iiinova — where your digital self keeps evolving

Ben Callahan @bencallahan.com · 21/09/2026

Round two with @shaunbent.co.uk for Episode 081 of The Question! We're talking how #designsystems adapt to and shape the cultures they serve. Answer before Wednesday 5pm Eastern: bit.ly/answerTheQuestion

Title card for The Question: Design System Deep Dives, Episode 081 — "The Culture We Build," September 24, 2026. Black-and-white headshots of co-host Shaun Bent (left) and host Ben Callahan (right) flank a large slash graphic.

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Ben Callahan @bencallahan.com · 24/08/2026

Welcoming Robin Di Capua and @taylorcashdan.bsky.social as co-hosts for Episode 080 of The Question! We're unveiling The Redwoods Compass, a tool for visualizing #designsystem health, no grades attached. Answer before Wed COB and join the deep dive Friday at Noon Eastern!: bit.ly/answerTheQuestion

Title card for The Question: Design System Deep Dives, Episode 080 — "Visualizing Design System Health," August 28, 2026. Black-and-white headshots of co-hosts Robin Di Capua and Taylor Cashdan sit left of a slash graphic, with host Ben Callahan to its right.

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Ben Callahan @bencallahan.com · 20/07/2026

Episode 078 of The Question is live! Kacey Wood joins me to dig into the psychology of #designsystems work: reactance, pushback, and how you convince people without triggering their defenses. Answer before Wed 5pm ET and join Thursday's deep dive: bit.ly/answerTheQue...

Title card for The Question: Design System Deep Dives, Episode 078 — "The Psychology of Design Systems," July 23, 2026. Black-and-white headshots of co-host Kacey Wood (left) and host Ben Callahan (right) flank a large slash graphic.

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Ben Callahan @bencallahan.com · 06/07/2026

@laurenloprete.bsky.social joins me on Episode 077 of The Question to talk culture vs. compliance in #designsystem work, and when relinquishing control actually pays off. Answer by Wed 5pm ET: bit.ly/answerTheQue...

Episode cover for The Question: Design System Deep Dives, Episode 077 — 'Design System: Culture vs Compliance,' airing July 9, 2026. Hosted by Ben Callahan, with co-host Lauren LoPrete.

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Ben Callahan @bencallahan.com · 15/06/2026

ToniAnn Drenckhahn and I are digging into craft in #designsystems this week on The Question (ep. 076): teach vs. encode, what's actually worked, and where the gap comes from. Answer by Wed 5pm ET to get the invite: bit.ly/answerTheQue... We can't do this without you 💚🌲

Episode cover for The Question: Design System Deep Dives, Episode 076 — 'Enabling Craft through a Design System,' airing June 18, 2026. Hosted by Ben Callahan, with co-host ToniAnn Drenckhahn.

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Ben Callahan @bencallahan.com · 18/05/2026

Cassie Groos is my co-host this week for Episode 075 of The Question! We're talking about the #designsystems identity crisis—how our roles are rapidly shifting in real time. Join us by answering The Question before Wednesday at 5pm Eastern: bit.ly/answerTheQuestion

Episode cover for The Question: Design System Deep Dives, Episode 075 — 'The Design System Identity Crisis,' airing May 21, 2026. Hosted by Ben Callahan, with co-host Cassie Groos.

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Ben Callahan @bencallahan.com · 06/05/2026

Gathering some interesting data for this episode with @kaelig.fr! One of the questions: "As AI agents and automation tools produce more content, design, and code at scale, what are your biggest #designsystem concerns?" Answer today to join us tomorrow at Noon E → bit.ly/answerTheQue...

Bar chart showing survey results for the question 'As AI agents and automation tools produce more content, design, and code at scale, what are your biggest design system concerns?' Results: Inconsistency accumulating faster than we can detect, 63.2% (36); Losing the feedback loops that inform system evolution, 59.6% (34); The system being used incorrectly or out of context, 56.1% (32); New patterns emerging that we can't see, 54.4% (31); Other or N/A, 10.5% (6).

