The Question

The Question is open for the week of April 14, 2025!

I'll by joined by my co host, Vitaly Friedman, for Episode 051, where we're discussing design system AI guidelines. Answer by Wednesday at Noon Eastern to join the Episode 051 deep dive!

Important note: the deep dive will be on Thursday, April 17, at Noon Eastern.

Answer The Question

Also, subscribe to the YouTube channel to watch past episodes, checkout the previous episodes listing below, join Redwoods DS community, or schedule 15 minutes with me to learn more about design system coaching or strategy sessions.

Deeper design system conversations

The Question is a very simple form of collaborative learning. Smart people like you sign up to participate because you are looking for a community of design system practitioners that aren't satisfied with the status quo.

Here's how it works. On Monday of each week, I'll email you a question or two. You'll have 48 hours to answer, after which time I'll close The Question and start analyzing the responses.

Anyone who responds receives an invite to a 60 minute call on Thursday or Friday at Noon Eastern of that same week. On this call, I'll share a FigJam file with the aggregated results, a few insights I've gathered, and then open the floor for some guided discussion.

We'll have some surprise guests, some deep design system conversations, and some fun along the way. So many very sharp folks are onboard for this journey. I would love for you to be one of them. Sign up below and come along.

Who is this for?

One thing you’ll notice about those of us interested in design systems—we are wildly inquisitive people. And even beyond this, we’re willing to share the things we’re learning. The Question is built on this foundation of curiosity and contribution.

I've also noticed there is a real desire for deeper conversations in our community. My intention is that The Question will give us some incentive to dig in and learn from each other. If this is you, welcome. You are now part of a community of people who have committed to stay in learning mode. Thanks for being here.

How do I participate?

Simply fill out the form above and you’ll be included. There is no obligation to answer each week, but your invitation to join in the conversation is dependent on you responding.

Got a burning question?

Submit a question to be answered by the community. Of course, no guarentees—but I'll add it to the list. Besides, if you're curious about something, there's a good chance others are too!

Submit a Question

Code of Conduct

Harassment in any form will not be tolerated.

The Question is dedicated to providing inclusive, harassment-free, educational experiences for everyone, regardless of gender, gender identity and expression, age, sexual orientation, ability, physical appearance, body size, race, ethnicity, or religion or lack thereof.

We expect speakers, attendees, sponsors, and hosts to fully comply with these ideals at every event. If you are harassed, or if you witness harassment, please contact Ben Callahan immediately. We reserve the right to determine the appropriate response, including but not limited to expelling individuals from events without a refund.

Don’t be nasty or mean—be considerate and respectful.

If you have any questions or concerns, please contact Ben.

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