When Samsung’s CEO asked Federico Casalegno to redesign the cameras on the company’s phones, Federico told him he was the wrong person for the job. He wasn’t an optical engineer. He didn’t understand cameras. What he understood was storytelling — and he pointed to the Lascaux caves in France, where people were marking walls twenty thousand years ago for the same reason we hold up our phones today: to capture a moment, and tell it to someone we love.

That’s the kind of answer you get from a designer who arrived by way of studying human society. Federico is Head of Samsung’s Global Design Studios, with teams spread across San Francisco, Europe, and Seoul. Before that he spent two decades at MIT, where he co-founded the MIT Design Lab with Bill Mitchell, and before that he was a social scientist embedded with engineers and psychologists at Philips Design in the nineties — back when “cross-disciplinary” wasn’t yet a word anyone put on a job posting.

We talk about what that looks like in practice at the scale Samsung operates at. His team builds digital twins of human ears — thousands of 3D and 4D scans across real demographics — then simulates millions of variations to figure out how an earbud should fit. Then they strap the buds onto robots and make them run. Then they test with actual humans, because at some point a person still has to decide what “comfortable” means.

There’s a phrase Federico kept returning to: technology without humanity is merely perfection without purpose. The designer’s role is problem making first, problem solving later.

We also get into how critique works inside a company that speaks a dozen native languages, what he actually looks for when hiring, and the French philosopher who, at 102, looked at his calendar and said he was booked until next year.

Bio

Federico Casalegno is Executive Vice President at Samsung, where he leads product experience innovation across business units and heads the company’s Global Design Studios. Reporting directly to the CEO, he builds teams of designers, engineers, creative technologists, and strategists working on advanced design and next-generation experience planning. As head of design and AI, he established Samsung’s Computational Design function and leads digital transformation across the organization.

Before Samsung, Federico spent two decades at MIT, where he founded the MIT Design Lab and the MIT Mobile Experience Lab and taught at MIT and the MIT Media Lab, researching the intersection of design, AI, and emerging technology. He previously worked at Motorola and Philips Design, and holds a PhD in sociology from the Sorbonne.

Premium Episodes on Design Better

This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. New premium subscriber benefit:

We’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

Premium subscribers get access to the documentary Design Disruptors and our growing library of books. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show.

And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

Read more

Catt Small is a Staff Product Designer at Dropbox, the author of The Staff Designer: Grow, Influence, and Lead as an Individual Contributor (Rosenfeld Media, December 2025), and the host of the Catt’s Corner podcast. She’s sixteen years into a design career that started in Photoshop and Notepad++ — which is why, when she looks at the anxiety rippling through the design community right now, she doesn’t see an unprecedented rupture. She sees a field that briefly forgot how much it used to change.

We spoke with Catt about why this round of tool churn feels more frightening than past ones, especially for designers who came up entirely in Figma. We then talked about career ladders as a negotiation rather than a fixed object, where the optimism in the field is coming from, what her game development background brings to her work, and the origins of both The Staff Designer and the Catt's Corner podcast.

This special edition of The Roundup is brought to you by Shift UX 2026, a new conference from Rosenfeld Media on the future of UX — September 24–25 in New York City and online. Learn more →

UX is having an identity crisis — and that’s exactly why you should be at Shift UX 2026. Join us September 23-25 in NYC or online for a conference built for a moment when “UX” is pivoting from job title to mindset — one hat will ihave impact in ways and settings we’ve not imagined before.

Hosted by Rosenfeld Media, Shift UX brings together designers, researchers, product managers, content designers, and anyone responsible for experiences. We’ll dig into four practice pillars — systems-level thinking, research as strategy, human-centered tooling, and operations as orchestration — through sessions and activities with speakers like Catt Small and Jesse James Garrett. You’ll learn how to keep humans in charge as AI lands in every product and org chart.

Grab your ticket at https://shiftuxconference.com/ and use code DesignBetter75 for $75 off.

Get your ticket

Eli Woolery: You’re delivering the keynote at Shift UX, and your premise is that UX has changed before — and that it’s in a period of pronounced change right now. Give us the highlights.

Catt Small: I’ve been in design — this is year sixteen for me. Initially I was a web designer. That title is still used now, but it means different things at this point. My first tools were Photoshop and Notepad++, if anyone remembers that. Now I work in Figma, and there are lots of other tools coming out of the woodwork.

I’m essentially going to assert that stability has actually been the exception for this field. Within my first decade or so of working in design, there were so many moments where the tooling constantly was changing. We had Axure and a bunch of wireframing tools for a moment. We had Sketch, which some people still of course use, and Figma. And we also had a period of prototyping in code back in 2013, 2014, 2015. I remember the should designers code conversation, if y’all remember that.

So for me, the norm is actually change. I’m seeing a lot of people saying we’re cooked and everything is going away. And I actually want to assert that we got really comfortable — and that’s not a bad thing or a good thing. It’s just that we had a moment where people all agreed what it looked like to create digital products, and now we’re realizing there might be other ways to do it. That’s really scary, but it also comes with a lot of opportunity. You might actually have the chance to design what your job looks like more, and to have the career ladder become more of a conversation.

Aarron Walter: In past shifts I mostly saw excitement — designers like new tools and new trends. This time what I see is anxiety: I’m not going to be able to keep up, and I feel very vulnerable at work. What have you noticed about designers’ outlook?

Catt: I’ve seen a lot of designers get used to being told what the expectation is rather than bringing their own opinion. And part of that most likely relates to the fact that for a moment we had all agreed what it meant to design, what the product development lifecycle looked like. We had the double diamond and we had the tooling.

Now we have AI, we have all these different options. We have the canvas, or do you just prototype? Should designers code 2.0 is here. Some people are senior designers and they’ve been working for six years, and six years ago was a point where everybody was using Figma. So this moment is very terrifying for those people who literally came up only using Figma.

You have a lot of people who are just terrified, and they’re very used to their companies having to define the career ladder and explain what it means to be a good designer. Now we all have to tell companies what that is. So in some ways we’re back to the conversations about the ROI of design, or design advocacy, and all the design maturity conversations. Time is a bit of a circle. Things are different this time, but I feel shades of prior conversations.

For those of us who have been around for a while, it’s like, okay, got it. We have to be scrappy and ready to experiment and view this as a series of scientific explorations, and that’s how I’m treating it.

But there is the reality, which is these are jobs. People are nervous that this change means they won’t have a job moving forward. Or maybe they might be mourning the version of the job they thought they were going to have. And that’s also very real, and I want to acknowledge that. But if you want to keep doing design work in the near to long-term future, adaptability is a required skill, and everybody is going to be building it right now.

Eli: A lot of people think of a career ladder as a fixed object you climb, hand over hand. You’ve stayed largely on the IC track — it sounds like you see it as more flexible than that.

Catt: Jobs have always been a conversation. Of course there are times where leadership notices there’s a gap and the job is very clearly defined. And then there are moments where people aren’t really sure and they look to you — especially if you have some experience — to tell them what they need, because you’re closer to the work.

This is a shift I’ve had to nudge a lot of designers for, especially designers who go up the ranks from senior to staff. There’s this expectation when you’re a senior or a mid-level or a junior designer that the job is defined for you, you are told what to do, you do that. There’s a lot of security and safety in that. But there’s usually a maximum level that you’ll get to when you operate that way.