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Ben Callahan @bencallahan.com · 04/05/2026

Welcoming @kaelig.fr as my co-host this week for Episode 074 of The Question! We're talking about how AI is impacting #designsystem visibility and the shifting balance between enforcement and enablement. Join us by answering The Question before Wednesday at 5pm Eastern: bit.ly/answerTheQue...

Episode cover for The Question: Design System Deep Dives, Episode 074 — 'AI and Design System Visibility,' airing May 7, 2026. Hosted by Ben Callahan, with co-host Kaelig Deloumeau-Prigent.

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Ben Callahan @bencallahan.com · 25/03/2026

Hello, system thinkers! Just a few hours to get answers in for The Question, Ep 071 with myself and @vitalyf.bsky.social! Answer today to attend the deep dive tomorrow at Noon Eastern. We're diving into the criticality of #designsystems. But we can't do it without you! bit.ly/answerTheQue...

Episode cover for The Question: Design System Deep Dives, Episode 071 — 'The Criticality of Design Systems,' live on March 26, 2026. Hosted by Ben Callahan, with co-host Vitaly Friedman.

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Ben Callahan @bencallahan.com · 09/02/2026

We're talking "#designsystems as AI Context" this Thursday on Episode 068 of The Question with co-host TJ Pitre! Answer here to join the deep dive → bit.ly/answerTheQue...

Ben Callahan and TJ Pitre will co-host Episode 068 of The Question on February 12, 2026 covering the topic, "Design Systems as AI Context"

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Ben Callahan @bencallahan.com · 26/01/2026

Episode 067 of The Question with co-host Yesenia Perez-Cruz is LIVE and ready for your input! We're talking about #designsystems that differentiate. Answer by Wednesday at Noon E to join the deep dive on Thursday at Noon E! bit.ly/answerTheQue... See you Thursday!!

Ben Callahan and Yesenia-Perez-Cruz will co-host Episode 067 of The Question on Jan 29, 2026 discussing the topic of design systems that differentiate.

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Ben Callahan @bencallahan.com · 14/01/2026

Hi there, system thinkers! Just a few hours left to get your answers in for Ep 066 of The Question (the first one of 2026)! @laurakalbag.bsky.social is joining as co-host to discuss "the #designsystem learning curve" and we need you to make it work! Q3 is a doozy 😵‍💫 bit.ly/answerTheQue...

Question three for this episode reads, "In the world of the web, we have the W3C: “The World Wide Web Consortium develops standards and guidelines to help everyone build and enjoy a web based on the principles of accessibility, internationalization, privacy and security.” Do you believe we need a similar set of industry-wide design system standards?"

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Ben Callahan @bencallahan.com · 17/11/2025

The Question Episode 064 with co host @pegahahmadi.bsky.social is LIVE and ready for your answers! This week, we're discussing #designsystems ethics and we need YOUR voice to make it happen! Everything you need to join in is here → bit.ly/answerTheQue...

Ben Callahan and Pegah Ahmadi will co host Episode 064 of The Question on The Ethics of Design system this Thursday, November 20, 2025 at Noon Eastern.

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Ben Callahan @bencallahan.com · 20/10/2025

The Question Episode 063 is open and ready for your answers! It's about the agreements needed between #designsystems in a system of systems architecture. Should be a nice deep dive into some niche systems thinking! Answer by Wed to get an invite to the deep dive on Thur! bit.ly/answerTheQue...

Ben Callahan and Erin Potter will co host Episode 063 of The Question on the topic of Contracts Between Design Systems this Thursday at Noon Eastern.

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Ben Callahan @bencallahan.com · 09/10/2025

Jumping into an accessibility workshop with Layshi Curbelo at @penpot.app Fest! Great storytelling right out of the gate!

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Ben Callahan @bencallahan.com · 09/10/2025

Watching @gloria.design share some designer ↔️ developer nuggets at @penpot.app fest!

