Ben Callahan
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Ben Callahan
@bencallahan.com
1K followers 300 following 180 posts
Curious guy, systems thinker, Founder of Redwoods, The Question, & Sparkbox, design system consultant and coach. Loves coffee, photography, poetry, volleyball, and cheating at hide and seek.

https://bencallahan.com/

https://sparkbox.com/
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You all are looking beautiful today!!!

@zeroheight.com #converge
October 30, 2025 at 10:06 AM
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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.
October 20, 2025 at 11:48 AM
bencallahan.com
Jumping into an accessibility workshop with Layshi Curbelo at @penpot.app Fest!

Great storytelling right out of the gate!
October 9, 2025 at 12:58 PM
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Watching @gloria.design share some designer ↔️ developer nuggets at @penpot.app fest!
Gloria walking on stage at penpot fest!
October 9, 2025 at 10:02 AM
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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.
September 22, 2025 at 12:06 PM
bencallahan.com
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.
August 19, 2025 at 11:26 AM
bencallahan.com
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.
August 5, 2025 at 9:38 PM
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*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.
July 21, 2025 at 12:31 PM
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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.
July 7, 2025 at 11:46 AM
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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.
June 23, 2025 at 11:40 AM
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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.
June 12, 2025 at 3:47 PM
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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
June 11, 2025 at 12:49 PM
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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.
June 9, 2025 at 12:07 PM
bencallahan.com
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
June 4, 2025 at 3:52 PM
bencallahan.com
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!
Design System of the Future
May 14, 2025 at 1:04 PM
bencallahan.com
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!
May 12, 2025 at 2:10 PM
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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.
May 7, 2025 at 9:37 PM
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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.
March 4, 2025 at 1:06 PM
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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.
February 24, 2025 at 2:09 PM
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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!
February 17, 2025 at 7:45 PM
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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!
February 10, 2025 at 1:46 PM
bencallahan.com
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
February 6, 2025 at 6:35 PM
bencallahan.com
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?
January 28, 2025 at 11:05 PM
bencallahan.com
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.
January 27, 2025 at 1:24 PM
bencallahan.com
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.
January 21, 2025 at 4:45 PM