When you start to actually tell leadership what you think needs to happen, and you do that in a way that helps them make informed decisions, then that is leadership. It’s just a different kind of leadership than what you’re used to.

Senior leaders know a lot of things. That said, they don’t know everything. So it is on us to highlight what potential opportunities there might be that they’re missing. You can have that conversation, or you can not and let that drop. That is an explicit choice.

And literally this moment we are in right now — you can either be apathetic and say, I don’t know, I’m just going to get fired. Or you can say, okay, how does this change how I work, and how can I ultimately create better outcomes for people by using these tools? I’ve helped build career ladders at most of the companies I’ve worked at, at least in the latter half of my career. So I’m very used to this idea that I’m not being told what to do. I’m helping other people make informed decisions.

Aarron: It’s not all pessimism. What do you see from the designers who are genuinely excited about their new skills and the blurry lines between roles?

Catt: People feel a bit of the magic again. They can actually create some of the ideas that maybe they just didn’t have the skill set to properly illustrate before, and they can actually build them, and they can actually push them live.

On my podcast I spoke with Edwin Morris, a staff product designer over at Jane Street, who encapsulated this really well. He said that he’s just in it because websites are really cool. We’re seeing a lot of people remember, why did I get into this in the first place? It’s because sometimes this stuff can be magical. It’s so cool to type words on a screen. It used to be just literally in code. Now you can type words into a conversation window and then something moves. I want people to continue to feel that magic.

Eli: You’ve also been involved in game design. What parts of that do you bring to your day-to-day work?

Catt: I do think a lot about movement and animation, because of my game development background. Historically you had to be pretty good at motion design and at using very particular tools that are not always the easiest to wrap your brain around. Not to say that I didn’t try —

Eli: Everybody loves After Effects though, right?

Catt: After Effects is tough. Shoutout to Adobe. So I love that the tooling has simplified in some aspects. It’s more accessible to people.

And it’s cool that now it’s easier to make certain animations happen. I literally, for a certain project, wanted to have this form — on submission, rip off the piece of paper, quote unquote, and then drop into a filing cabinet, and then have the filing cabinet open and close. And that’s Catt’s game development brain there for sure — kitschy UI. I still like that kind of stuff, the cringe UI. But being silly, whimsical — I think we’re going to see more of that. We’re going to see more polish, more animation, more fun. And for me, I bring that spirit for sure from games.

Aarron: Your book, The Staff Designer, looks at the landscape of being an individual contributor and still having influence, without being trapped in a management role. Why did you write it?

Catt: I was struggling to figure out what the expectations were when I was trying to transition from senior to staff. And then I was initially struggling — or really almost drowning, overwhelmed — my first year into the actual position once I got it. And so at that point I was wishing there was a guide, and there was nothing specifically on working at that level as an IC. It was really the gift that I wish I had.

There’s a lot of content out there for managers, and that is historically what we equate with the concept of leadership — leadership equals managing people. But what we are seeing is that some people just like being in the work. And I am one of those people.

Eli: And then you made a podcast.

Catt: The book launched in December of 2025, and that was very early AI shift conversation. We were doing a lot of vibe coding, but we weren’t really being pushed at work to burn tokens, essentially. Now we’re all being required to burn tokens — many companies are requiring people to be in AI all the time, and they’re being measured by that. So I wanted to reopen some conversations with people I had spoken to, to understand how design work is shifting for them.

It coincided with me wanting to do some research for a presentation I gave to folks at Config. I just had personal opinions, and I was like, I can’t go on a stage in front of thousands of people without having done some research. Again — scientist hat. So I decided to talk to eight people, staff and above, plus a design coach who works with staff designers and design managers. And I just really asked them: how are y’all working these days?

It felt like there was a lot of hype, but I wasn’t seeing very much in my own output in terms of quality to the level that I would like. So I was like, let me go talk to other people. And then if there’s something here that helps me feel less crazy, maybe other people will feel less crazy. And the result is the Catt’s Corner podcast.

Aarron: Where can people learn more about you and all the work that you’re doing?

Catt: I have a website — it’s cattsmall.com. And sometimes I post on LinkedIn, but that’s pretty much it. I’m not the most online. I’m also on Bluesky, and my handle there is catt.design.

Catt delivers her keynote, “Your Future is Nebulous—and Why That’s Good,” at 10:15 AM ET on Thursday, September 24 at Shift UX 2026 — in New York City and online, September 24–25.

Grab your ticket at https://shiftuxconference.com/ and use code DesignBetter75 for $75 off.

And we want to hear from you: are you mourning the job you thought you’d have, or designing the one you want? Reply and let us know.

Find Catt at cattsmall.com, on Bluesky at @catt.design, and on LinkedIn at @cattsmall.

Weekly Portfolio Club calls this summer helped our paid subscribers build portfolios that land great jobs. Experts joined us weekly to provide feedback, and we compiled lessons from each session into a portfolio design guide.

Our key takeaway from the experience? Designers need more peer-to-peer support with their work, their careers, and the challenges they face on the job. And regular interaction with senior design leaders helps everyone learn faster.

Design Club: Bi-weekly Zoom design and and career discussions

If you're struggling with the craft of design, need career guidance, want help with tough issues at your job, or want help getting your bearings with AI and the creative process, Design Club is the place to bring your burning questions for peer-to-peer discussions and help from industry experts.

Here’s how Design Club works:

1. Become a paid Design Better subscriber (just $57.60/year) to receive an invitation to our Slack community of designers.

2. Join the #designclub Slack channel and subscribe the Google Calendar with call details.

3. Join us on Zoom every other week to get feedback on a design, talk through work challenges, or lurk and learn from others.

4. We’l bring design experts and leaders into the mix to give you real-world perspectives on your work.

We’ll record all sessions so you can learn from them even if you can’t attend.

Save 20% on annual membership

Your subscription includes a LOT more …

Become an annual member now for just $57.60 and you also get:

✔ Slack design community (talented designers and former guests)
✔ Custom reading and listening recommendations based on your interests
✔ 4 ad-free episodes per month (free subscribers get 2)
✔ The Roundup — weekly insights synthesized from 250+ interviews
✔ The Brief — monthly design deep dive with practical design guidance
✔ Full ebook library — 9 ebooks on design systems, product design, and more
✔ The Toolkit ($1,000+ value)

Save 20% on annual membership

Jonathan Adler was one of our favorite guests, so we’ve been angling to get him back ever since. He started as a potter and now designs furnishings and interiors that are decadent, but layered with meaning and humor. A lot has happened since we last spoke: he had a retrospective at the Museum of Arts and Design — the same institution whose gift shop took a chance on his pots 32 years ago — and launched a sprawling collaboration with Michaels, which he calls a temple of craft.

We talk with Jonathan about what it felt like to stop making long enough to curate three decades of his own work, why he’s grateful he chose commerce over the gallery world, and whether people really are trading doomscrolling for making things with their hands.

Along the way, we talk about his father, the lawyer who painted — and why the maximalist you think you know insists he’s a minimalist. Also, much like our last conversation with Jonathan, there are some instances of adult language and humor, so if you have kids around it might be a good idea to throw on some headphones.

Bio

Potter, designer, and author Jonathan Adler launched his namesake brand after leaving his day job to pursue his first love: pottery. In 1993, Barneys bought his collection of pots, and five years later, he opened his first store in Soho.