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Ben Callahan @bencallahan.com · 22/09/2025

The Question Episode 061 with this week's co host @natalyathree.bsky.social is LIVE! Answer here bit.ly/answerTheQue... and join us on Thursday at Noon Eastern for the deep dive into how our skills as #designsystems practitioners are evolving. See you Thursday!

Ben Callahan and Natalya Shelburne will co host The Question Episode 061 on the topic of our evolving design system skills.

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Ben Callahan @bencallahan.com · 19/08/2025

Welcome back to The Question, @nathanacurtis.bsky.social! This week, we're exploring where #AI is failing #designsystems. Answer by Wednesday to get your invite to the deep dive on Thursday at Noon Eastern: bit.ly/answerTheQue... This only works if you join in! See you Thursday, b

Ben Callahan and Nathan Curtis will co host The Question, Episode 060 on Where AI is Failing.

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Ben Callahan @bencallahan.com · 05/08/2025

Hello, system thinkers! Episode 059 of The Question with @kevincoyle.bsky.social is LIVE. Get ready, we’ll be doing a #designsystem #AI pulse check. Answer here → bit.ly/answerTheQuestion ← to join the deep dive this Friday 🙌 Thank you to Omlet (bit.ly/4lPO01H) for making this episode possible 💛

Ben Callahan and Kevin Coyle will co host Episode 059 of The Question—a Design System AI pulse check—on August 8, 2025.

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Ben Callahan @bencallahan.com · 21/07/2025

*The Question, Episode 058 is LIVE and ready for your answers* Join Adrianne Daley and I to discuss tracking #designsystem deviation metrics on Thursday at Noon Eastern! All the details here: → bit.ly/answerTheQue...

Ben Callahan and Adrianne Daley will co host episode 058 on July 24, 2025 discussing tracking design system deviation.

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Ben Callahan @bencallahan.com · 07/07/2025

Episode 057 of The Question is live! I'm excited to welcome Ismail Hamila and Steve Dodier-Lazaro as co hosts to facilitate a conversation about #designsystem rigidity vs flexibility and we'd love to have your voice represented! Answer to join the session this Thursday! → bit.ly/answerTheQue...

Ben Callahan, Ismail Hamila, and Steve Dodier-Lazaro will co host a deep dive on July 10, 2025 discussing design system rigidity vs flexibility. This is Episode 057 of The Question.

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Ben Callahan @bencallahan.com · 23/06/2025

Episode 056 of The Question with co host @bradfrost.com is officially open for answers! If you work on #designsystems and you've ever felt overwhelmed by the complexity of your organization, this is the episode for you. Answer today so you can join us this Friday! bit.ly/answerTheQue...

Ben Callahan and Brad Frost will co host Episode 056 of The Question on the topic of "Consistency in Diverse Product Orgs". Deep dive this Friday, June 27, at Noon Eastern.

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Ben Callahan @bencallahan.com · 12/06/2025

About to start the deep dive for Episode 055 of The Question with @laurenloprete.bsky.social ! Totally going to be a great convo. 🙌

Zoomed out screenshot of the Episode 055 FigJam where we capture notes about the topic of the week.

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Ben Callahan @bencallahan.com · 11/06/2025

Last couple hours to get your answers in for The Question Episode 055 where @laurenloprete.bsky.social and I will facilitate a deep dive into the data YOU provide! If you want to join, answer here → bit.ly/answerTheQue... See you Thursday? #designsystems #systemsthinking

Ben Callahan and Lauren LoPrete will co host Episode 055 of The Question covering the topic of managing your systems brain on Thursday June 12 at noon Eastern for 1 hour. Learn more at bencallahan.com/the-question

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Ben Callahan @bencallahan.com · 09/06/2025

Episode 055 of The Question, featuring @laurenloprete.bsky.social as co host, is OPEN for answers! This week, we're asking you about how your "systems brain" impacts your life outside of your job. This only works if you're willing to share your experience. Join us: bit.ly/answerTheQue...

Ben Callahan and Lauren LoPrete will co host Episode 055 of The Question on Thursday June 12, 2025 on the topic of managing your systems brain.

