Chats with Kent C. Dodds

Will's path runs from designing bucket trucks to self-taught software engineering, education products, and database tooling, and that background gives this episode a distinctive lens: software is still a product people use with bodies, habits, emotions, and mental models. The conversation makes product sense concrete through examples like onboarding timing, course complexity, support workflows, and the small confidence signals that separate stable-feeling products from merely functional ones.

You'll hear why watching users work keeps surfacing across this series, how to tell broken experiences from merely unpopular ones, why user feedback usually improves polish more than strategy, and how product engineers can stay valuable in an agent-heavy future by understanding both the user and the constraints of the software medium.

Homework

Use AI agents more for gathering than executing: explore multiple solution paths, adjacent domains, and missing context before you ship.

Give agents richer context like user demographics, constraints, and likely mental models, then use your own judgment to evaluate what comes back.

Slow down long enough to question assumptions before implementation; use AI as a creativity and critique tool, not just a code accelerator.

Resources

Will King - site

Deploy Empathy (Michele Hansen)

The Mom Test (Rob Fitzpatrick)

Interface Craft (Josh Puckett)

Guest: Will King

Company: Crunchy Data

GitHub: @wking-io

𝕏: @wking__

Host: Kent C. Dodds

Website: kentcdodds.com

𝕏: @kentcdodds

GitHub: @kentcdodds

Youtube: Kent C. Dodds

Video

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Aaron builds in public—Laravel roots, education, and now Solo, a terminal multiplexer–style desktop app for organizing agents and dev stacks. This episode is a practical tour of product sense for developers: watching people work, reading support email with empathy, cow paths vs. fences, and why the “right” architecture can still lose if humans go home furious.

You’ll hear how Aaron reasons from problem → solution when users ask for worktrees, when to duplicate UI affordances even when the model is “one,” and how introverts can still do discovery by treating outreach like an optimization mission—plus niche opportunities outside the Cursor clone gold rush.

Homework

When someone asks for a solution (e.g. a feature), slow down and ask what problem they’re really trying to solve—users often lead with implementations.

Practice user empathy: imagine someone stressed, trying to finish work; question “technically correct” UX that blames the user instead of protecting them (confirmations, back-button data loss, etc.).

If talking to people is hard, reframe discovery as a systematic search (spreadsheet energy, trusted partners, or domain friends)—or pair with someone who loves conversations.

Resources

Aaron D. Francis — X

Jobs to Be Done (Clay Christensen)

The Design of Everyday Things (Don Norman)

Guest: Aaron D. Francis

Company: Solo & Laravel education

GitHub: @aarondfrancis

𝕏: @aarondfrancis

Host: Kent C. Dodds

Website: kentcdodds.com

𝕏: @kentcdodds

GitHub: @kentcdodds

Youtube: Kent C. Dodds

Video

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Dillon's path runs from internal insurance tools to Vercel Domains to Cloudflare's agent and dashboard work-always with the same through-line: care about the user, get real feedback, and invest in primitives so delighters don't collapse under bad foundations. This episode covers metrics and paging as a product habit, learning from customer escalations, scoping small when AI speeds up coding, and building cross-functional relationships (support, sales, finance) as part of engineering judgment.

You'll hear practical parallels with episodes on delighters and onboarding tension, plus why reviewing agent-written code still matters for system intuition when things break at 2 a.m.

Homework

Try hard and care a lot; more practically, focus on foundations and primitives.

Put good feedback systems in place so you know what's going on with your product and where it doesn't feel good-alerting and metrics, customer journey signals, or customer interviews.

If you have a customer support team, sit with them and watch them triage cases for your product; get to know support-they're sitting on a gold mine of product signal-and empathize with them like you do with users.

Kent's shorthand for the mindset Dillon agreed with: make pain painful-if your users are hurting, you should feel it too.

Resources

Cloudflare - Developers

Cloudflare Agents

Dillon Mulroy - site

Dillon Mulroy - GitHub

Guest: Dillon Mulroy

Company: Cloudflare

GitHub: @dmmulroy

X: @dillon_mulroy

Host: Kent C. Dodds

Website: kentcdodds.com

X: @kentcdodds

GitHub: @kentcdodds

Youtube: Kent C. Dodds

Video

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Wayne blends delivery and product leadership—his stories range from a flagship-adjacent launch that nobody used to the everyday discipline of listening to customers without waiting two weeks for a meeting. This episode connects feedback-loop thinking (familiar from CI) to product discovery, yes-and conversations when someone is married to a feature idea, and the difference between hygiene features, performance features, and delighters when teams ship faster than users can absorb.

You'll also hear grounded takes on when "move fast" breaks trust, how AI may reshape search-and-listing UIs, and a concrete reading list: The Mom Test and Crossing the Chasm.

Homework

Talk to people, ask good questions, and listen—Wayne says that's the biggest hack that's worked in his career.

Read The Mom Test: ask how people solved this problem in the past instead of whether they like your idea or would use it—you get far more useful insight (Wayne ties this to caring about the problem, not your solution).

Resources

The Mom Test (Rob Fitzpatrick)

Crossing the Chasm (Geoffrey Moore)

Thoughtworks

Wayne Allan — LinkedIn

Guest: Wayne Allan

Company: Thoughtworks

𝕏: @xWayfinder

Host: Kent C. Dodds

Website: kentcdodds.com

𝕏: @kentcdodds

GitHub: @kentcdodds

Youtube: Kent C. Dodds

Video

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Dax has spent years building tools developers actually use; on OpenCode he's thinking hard about product process while the space moves at breakneck speed. This episode is a practical look at product deterioration (not just code rot), bottom-up adoption for dev tools, and how coding agents change who decides what gets built—without replacing the need for taste, restraint, and clarity about what problem you're solving.

You'll hear concrete examples from OpenCode's terminal UI and onboarding, parallels to Kent's Epic Workshop app, and a grounded take on inference pricing, hype, and when "ship messy and fix later" does and doesn't hold up.

Homework

Convince yourself that getting good at product really matters—Dax says there's a lot in the culture that tries to tell you it doesn't, and you need that commitment because the belief will be challenged.

If you don't already believe it, figure out how to make yourself believe it matters (Kent's recap of the guest's action).

Resources

OpenCode

OpenCode docs

Dax Raad (site)

Kent C. Dodds — blog

Guest: Dax Raad

Company: OpenCode

GitHub: @thdxr

X: @thdxr

Host: Kent C. Dodds

Website: kentcdodds.com

X: @kentcdodds

GitHub: @kentcdodds

Youtube: Kent C. Dodds

Video

Watch this episode on YouTube