Today, Jonathan Adler is a design company with retail locations worldwide, a thriving e-commerce site, a full slate of residential and commercial projects, and a global wholesale business. They strive to create luxe and livable interiors that are seriously designed, but don’t take themselves too seriously. Earlier this year, the Museum of Arts and Design mounted a retrospective of his work, presented in dialogue with pieces he curated from the museum’s own collection. He lives in New York with his husband, the writer Simon Doonan.

Books & links mentioned

Jonathan Adler

• JonathanAdler.com

• @jonathanadler on Instagram

• @jonathanadler on TikTok

Mentioned in this episode

• MAD MAD World: Jonathan Adler — Museum of Arts and Design retrospective Jonathan Adler x Michaels Brass frog bowl

• The Camp 100: Glorious Flamboyance, from Louis XIV to Lil Nas X, by Simon Doonan

• Notes on “Camp” by Susan Sontag Making It by Norman Podhoretz

Jonathan’s books

• My Prescription for Anti-Depressive Living (2005)

• Jonathan Adler on Happy Chic Colors (2010)

• Jonathan Adler on Happy Chic Accessorizing (2010)

• 100 Ways to Happy Chic Your Life (2012)

Elsewhere

• The Retail Pilot: From Pottery to Global Design — The Creative Journey of Jonathan Adler

• How Long Gone, Episode 666: Jonathan Adler

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

Read more

It’s easy to feel like a victim of workplace dysfunctionality. But nobody likes a victim. Even CEOs don’t have complete agency over the workplace. Companies operate on social contracts that may be guided by executives, but every employee plays a part in shaping the environment.

Clay Parker Jones has been studying organizations like an anthropologist for years and has distilled his observations and principles in a new book called Hidden Patterns: A Playbook for More Human Workplaces. He’s been at it close to two decades, first at the digital strategy firm Undercurrent and now as an organizational designer working on it full time.

The book is 75 patterns, and what we like about that structure is that you can pull one without permission from anyone. Clay calls the practice pattern thinking and doing, which “acknowledges that meaningful change can and does begin anywhere, at any level. It doesn’t require formal authority or a big budget.”

We covered a lot of ground with him. Five ideas stayed with us, and here’s how we think they apply to the work designers and tech pros are doing right now.

Design leadership is tough. Get answers, connect with skilled leaders at Creative Leadership Retreat Sept 28-29.

Learn more

Listen to the episode

Clay Parker Jones: Spotify, Apple Podcasts, Substack, Youtube

Already a paid subscriber? Follow this link to set up you premium feeds on Apple, Spotify or any other platform from your phone or computer.

1. Most of us aren't on a team. We're in a group that meets.

Clay’s diagnosis of the modern workplace is short: there aren’t enough real teams. What we have instead are co-acting groups. We gather for a meeting, then scatter back to the work we each do alone.

Think about the people in your last meeting, and ask whether any of you kept working on the same thing after it ended. For a lot of us the answer is no, and we’ve been calling that a team anyway.

When we asked Clay what a good one actually looks like, he didn’t describe a structure. He described a set of relationships.

“Most people that I speak to who have had a great experience at work had it in the context of a team. People that they know, people that they care about, people that care about them.”

—Clay Parker Jones

That’s why so many designers have a distorted sense of how rare this is. Design teams tend to clear the bar without trying, so we assume everyone else works the way we do. They’re mostly not. Greg Hoffman told us something similar in Creativity is a team sport: the good work comes out of the connection between people.

If a group you’re in has no reason to exist between meetings, you can give it one. A decision it owns. A number it watches. Something that you’re working towards together (ahem, better than another OKR). And if you can’t, that’s worth knowing too, because you’ve been holding yourself to a standard the structure was never going to meet.

Read more

We all know that there is something fractured about the workplace, that makes it inefficient, and at times inhumane. If only someone was thinking deeply about those problems, and how to address them…

That’s what Clay Parker Jones is working on right now. Clay has spent close to two decades on this problem — first at the consultancy undercurrent, and today as Head of Org Design and Development at Airbnb. He advocates for investment in creativity and humanity at work, something you might think would be obvious for any company, but sadly is eclipsed by short term thinking.

His new book, Hidden Patterns: A Playbook for More Human Workplaces, is one of the most cohesive philosophies of organizational structure we’ve come across. And his diagnosis of what’s broken is simple: there aren’t enough real teams. Most of us work in what he calls “co-acting groups” — people who convene for a meeting and then scatter back to their actual work.

In this conversation, we get into why psychological safety stays a platitude until you make it structural, what rule of law looks like inside a company, and how to break a manager’s job into atomic pieces and hand away the parts you’re bad at. We also chat about why the org chart is a design problem that designers should be at the table for.

Bio

Clay Parker Jones leads Organizational Design & Development at Airbnb, refining how a creativity-first company learns and ships new ideas. A former Chief Strategy Officer at Black Glass, co-founder of August, and transformation lead at R/GA, his work has been recognized by B Lab and profiled in a Harvard Business School case study. A former bike mechanic with a BA in Diplomacy and World Affairs from Occidental College, Clay now resides in Brooklyn with his wife Emily and cat Ian. You can find him on the Fort Greene tennis courts in his spare time.

Premium Episodes on Design Better

This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

Premium subscribers get access to the documentary Design Disruptors and our growing library of books. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show.

And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

Read more

Yesterday I went to a design leaders happy hour in SF, hosted by Kai Hailey (who led the Sprint Leadership Academy at Google when I first met her in 2018), and Peter Merholz (co-author of Org Design for Design Orgs).

It was fun to see them, and catch up with a few other folks I know from the design & tech world. One of those people happened to be Nick Foster, former head of design for Google X, who we coincidentally had on the podcast almost exactly a year ago.

Recently Nick had been doing some consulting with companies like Anthropic, and it got me thinking, when the present is changing so quickly, how do you even go about designing for the future?

Creative Leadership Retreat 2026 · Sonoma, Sept 28–29
Become a better creative leader in two days: connect with peers in roles like yours, and take fresh methods from eight leaders in film, politics, art and software who lead inspiring creative teams. You’ll leave with people you can call and approaches you can use Monday.

We’re close to sold out, but we have a new 20% discount for Design Better premium members which you can find at the bottom of this post. Discounts end this week.

We also have a limited number of scholarship spots that we are giving out. Learn more and apply here:

Apply for scholarship

None of us know where this is going

The first step in designing for the future is admitting that none of us know where this is all headed. But as designers, it’s a space we can shape, and those who do it best have made peace with not knowing what they’ll find there.

Most of us, as Nick Foster said in his episode, are “comfortable in the world of known problems.” We talk to users, gather insights, iterate on feedback. That loop works when the problem is visible. But what do you do when you’re designing for people who haven’t been born yet, or for technology that won’t arrive for a decade? What do you do when the problem itself is still forming?

That question ran through several of our most provocative conversations this year. One trait kept surfacing in the designers doing the best future-facing work: they’ve learned to be genuinely comfortable not knowing.

Comfort with ambiguity

Nick spent years at Google X on more than 200 moonshots, from flying machines to nuclear fusion. His book, Could, Should, Might, Don’t, argues that most futures thinking collapses into comfortable, predictable patterns that shrink our imagination. He’s blunt about what it takes to resist that:

Read more

A few years ago, Dropbox redesigned its website and revenue dropped by thirty percent. It was an all-hands-on-deck moment: people working weekends, everyone hunting for a systemic failure.