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Ben Callahan @bencallahan.com · 04/06/2025

Here's a snippet from The Question last week with @guysegal.bsky.social. In this clip we're discussing the interesting "Golidlocks" problem of #designsystem flexibility. Next week, @laurenloprete.bsky.social is co hosting to talk "Managing your Systems Brain"—get signed up! bit.ly/3U1hdf3

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Ben Callahan @bencallahan.com · 14/05/2025

Just a few hours left to join the Design System of the Future episode of The Question (happening this Friday at Noon Eastern)! It's free, you just have to tell me your vision for the future of #designsystems → bit.ly/answerTheQue... See you Friday!

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Ben Callahan @bencallahan.com · 12/05/2025

Hello System Thinkers! The Question is open for the week of May 12, 2025. **We're talking #DesignSystems of the Future** Answer by Wed May 14 at Noon Eastern to get your invite to the deep dive on Fri May 16 at Noon Eastern. This one is really going to be fun!

Ben Callahan and ToniAnn Drenckhahn will co host The Question Episode 053 on May 16, 2025 at Noon Eastern on Design Systems of the Future!

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Ben Callahan @bencallahan.com · 07/05/2025

We had such a fun conversation last week on The Question. Major thanks to @yasmine.is and Hakan Bakkalbasi who joined as panelists. And, of course, to the fabulous Rebecca Garza-Bortman (www.rebeccabortman.com), my co host! See the raw data and FigJam files here: bit.ly/44V5Z11

A screenshot from the FigJam for The Question Episode 052 where we asked our panelists about design system adoption.

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Ben Callahan @bencallahan.com · 04/03/2025

Happy Tuesday, system thinkers! This week on The Question, I'm joined by Carlos Báez to talk about the bias in our #designsystems, and how to alleviate it. Answer by Wednesday at Noon Eastern to join the deep dive this Friday! 👉 bit.ly/answerTheQue... See you there?

Ben Callahan and Carlos Baez will co host The Question on March 7, 2025 at Noon Eastern on the topic of design system discipline bias.

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Ben Callahan @bencallahan.com · 24/02/2025

The Question is live for the week—answer by Wednesday to join the deep dive on Thursday! Mina Markham is joining as co host and we're talking about what to do when you have multiple #designsystems. bit.ly/answerTheQue... It's gonna be a fun one!!

Ben Callahan and Mina Markham will co host The Question on Feb 27, 2025 at Noon Eastern.

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Ben Callahan @bencallahan.com · 17/02/2025

Hi, system thinkers! The Question, Episode 046 with Brian Alfaro is ready for your answers! Get them in by Wednesday at noon Eastern to get your invite to the deep dive on Thursday. We'll be talking Vernacular #designsystems! 💥 bit.ly/theQuestion46 💥

Ben Callahan and Brian Alfaro will co host The Question, Episode 46 on Vernacular Design Systems Thursday Feb 20 2025 at noon Eastern!

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Ben Callahan @bencallahan.com · 10/02/2025

Happy Monday, #designsystem friends! The Question is live for the week and @dougneiner.bsky.social will be joining me as co host to talk about how example applications can help a DS team stay close to the work. Answer by Wednesday at Noon to attend the deep dive this Thursday! bit.ly/4hqFbJF

Ben Callahan and Doug Neiner will co host Episode 45 of The Question on Thursday at noon Eastern on the topic of design system example applications. Answer by Wednesday at Noon Eastern to attend!

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Ben Callahan @bencallahan.com · 06/02/2025

I have been waiting over a year to be able to announce this!! I'm so excited and grateful for the #designsystem community for participating. You know who you are! Check out Episode 001 of The Question over on YouTube now! bit.ly/4aKsred

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Ben Callahan @bencallahan.com · 28/01/2025

Gonna be a fun #designsystem consumer panel tomorrow on The Question. If you didn't submit your question in time, just respond to this and ask—I'll DM you a link to register!

Question for tomorrow's design system consumer panel: "What do people say about the design system (or the DS team) when the design system team isn't around?

