communication to organizational context- Relationship-driven vs. storytelling-driven organizations- Mismatch in communication styles leads to failure- Book recommendation: Switch by Chip and Dan Heath- Not trained in change management but must do it anywayThe People Side of Design Systems (29:32)- Little focus on people side in survey responses- Austin's revelation: "This is about people" shifted everything- Meet people where they're at instead of holding meetings no one attends- Attend their standups and see how design system can help- Laura: Tooling companies ...
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    55 min
  • Recap: Episode 066 of The Question with Ben Callahan & Laura Kalbag on The Design System Learning Curve

    Recap: Episode 066 of The Question with Ben Callahan & Laura Kalbag on The Design System Learning Curve
    Jan 16 2026

    Episode 66 Recap: The Design System Learning Curve with Ben Callahan and Laura Kalbag

    Ben and Laura unpack the episode 066 deep dive conversation on how people learn design systems, exploring why imposter syndrome is so prevalent in this space, the challenges of being self-taught in a field with no formal education path, and how the community might create better learning resources and pathways for newcomers.

    Topics
    Imposter syndrome and qualification (00:00-06:12)
    - Do people feel qualified as design system specialists?
    - Connection between self-taught learning and lack of confidence
    - Systems thinkers: "The people who see systems are the ones who make them"

    Learning paths and skills development (06:12-09:00)
    - How practitioners learned: scrappy, experimental, self-taught
    - Value of working in other roles first (product design, development, product management)
    - Design systems as increasingly broad field requiring specialization

    Systems thinking benefits and challenges (07:23-09:00)
    - Risk of burnout from always seeing systems
    - Danger of over-codifying and creating restrictive structures
    - Managing your systems brain

    Community learning and resources (16:39-20:52)
    - Challenge of finding good information amid AI-generated content
    - Value of human connection and community curation
    - Potential for gathering trusted resources rather than top-down standards

    Academic vs. practical preparation (16:39-18:28)
    - Gap between art school confidence and professional readiness
    - Sparkbox's apprenticeship program: paid 6-month positions to bridge the gap
    - Creating materials for professional practice, not just theory

    AI's impact on learning and entry positions (18:28-19:54)
    - Difficulty finding trustworthy information
    - Machines talking to machines with no human wisdom
    - Entry-level positions being impacted

    The unique moment we're in (21:46-22:34)
    - Early design system practitioners now in leadership roles
    - Potential for more fertile soil with leaders who understand the work
    - Question: how do we build the pipeline?

    Standardization and community resources (21:04-21:46)
    - Building on existing HTML patterns
    - Brad Frost's global design system concept
    - Component galleries and shared understanding

    Resources
    - Recap of Episode 055 with Lauren LoPrete on Managing your Systems Brain
    - To Be a Leader of Systems by Hazel Weakly
    - Ben on LinkedIn
    - Laura on LinkedIn
    - Get The Question in your Inbox
    - Redwoods Design System Community
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    24 min