The culprit turned out to be a pricing page — specifically, the white space between the feature list items was slightly too generous. Angel Steger noticed that her eye kept landing on the white instead of the words. They tightened the gaps, and the revenue came back.

That’s the kind of thing Angel notices, and it’s not an accident. Currently the VP of Design at Wealthfront, She trained as an architect at RISD, where the first question in her first architecture class wasn’t about buildings. It was “What is a drawing?” — the sort of question that makes you realize every tool you reach for carries a point of view you probably haven’t examined.

Angel’s path into tech was less deliberate. By her own account, she mouthed off to her boss, got fired, and spent the severance on O’Reilly books, taught herself to code, and became the first designer at MySpace — where the head of engineering proudly informed her that they had never had design and never would need it. She went on to become the first product designer at 23andMe, learned usability from Larry Tesler, and led design teams at Pinterest, Dropbox, and Meta before landing at Wealthfront.

In this conversation, we get into what architecture teaches you about solving one problem at a time, why she tells her team to go lower fidelity, how a default chart setting can push someone into a financial decision they’ll regret, and what she looks for in a portfolio — high craft, high intentionality, and no boiled broccoli.

Bio

Angel joined Wealthfront in November 2023 and leads product design, content design, and creative teams, bringing 20+ years of experience building and leading customer-centric, business-focused design and product teams. What makes her perspective rare is the through-line she draws between business model and design quality — she's a practitioner who built her career arguing that growth design, done with rigor and craft, isn't a compromise but the highest form of product work. Beyond Wealthfront, she holds advisory positions at AudiencePlus and Ameelio, and previously held leadership design roles at Meta, Dropbox, and Pinterest, where major growth and user engagement initiatives were implemented. She guided Wealthfront's design organization through its December 2025 IPO, in which Wealthfront's shares began trading on the Nasdaq Global Select Market under the ticker "WLTH" — the first robo-advisor to go public.

Show notes and links

Do > Show > Tell —

LinkedIn — https://www.linkedin.com/in/angelsteger/
Reforge — https://www.reforge.com/experts/angel-steger
Medium — https://medium.com/@angelsteger
Pixelated Path: "From Architecture to UX Design Leadership" —

Pixelated Path

From Architecture to UX Design: A Conversation with Angel Steger

What can architecture teach you about digital design? More than you might think…

Listen now

2 years ago · 2 likes · Chris Abad and Angel Steger

Some additional thoughts from Angel below:

1. Re: architecture. The third thing is the trial-by-fire nature of architecture school. You don’t get taught anything—you are merely handed problems, and are forced to come up with your own tools to solve them. That was incredible training for tackling very high level problems that a lot of people get scared or overwhelmed about. You get very good at breaking down complexity into something that can get executed.

Architecture is a team sport. You can't build a building alone — mostly you're building the dream of a building, together. That's why we ask, "what is a drawing?" It's a story, a point of view, built to become a shared vision. I struggled with individual work, but in groups I could pull good ideas out of the room and synthesize them into something people rallied behind. I'd end up leading without meaning to. My comfort was in the collective, never in coming down the mountain with two tablets.

2. Interviewing. Why the counter-intuitive portfolio (show what you’re proud of, not just “what’s relevant”) worked for me at Wealthfront: it showed that I’m the kind of design hire that thrives by coloring outside the lines—and made it very clear that hiring me is to hire someone who doesn’t just sit at the table, but actively builds tables, and invites others to build with me. If the hiring team wasn’t on board for that, we both got great signal right away that this wouldn’t work. There is nothing that chips away more at your wellbeing than to be forced into a role that runs counter to your values, your nature, and your strengths—and nothing better than to be set up to be your fully activated professional self.

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

Read more

What Portfolio Club taught us about designing a great portfolio

Of everything you’ll ever design, your portfolio is the hardest to see clearly: you’re too close to judge it the way a stranger would. It’s also easy to spend your energy on styling and lose sight of whether the work itself is presented well. And before styling even matters, there’s the technical work of building the site, which stalls plenty of good portfolios in a Figma file. Claude Code and tools like it can clear that path without taking over your creative decisions, and we’ll walk through how later in this guide.

This guide draws on Design Better’s Portfolio Club critiques, where designers who’ve hired at Apple, Google, Adobe, and beyond review real portfolios on camera. Matt D. Smith, Bob Baxley, Daniel Burka, Brooke Hopper, Jared Erondu, Dan Harden, and Joey Primiani have each spent an hour with us, and their perspective runs through everything below, so you see your own work the way a hiring manager will.

Your portfolio may be the most valuable tool in your career, which matters now, with designers anxious about what AI is doing to the job market. The best answer to that anxiety is action, not reassurance. Build the portfolio. Find the job you want. Stop worrying about the changing world. Start designing for it.

Creative Leadership Retreat 2026 · Sonoma, Sept 28–29
Become a better creative leader in two days: connect with peers in roles like yours, and take fresh methods from eight leaders in film, politics, art and software who lead inspiring creative teams. You'll leave with people you can call and approaches you can use Monday.

Learn More

Portfolio design principles

Read more

Like a lot of parents, Eli struggled over the years to get his kids more into reading and away from screens. He wasn’t necessarily on the search for a technological solution, but then an interesting device came our way: the Yoto Player, a screen-free audio player for kids. Eli’s 10-year old son has been loving to read along to the Harry Potter books (and he often finds him after he falls asleep, and the player is still going).

The story behind Yoto is from a similar moment of parental struggle. About a decade ago, Ben Drury was shopping for a stroller in a London department store and found one with an iPad mount built in. For a newborn. He remembers the reaction being physical — this is just wrong.

But if you’re expecting an anti-screen crusade, that’s not quite what happened . The line Ben uses is: we don’t say screens are bad, we say audio is good. Listening is good for creativity and imagination — and there’s research going back to the 1980s to back that up.

Ben is the co-founder and CEO of Yoto, makers of a kids’ audio player that works by dropping a physical card into a small speaker. Before Yoto Ben spent about a decade building a B2B digital music platform called 7digital which he took public. What he learned from that experience proved helpful as he and his co-founder started Yoto.

Ben and his co-founder became parents at roughly the same time, and wanted a way for their kids to connect with music and books like they did in childhood. So they started hacking on Raspberry Pis with no hardware experience whatsoever. How hard could it be, right?

Turns out, it’s pretty hard. They took a restrained approach. Yoto is a cube, because it was the simplest shape they could think of. It uses NFC cards that have a Pokemon card feel. The 16 by 16 pixel display presents pixel art that gives Yoto a fun personality.

In this conversation, we get into the design principles that came out of Montessori, their experience working with Pentagram on product design and branding, why Paul McCartney became an early angel investor, and what changes when you go from a Kickstarter that raised fifty thousand dollars to nine-figure revenue.

Bio

Ben Drury is the co-founder and CEO of Yoto, the screen-free audio player that lets children control their own listening by dropping a physical card into a speaker. Before Yoto, he spent roughly a decade building 7digital, a B2B digital music platform he took public. He and his co-founder started Yoto in 2017 with a Kickstarter campaign and no hardware experience between them; today the company employs about 220 people across six countries, sells in 1,900 Target stores in the US, and counts Paul McCartney among its early angel investors. He lives in London with his wife and two sons.