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Ben Callahan @bencallahan.com · 27/01/2025

This is a fun week for The Question—we have a #designsystem consumer panel happening on Wednesday at noon Eastern! Would love to have you join. Simply submit one question for us to ask the panel, and you'll get an invite: bit.ly/4avdXPg See you there?

Rebecca Garza-Bortman & Ben Callahan will co host a design system consumer panel this Wednesday at noon Eastern.

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Ben Callahan @bencallahan.com · 21/01/2025

We're getting a bit of a late start since folks were off yesterday, but I'm excited to share that @jenniesyip.bsky.social is joining me as co host on The Question this week! You can join too by sharing your experience with a system of systems architecture: bit.ly/4fZ4T6s #designsystem nerds, unite!

Ben Callahan and Jennie S Yip will co host The Question deep dive on System of Systems architecture. Get your invite for Thursday's conversation by answering The Question by Noon Eastern on Wednesday.

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Ben Callahan @bencallahan.com · 13/01/2025

Episode 42 of The Question is LIVE! We're talking designer/developer collab with Spotify DS leader @shaunbent.co.uk—answer The Question by Wed at Noon Eastern to get your invite to the deep dive on Thursday. bit.ly/4gOUBXX #designsystems

Ben Callahan and Shaun Bent will host a design system deep dive on the topic of designer/engineer collaboration on Thrusday, Jan 16, 2025 at Noon Eastern. Answer The Question to get your invite!

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Ben Callahan @bencallahan.com · 07/01/2025

Found a use for the snow here in Ohio!

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Ben Callahan @bencallahan.com · 06/01/2025

I'm very late to the sourdough game, but had a very meditative time over the break playing with a few recipes. Here is the proof (pun, intended).

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Ben Callahan @bencallahan.com · 06/01/2025

@taylorcashdan.bsky.social is joining this week as co host! If you answer The Question, you can throw tomatoes! (j/k, Taylor—we'll be good 😇)

Ben Callahan and Taylor Cashdan will co host a deep dive into design system content marketing on Friday, January 10, 2025 at noon Eastern. Answer The Question to get your invitation.

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Ben Callahan @bencallahan.com · 12/12/2024

Some interesting answers from you all! Of the 97 respondents: - About 50% have evaluated web components in the last six months - Roughly 40% are currently using web components in their design system - Many are in various stages of consideration or partial implementation #designsystems

Survey responses to the question "have you evaluated web components as a technical solution for your design system in the last six months?" Slightly more than 50% have and roughly 30% have not.

Survey responses to the question, "do you use web components in your design system?" Responses indicated that around 40% do and around 50% do not.

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Ben Callahan @bencallahan.com · 05/12/2024

Over 80% of respondents are trying to offer training of some kind to their #designsystem consumers!

over 80% of respondents selected that they have attempted to offer training to their design system consumers

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Ben Callahan @bencallahan.com · 05/12/2024

Some findings from the week. More than 80% of the folks who responded said designers needed training to take full advantage of the #designsystem assets half or more of the time. (Not really statistically significant, just a convo starter for the deep dive tomorrow.)

A majority of the respondents felt that, in order to take full advantage of what their design system offers, the designers using their assets needed some training.

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Ben Callahan @bencallahan.com · 02/12/2024

Hello curious friends! It's Monday, Dec 2 and The Question for this week is LIVE. We're diving into methods for training our consuming designers how to take full advantage of the #designsystem assets we offer them. Answer by Wednesday to join us on Thursday! bit.ly/3ZvJpsN

Ben Callahan and Diane Larsen will co host The Question on December 5, 2024 at Noon Eastern covering the topic of training design system consuming designers.

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Ben Callahan @bencallahan.com · 17/11/2024

I’ve only started playing with this, but you can tell it you want less of certain kinds of ads here (Settings > Accounts Center > Ad preferences)

Go to ‘Settings’ , ‘Account Center’ , ‘Ad preferences’ to adjust you ad settings.

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