I believe every interaction is an opportunity to learn.
My name is Ben Callahan.
These days, I'm spending time hosting a weekly design system show called The Question, nurturing a community of like-minded learners called Redwoods, and writing a book on design systems.
My Values
I believe there is only one team and that we're all on it.
I believe we should quiet our egos enough that we can actually hear each other. And then I believe we should listen.
I believe in humanity—I'm an optimist to my core. It can get me in trouble, but I'd rather go through life believing the best about people, even knowing I'll occasionally be proven wrong.
I believe in the potential impact of every individual.
Most of all, I believe we should work to be a force for good in the world.
Speaking Engagements
Converge, 2024
Presented in Brighton, UK on October 2–4, 2024I offered a 45 minute keynote presentation called, "Wisdom from the Trees" on my learnings from The Question.
Clarity, 2024
Presented online on September 25–26, 2024I presented my learnings from Symmetry 2024 at Clarity, a design system conference.
Symmetry Pittsburgh, 2024
Presented in Pittsburgh, PA on August 16, 2024I organized and facilitated an intimate gathering of design system leaders to pause, identify, and reflect on the challenges we're facing as an industry. With very limited availability and a dramatically unique format, Symmetry helped identify ways we can restore balance to the design system space.
Front-End Design Conference
Presented in St. Petersburg, Florida on April 25—26, 2024I offered a 45 minute keynote presentation on my learnings from The Question community. The material covers a range of design system concepts, connecting traditional systems thinking with the power of language.
User Experience Lisbon
Presented in Lisbon, Portugal on May 23—26, 2023I offered a full day workshop on maturing design systems to 55 people and a keynote presentation on design system culture to over 400 people.
Clarity Conference
Presented in New Orleans, Lousiana on November 9—11, 2022A 45 minute presentation along with a follow up discussion led by Jeremy Keith on design system culture for Clarity, a design system conference.
Amuse UX
Presented in Budapest, Hungary on October 5-7, 2022I led a full-day workshop on maturing design systems along with a 45 minute keynote and Q&A session on the anatomy of a design system.
Smashing Conference
Presented in Freiburg, Germany on October 5–7, 2022A 45 minute keynote presentation with Q&A led by Vitaly Friedman about the anatomy of a design system.
Writings
Bias in Design Systems
April 26, 2025 | bencallahan.comAn examination of the variety of biases that creep into design systems and a few ideas for how to prevent bias.
Design Systems: What to Work On
October 28, 2024 | bencallahan.comA summary of the deep-dive conversation we had as part of Episode 35 of The Question on prioritizing the right work for a design system program
Analysys vs Synthesis
March 5, 2024 | bencallahan.comThe hardest problems in design systems work can be solved with a simple mindset shift—from analysis to synthesis.
Design System Culture
March 23, 2023 | The Sparkbox FoundryAn exploration of the undeniable link between an organization's culture and the approach of its design system. The technical and creative aspects of a design system are important, but they are only two parts of a three-part puzzle.
Consistency vs Flexibility: The Myth of Creative Restraint in Design Systems
June 9, 2022 | The Sparkbox FoundryThough they have numerous benefits, design systems are still sometimes seen as design constraints. Understand how creating a culture of trust can bridge this gap between consistency and flexibility in your design system.
The Anatomy of a Design System
April 13, 2022 | The Sparkbox FoundryA design system can unify different disciplines and lead to improved consistency, efficiency, and much more. Let's define a shared understanding of how systems connect core brand elements with digital interfaces and empower teams to work together effectively.
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The Question is a weekly collaborative design system learning experiment. Answer one question a week alongside your peers in the industry, and receive an invitation to a deep dive discussion on the answers.