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

Read more

The designer Stefan Sagmeister isn’t known for being subtle. A poster he created in 1999, for an AIGA lecture he delivered in Detroit, was carved with an X-acto blade into his chest and torso. One prominent feature was a consistent motto of his, Style = FART.

He later created a whoopee-cushion with the same slogan.

So Sagmeister might appreciate our conversation with Jeff Hammoud, Chief Design Officer at Rivian, who takes a similar stance on design vs. styling.

As designers, we often put a lot of ourselves into our work. Then that work, whether its a concept, a prototype, or a beautiful comp, gets flattened on its way to the real world. Maybe your work wasn’t a car design. Maybe it was an app, a rebrand, a prototype that never survived the handoff to engineering. It comes out the other side and you barely recognize it.

Our conversation with Jeff — recorded live in Miami during Art Basel, in the Rivian Pavilion — was in many ways about how to keep that from happening. Jeff runs a design org of around 140 people spanning interior, exterior, color and materials, digital, and a dedicated studio engineering team. And the red thread running through what he told us was a provocative idea about what design even is.

Listen to the episode

Jeff Hammoud, Rivian CDO: Spotify, Apple Podcasts, Substack, Youtube

Already a paid subscriber? Follow this link to set up you premium feeds on Apple, Spotify or any other platform from your phone or computer.

Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain.

We’re working on putting together some scholarships for this event. Please fill out the short form below if you’re interested:

Scholarship application form →

A code for $15% off (also offsite accommodation) is available for Design Better premium members. Link and code after the paywall below at the bottom of this post.

Constraints are the job

Jeff’s never been drawn to concept cars. To him they’re “gratuitous” — beautiful ephemera that typically never make it to manufacturing. His definition of a designer hangs on the presence of constraints:

“Can somebody design something without any constraints? Yes. And I think working within constraints is really what makes us good designers. Otherwise, we’re just stylists. Can you make a car look pretty? Yes. But can you make it aerodynamic? Can you make it meet the engineering requirements for safety? Can you make sure all the design provides good fit and finish? It’s manufacturable. How do you reduce costs in it without it looking cheap? Those are all the things that are really important as we’re looking to design a vehicle.” — Jeff Hammoud

That’s the “one rule” underneath Rivian’s process: the design team never shows something it doesn’t intend to actually build. And the way they protect that intent is structural. A dedicated studio engineering team sits inside the design org, adjacent to the designers, giving early feedback on manufacturability so the debate over what’s buildable happens before it ever becomes a fight:

“We’ll never show something if we don’t have an intent to really make sure that, if we’re saying we’re going to build this, it looks just like what we show.”

Most of us have lived the opposite. You’ve seen the stunning concept, then the production version that makes you ask, “what happened?” Jeff’s answer is that the gap between concept and reality is where design actually happens, if you’re set up to do it.

The cautionary tale

If you want to see Jeff’s philosophy proven in the negative, look at a story Tony Fadell told us about General Magic — the legendary early-’90s startup where the team that had built the Macintosh set out to build what was essentially the iPhone, but fifteen years too early.

Read more

This is a special bonus episode, an interview with Rivian’s Chief Design Officer, Jeff Hammoud. We’ve got all the audio here, but it’s worth heading over to our Youtube channel at dbtr.co/youtube to watch the video.

We recorded this one live in Miami, in the Rivian Pavilion during Art Basel, with a R1T truck in a new eggplant-purple called Boreal parked just over Jeff’s shoulder.

Jeff runs a team of about 140 people across Irvine and Palo Alto — interior and exterior designers, color and materials, digital surfacing, perceived quality, even an in-house painter and a clay milling shop. And he has a strong opinion about what all that machinery is for: constraints are what separate designers from stylists. Anyone can make a beautiful concept car, but making the production version look like the concept is the challenge.

We talked about why Rivian keeps making colors most people won’t buy, and how limited-run “Studio Originals” work like sneaker drops. Jeff makes the case that AI is going to level the playing field in design — shifting the advantage from whoever illustrates best to whoever has the better idea. We got into which controls stay physical and why, the haptic halo wheels coming in R2, and how scent ties a car to memory.

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

Read more

A field guide to AI prompting

This week, we’re sharing a chapter from Think. Prompt. Create, a book written by Joey Primiani’s, a member of the Design Better community.

Most of the anxiety we hear about AI isn’t really about AI. It’s about not knowing where to start. People tell us they’re worried about their jobs, but when we ask what they’ve actually tried, the answer is usually “not much yet.” The fastest way out of that spiral is the least comfortable one: open the tool and use it badly a few times until you get better at it.

Joey Primiani has put in thousands of hours doing exactly that. He’s a longtime Design Better subscriber, and he just published Think. Prompt. Create: A New Way to Build Software — a book about how to actually work with tools like Claude Code, not just poke at them. It’s a solid on-ramp if you’ve never touched one of these tools, and specific enough that people who already have will still walk away with something. We asked if we could run a chapter. He said yes.

What follows is Chapter 4, “The Art of the Prompt: Talking to Your AI Partner.” It offers a clear breakdown of why some prompts get you exactly what you wanted and others get you three hours of cleanup.

Get Think. Prompt. Create on Amazon →

Chapter 4: The Art of the Prompt, Talking to Your AI Partner

by Joey Primiani

Here is a secret that most Claude Code tutorials bury: the quality of your output is almost entirely determined by the quality of your input. Claude Code is extraordinary, but it is not psychic. It can only work with what you give it. Every frustrating session, every confusing output, every “why did it do that?” moment can almost always be traced back to an ambiguous or incomplete prompt.

The good news: prompt writing is a learnable skill, and the principles are simpler than you might think.

The Five Pillars of a Good Prompt

After thousands of hours working with Claude Code, I have distilled effective prompting into five principles. Master these and you will consistently get better output than most developers.

1. Be Specific About Outcomes, Not Steps

The single biggest beginner mistake is trying to be too prescriptive. People write prompts like:

“Create a function called getUserData, make it async, use the axios library to call https://api.example.com/users/{id}, and return the user object.”

When what they should write is:

“Add a function that fetches a user by ID from our API (https://api.example.com/users/{id}) and returns the user data. We’re already using axios elsewhere in the code.”

The first prompt is a recipe. The second is a goal. Claude Code is a senior developer, give it goals, not recipes. It will make better implementation decisions than you will if you try to micromanage every detail.

The exception: when you have specific, non-negotiable technical requirements, spell them out. “Use async/await rather than promises” or “the function must handle the case where the user doesn’t exist by returning null, not throwing” are legitimate constraints, not micromanagement.

2. Provide Context, Liberally

Claude Code knows your code only as well as it has read it. For a fresh session, that means Claude Code knows only what is in the files in your current directory. For a continuing session, it knows what it has read during the session.

When your request depends on something Claude Code may not have seen, tell it explicitly:

“In our app, authentication is handled by the AuthService class in src/services/auth.js. Given that setup, add an endpoint to /api/profile that returns the current user’s profile data, requiring authentication.”

You just told Claude Code: go read that file, understand how auth works, then implement the endpoint in a way that is consistent.

You can also directly ask Claude Code to read files before proceeding:

“Read src/database/schema.sql and src/models/user.js, then help me add a ‘last_login’ field to the users table.”

Claude Code will read both files and use them to inform its answer.

3. State Constraints Upfront

Every project has constraints, technology choices, coding conventions, performance requirements, compatibility needs. Front-load these in your prompt rather than waiting for Claude Code to make the wrong assumption:

“We’re using vanilla JavaScript with no frameworks. Our database is SQLite through the better-sqlite3 library (not async, it’s synchronous). Add a function to insert a new order.”

Without that context, Claude Code might produce async SQLite code, or use a different library, or assume you are in a React project. With it, you will get exactly what fits your stack.

This is also why the CLAUDE.md file is so valuable, it provides standing constraints for every session without you having to repeat them.

4. Use Examples When the Format Matters

If you have a specific output format in mind, a particular data structure, a specific visual style, a certain code pattern, provide an example:

“I want to add error handling to this function. We handle errors like this elsewhere in the codebase: try { const result = await doSomething(); return { success: true, data: result }; } catch (error) { logger.error('doSomething failed', { error: error.message }); return { success: false, error: error.message }; } Please use the same pattern.”

Examples are unambiguous in a way that descriptions rarely are. Show, do not just tell.

5. Ask for Explanation When You Need to Understand

This is underused. Claude Code is not just a code generator, it is a teacher. If you want to understand what it is doing:

“Add the search functionality, and after you write the code, explain how it works in plain English, pretend I’m a beginner developer.”

Or at any point in a session:

“Before you write the code, explain your plan, what files you’ll touch, what the overall approach will be.”

This second one is especially useful for complex changes. If Claude Code’s plan sounds wrong to you, you can redirect before any code is written.

Prompt Patterns That Work

Here are specific prompt structures that consistently produce excellent results:

The “Context + Goal + Constraints” Pattern

[Context: describe the current state]
[Goal: describe the desired outcome]
[Constraints: technical or stylistic requirements]

Example:
"Our checkout form currently collects name, email, and address.
I want to add a phone number field that is optional.
The field should validate that the input is a valid phone number if provided, and we should use the same input component style as the existing fields."

The “Negative Space” Pattern

Tell Claude Code what to avoid:

“Add a caching layer for our API responses. Do NOT introduce any new dependencies, use only what’s already in our package.json.”

“Refactor this function to be more readable. Do NOT change its behavior or its interface, existing callers should not need to change.”

The “Scope” Pattern

When you want a focused change, explicitly bound it:

“Only look at the src/components/Header.jsx file. Don’t change anything else. Make the navigation links highlight when the current page matches.”

The “Thinking Out Loud” Pattern

For complex architectural decisions:

“I want to add real-time notifications to our app. Before writing any code, think through the options, we could use WebSockets, Server-Sent Events, or polling. Given that we’re on a serverless platform, explain which approach makes most sense and why.”

This produces a deliberate reasoning process rather than the first implementation that comes to mind.

Multi-Turn Conversations

Claude Code is not a single-shot tool. Some of the best work happens over multiple turns:

Turn 1: "I want to add user authentication to this app. What are the main
         things we need to implement?"

[Claude Code responds with a list: password hashing, session management,
login endpoint, registration endpoint, protected routes…]

Turn 2: "Let's start with user registration. Implement the registration
         endpoint and the password hashing."

[Claude Code implements…]

Turn 3: "Good. Now run our test file (! npm test) to make sure we haven't
         broken anything."

[Tests run, output shows…]

Turn 4: "The test for the user model is failing, the error is [paste error].
         Fix it."

This is how real development works. Not one big prompt, but an ongoing dialogue that iteratively builds toward the goal.

Prompts to Avoid

Just as valuable as knowing what works is knowing what does not:

Vague directives: “Make this better.” Better how? Faster? More readable? More secure? Be specific.

Too many things at once: “Add user authentication, redesign the homepage, fix the search bug, and add PDF export.” Pick one thing. Doing too many things in a single prompt produces muddled output and makes it hard to isolate problems.

Prompts without context in a fresh session: “Fix the bug in the user model.” What bug? Which file? Claude Code has not read your code yet.

Emotional framing: “This is terrible, please fix everything.” Claude Code does not have feelings (in any meaningful sense), but vague negative framing does not give it actionable direction. Say what you want, not how you feel about the current state.

The Feedback Loop

One of the most powerful things you can do is close the feedback loop by having Claude Code verify its own work:

“After you make the change, run ! npm test and show me the results.”

“After building the form, open a quick server with ! npx serve . and tell me the URL so I can test it.”

“Check if there are any obvious issues with the code you just wrote before I test it.”

That last one, asking Claude Code to review its own output, catches a surprising number of issues. It is not infallible, but it adds a quality gate with zero effort on your part.

Giving Good Feedback

When Claude Code produces something that needs adjustment, your feedback prompt is its own kind of craft:

Imprecise feedback: “This doesn’t look right.”

Better feedback: “The layout looks wrong, the button is appearing on its own line but it should be inline with the text input, side by side.”

Best feedback: “Here’s a screenshot of what I see [description or file], and here’s what I expected. The button should be to the right of the input on the same line, not below it. Can you fix the CSS?”

The more specific and visual your feedback, the more precisely Claude Code can target the fix.

The “Staff Engineer” Prompt

This is one I use regularly when I want the highest quality output:

“Approach this as a staff engineer who cares deeply about code quality, maintainability, and avoiding over-engineering. [Then your request.]”

Or even more specifically:

“Before writing code, think about whether there’s a simpler approach that achieves the same goal. I’d rather have 10 lines of boring code than 50 lines of clever code.”

The Claude model responds to framing. Invoking quality-conscious, experienced-developer framing tends to produce exactly that kind of output.

If this chapter was useful, the rest of the book goes deeper: how to structure CLAUDE.md files, when to trust Claude Code’s judgment versus your own, and how teams are changing their workflows around it entirely.

Get Think. Prompt. Create on Amazon →

Until next week, write your next prompt like you’re briefing a senior engineer, not filling out a form.

— Aarron & Eli

If you’re not already a Design Better paid subscriber, get 20% off an annual subscription and get access to all our Portfolio Club events and recordings. You’ll also be invited to the Design Better Slack community where you’ll find great designers and past guests on the show providing design advice.

20% off annual subscription

Thank you to Jalen Igbeare and Tom Grimm for sharing their portfolios.

And thank you , , , , , and many others for tuning our live video with and !

In 2011, I came into Silicon Valley as a bit of an outsider. Up to that point, I’d worked at small companies designing physical products like underwater camera equipment, and then started an underwater photography magazine. Neither was a big moneymaker (surprise!), so after our daughter was born, I thought I’d try my luck in the software design world.

My first interview, a year prior at a quickly growing and now notorious company I won’t name, was an immediate culture shock.

“You should wear a suit,” my wife told me.

“No, too formal. I’ll wear a sport jacket and jeans,” I replied, full of my perceived wisdom.

When my first interviewer showed up looking like he’d slept under his desk, with basketball shorts, dirty gym socks, and no shoes, I knew I’d never get the job.

But I was determined to figure it out, and by the next year I got into a startup accelerator at the venture capital firm Innovation Endeavors. Eric Ries had just published The Lean Startup, and everyone in the SV ecosystem was quoting it. MVP (minimum viable product), the pivot, build-measure-learn: this terminology became the operating language of the startup world.

The words were useful but overused, and I like to think I was a little ahead of the curve when I designed some t-shirts poking fun at them in 2013. (HBO’s parody Silicon Valley wouldn’t come out until the following year.)

The most important product you’ll ever design

What struck me even then was how much of the Lean Startup methodology paralleled the human-centered design thinking I’d been trained on at Stanford: iterate fast, work with users, learn from failure, build empathy.

That overlap, it turns out, was no accident. Eric’s new book, Incorruptible: Why Good Companies Go Bad and How Great Companies Stay Great, is his reckoning with what happens after you build something great. A surprising amount of it speaks directly to designers. We talked with Eric about why speed was never the real problem, why the value a company creates comes from the design of its products, and why the single best way to use AI might be to refuse to let it do your work for you.

Listen to the episode

Eric Ries: Spotify, Apple Podcasts, Substack, Youtube

Already a paid subscriber? Follow this link to set up you premium feeds on Apple, Spotify or any other platform from your phone or computer.

Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain.

$100 off the event for those who book their own accommodation. Use code DBFRIENDS at this link:

Reserve your spot →

A second code for $15% off (also offsite accommodation) is available for Design Better premium members. Link and code after the paywall below at the bottom of this post.

Design thinking as the bridge

One of the things I most wanted to ask Eric about was the parallel between lean startup and design thinking. His answer was that the bridge was deliberate. He’d studied design thinking closely, and built relationships with its leaders, precisely because he’d noticed how much these allied disciplines distrusted one another:

“The agile thinking people and the scrum people and the design thinking people didn’t get along, and the scrum people and the DevOps people didn’t get along. I feel like there were all these people who I consider we should be natural allies fighting with each other because we have our own tribal identities and our own separate cultures.”

What lean startup offered, in his telling, wasn’t a new methodology so much as a shared language. It was a way for people who care about craft to be heard in rooms where the only accepted currency is ROI:

“If you ever tried to convince an executive that they should care about story points or burndown charts, even development velocity charts — let alone, God forbid, design integrity — good luck, right? Because they’re stack ranking by ROI. And you’re in there being like, let me explain to you why rounded corners are better for skeuomorphism. Like, what are you talking about?”

The consequence, Eric argues, is that the people who care about quality — designers, engineers, anyone with a craft — get pushed to the edge of the business conversation, their concerns treated as “parochial or almost a little bit juvenile.” And he thinks that’s exactly backwards:

Read more

Fifteen years ago, Eric Ries handed a generation of founders a playbook. When Eli was in a Palo Alto-based startup accelerator in 2011, The Lean Startup felt like the only book anyone in that ecosystem was talking about. It was in the middle of a wildly optimistic moment for tech. Marc Andreessen declared that “software is eating the world,” social media was blooming, and there was a widespread belief that technology was about to democratize everything and bring us closer together. Concepts like the MVP (“minimum viable product,”), the pivot, and build-measure-learn became the operating language of Silicon Valley.

But a lot of the companies built on those ideas went on to get corrupted by forces Eric hadn’t yet named. His new book, Incorruptible: Why Good Companies Go Bad and How Great Companies Stay Great, is his reckoning with what happens after you build something great — and how to keep it from falling apart.

Buy the book

In this conversation, we get into why speed itself wasn’t the problem, but treating a rising stock price as proof of health is like assuming more exhaust means a faster car. Eric explains why doing the right thing 100% of the time is actually easier than doing it 98% of the time, and how companies behave like superorganisms with their own emergent character — a point he illustrates with a genuinely mind-bending study about ants solving a puzzle that no single ant ever could.

We talk about the “harder is easier” principle through stories from Patagonia and the long-term stock exchange he built as a design challenge, and why the value a company makes comes from the design of its products. And because we couldn’t resist, we get into AI slop, LLM psychosis, and Eric’s clear, simple antidote: never ask these tools to make you an artifact — ask them to teach you how to make one yourself.

Bio

Over the last two decades, Eric Ries’s ideas about continuous innovation, long-term thinking, governance, and market reform have reshaped company building and management practices. He is the creator of the Lean Startup method, and the author of the New York Times bestseller The Lean Startup; The Leader’s Guide; and The Startup Way.

As a founder, he has put his own ideas into practice with The Long-Term Stock Exchange (LTSE); Answer.AI, an AI R&D lab; the Lean Startup Co, which teaches and supports the implementation of Lean Startup; Virgil, a legal services startup; and IMVU, where the ideas that became the Lean Startup method were forged. On his podcast, The Eric Ries Show, he talks to guests including world-class technologists, thought leaders, and executives working to build profitable companies for the long-term benefit of society. Eric has served as an entrepreneur-in-residence at Harvard Business School and IDEO. He lives in the San Francisco Bay Area with his wife and three children.

Premium Episodes on Design Better

This is a premium episode on Design Better. We release two premium episodes per month, along with two free episodes for everyone. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

Premium subscribers get access to the documentary Design Disruptors and our growing library of books. You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show.

And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

Read more

When I was in college, I took a great printmaking class with the artist Enrique Chagoya. There were no assignments — he just taught various techniques, we’d present our work, and he’d offer a helpful critique afterward.

One of the many wonderful things about printmaking is the physicality of it: using a cutter to gouge out little strips of linoleum, inking the block with a roller, running it through the monotype press.

When pushing the gouge through block material, if your hand slips, you’ve ruined the line you spent twenty minutes sketching out. It’s slow. It’s a little dangerous (well, you can cut yourself). You can’t undo it. And that resistance is what makes the finished print feel like it came from somewhere. The mistakes can often make the finished work more interesting.

We tend to treat friction as a defect. Much of modern design has been about sanding it down: fewer steps, fewer decisions, less waiting. But the more I’ve made things by hand, the more convinced I am that friction isn’t the obstacle to meaningful work. It’s often the substance of it.

Carving a linoleum block with my daughter Phoebe around 10 years ago

That idea came up during our conversation with Ian Bogost, game designer, writer at The Atlantic, and author of the new book The Small Stuff. Ian has spent his career studying the designed life of ordinary things, and his book is essentially an argument for engaging with the small, textured, slightly effortful moments of daily life with curiosity and openness. It’s different than friction, though: he calls it gratification.

Listen to the episode

Ian Bogost: Spotify, Apple Podcasts, Substack, Youtube

Already a paid subscriber? Follow this link to set up you premium feeds on Apple, Spotify or any other platform from your phone or computer.

Join Eli and Aarron September 28–29 in Sonoma for the September Work(shop) Leadership Excursion — an intimate, conversation-first gathering of forty design leaders in the heart of wine country, built to challenge how you think about your craft and the coalitions behind it. Only a handful of tickets remain.

$100 off the event for those who book their own accommodation. Use code DBFRIENDS at this link:

Reserve your spot →

A second code for $15% off (also offsite accommodation) is available for Design Better premium members. Link and code after the paywall below at the bottom of this post.

Friction and gratification

Holding a warm, hand-thrown coffee mug in your hand. Sharpening a carpenter’s pencil with a pocket knife. We usually treat the moments of sensory satisfaction that Ian calls gratification as rare, something you have to work yourself into a special state of mind to access. Ian argues the opposite. They’re not scarce at all. They’re everywhere, and the only thing standing between us and them is attention.

“One of the things I try to do in the book is to reframe that idea of, call it mindfulness, or noticing, into something that’s more like acceptance — just accepting these sensory gifts that the world is always delivering to you. And that transforms them from something scarce into something excessive. There’s just a surplus of them all the time. If you miss one, it’s no big deal, because another one will arrive right at its heels.”

Read more

We’ve been to a lot of conferences over the years. You know the format: a speaker on a stage, a sea of seats, a hallway where the real conversations happen if you’re lucky enough to catch someone before they’re whisked away.

This isn’t that.

We’re partnering with our friends at September Works on the September Work(shop) Leadership Excursion, a two-day gathering of just forty design leaders in Sonoma this fall. The programming is intentionally conversation-first, which means the people you’ll hear from aren’t speakers who parachute in for a keynote and disappear—they’re part of the room. You’ll share meals with them, debate with them over a glass of Sonoma wine, and pick up threads from a morning session over dinner that night.

The theme: coalition building

Here’s the thing we keep hearing from design leaders: creating the design is often the easy part. Getting everyone behind it—your executive team, your cross-functional partners, the skeptics down the hall—that’s where it gets hard.

So we’re spending two days on coalition building, with voices from business, the arts, and politics who’ve done it in wildly different contexts:

Sheryl Cababa — Design strategist, founder of Optimistic Design, and author of Closing the Loop, on what a systems lens reveals about the art of bringing people together.

Bill Burnett — Executive Director of the Stanford Life Design Lab and author of Designing Your Life, on craft and meaning when the tools are changing this fast—and how to build something people want to be part of.

Molly Moon Neitzel — Founder of Molly Moon’s Homemade Ice Cream, who built a business and then used it to help change a city’s minimum wage policy. She’ll share who she had to bring together, who surprised her, and what didn’t work.

Paul Dichter — Writer and producer on Stranger Things, on what a decade inside that writers’ room taught him about turning colliding ideas into something greater than any one person could make.

Andy Allen — Founder of Not Boring Software, on building with conviction and how the community around his work shapes what he builds (and vice versa).

Andrew Evans — A designer-turned-magician, on the real-time trust that forms between a performer and a room full of strangers who’ve agreed to believe.

Why keep it small?

Because forty people can actually talk to each other. Small-group sessions and built-in community time mean you’re not collecting business cards—you’re building the kind of relationships that outlast the event. The whole thing feels less like a conference and more like a working session with people you genuinely want to think alongside.

And the setting doesn’t hurt. We’ll be at The Stavrand in Sonoma, with good food, a wine tasting excursion, a sit-down three-course dinner, and a few surprises we’re keeping under wraps.

The details

• When: September 28–29, 2026

• Where: The Stavrand, Sonoma, CA

• Who: Forty design and business leaders working to make design more impactful inside their organizations

• Tickets: Two options—$3,300 includes lodging at The Stavrand, or $2,200 if you’d rather book your own accommodation nearby. Both include all programming, meals, dinners, and the wine tasting.

Spots are genuinely limited (forty means forty), so if this sounds like your kind of room, don’t wait. We’ve already booked many of the tickets, with folks from Fortune 100 companies and brands you know and love.

We’ve got two discounts available for Design Better listeners and members.

The first is $100 off the event for those who book their own accommodation. Use code DBFRIENDS at this link:

Reserve your spot →

The second is $15% off (also offsite accommodation) for Design Better premium members. Link and code after the paywall below.

Need to make the case to your team? There’s a justification letter on the event page to help.

We miss seeing you in person. This is our excuse to fix that.

— Eli & Aarron

15% off tickets (book your own accommodation) for Design Better Premium Members

Read more

A few years ago, Ian Bogost wrote what he thought was a throwaway Atlantic piece about how electric vehicles would finally kill the manual transmission. It went off like a bomb — and the reaction told him people weren’t mourning a car part. They were mourning the feeling of dropping a gear into place, a small moment of sensory connection quietly disappearing without anyone choosing to give it up.

That feeling is the subject of his new book, The Small Stuff. Ian calls it gratification — distinct from happiness or satisfaction, it’s the immediate sensory delight of communing with ordinary things: the ridged coffee cup, the click of an elevator button, the tink of ice in a water bottle. And he diagnoses what he calls dematerialization: the slow way efficiency, automation, and software have severed us from the physical texture of daily life.

A game designer, longtime Atlantic contributor, and philosopher of the everyday at Washington University in St. Louis, Ian has spent his career — across books like Persuasive Games and Play Anything — arguing that the systems we build carry values whether we intend them to or not. Here he turns that lens on the ordinary objects most of us stopped noticing long ago.

For designers, this is becoming more and more relevant. Ian argues that somewhere between the mid-90s and now, user-centered design quietly mutated into outcome-oriented design — we kept the language of user experience while the goals drifted toward the organization instead of the person.

But this isn’t nostalgia or a plea for friction. Gratification, he insists, is easy. It’s already happening to you all the time. The designer’s job isn’t to add friction, but to notice where the sensory life has quietly drained out of the things we build, and to re-introduce it. And the challenge he leaves us with is deceptively simple: get curious.

The Small Stuff is out now. You can find Ian at bogost.com.

Bio

Dr. Ian Bogost is a writer, designer, and scholar of media and technology. He is the Barbara and David Thomas Distinguished Professor and Assistant Vice Provost at Washington University in St. Louis. At WashU, he is appointed in three colleges and the co-executive director of the Office of Public Scholarship.

Bogost is also a contributing writer at The Atlantic and the founding partner of Persuasive Games LLC, a game and design studio. He is the author of 11 books, most recently The Small Stuff: How to Lead a More Gratifying Life. Bogost’s award-winning games and artworks, which include Cow Clicker and A Slow Year have been played by millions of people and held in permanent collections around the world, including at the Smithsonian American Art Museum.

Premium Episodes on Design Better

This ad-supported episode is available to everyone. If you’d like to hear it ad-free, upgrade to our premium subscription, where you’ll get an additional 2 ad-free episodes per month (4 total). Premium subscribers also get access to the documentary Design Disruptors and our growing library of books. New premium subscriber benefit: we’ve launched a private Slack workspace…join now to connect with designers, product leaders & creative practitioners in our community.

And get a behind-the-scenes pass to every episode with The Roundup, where each week we bring you insights and actionable tactics from recent episodes.

You’ll also get access to our monthly AMAs with former guests, ad-free episodes, discounts and early access to workshops, and our monthly newsletter The Brief that compiles salient insights, quotes, readings, and creative processes uncovered in the show. And subscribers at the annual level now get access to the Design Better Toolkit, which gets you major discounts and free access to tools and courses that will help you unlock new skills, make your workflow more efficient, and take your creativity further.

Upgrade to paid

Visiting the links below is one of the best ways to support our show:

Masterclass: MasterClass is the only streaming platform where you can learn and grow with over 200+ of the world’s best. People like Steph Curry, Paul Krugman, Malcolm Gladwell, Dianne Von Furstenberg, Margaret Atwood, Lavar Burton and so many more inspiring thinkers share their wisdom in a format that is easy to follow and can be streamed anywhere on a smartphone, computer, smart TV, or even in audio mode. MasterClass always has great offers during the holidays, sometimes up to as much as 50% off. Head over to http://masterclass.com/designbetter for the current offer.

If you’re interested in sponsoring the show, please contact us at: sponsors@thecuriositydepartment.com

If you’d like to submit a guest idea, please contact us at: contact@thecuriositydepartment.com

Read more