Design Better

The Brief: Guide to communicating the value of design

Aarron Walter — Sun, 08 Nov 2026 12:01:00 GMT

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Communicating the value of design

By Aarron Walter

Ask designers why they’re left out of the decisions that shape their work, and you’ll hear the same answers: we’re downstream, they think we make things pretty, nobody understands what we do. Barry Katz, who wrote Make It New, a history of Silicon Valley design, hears it from former students now working in tech. Design, he told us (podcast), is “still a kind of a fragile presence in many companies”. It’s misunderstood, and underused as a tool businesses can use to drive adoption, improve retention, or increase margins. Design’s business potential is immense, so why is it still a struggle to get executives and colleagues to recognize its value?

Some of it is our doing. Designers are kept out of decisions because they often don’t describe their work as a competitive advantage. A strong understanding of business is required to communicate that.

We’ve talked to countless design leaders over the past decade about this topic. There are clear patterns. This guide collects evergreen advice that has worked for designers at companies like IBM, Google, Meta, Intuit, Wells Fargo, and more.

Creative Leadership Retreat: Paul Dichter

Eli Woolery — Wed, 04 Nov 2026 12:33:27 GMT

This episode kicks off a special series recorded live at our Creative Leadership Retreat in Sonoma, which we co-hosted with our friends at September Works in late September. We gathered 40 leaders from design, business, the arts, and politics for two days around the theme of coalition building.

Our first guest is Paul Dichter, who first came on Design Better for Episode 173 this past Spring. Most of us think of a coalition as something you build once. Paul had to keep one alive for a decade. He joined the Stranger Things writers’ room as a writer’s assistant in season one and left as co-executive producer at the finale, writing three of the show’s most memorable episodes along the way.

A video clip from our interview with Paul above; we’ll release the full video soon, subscribe to our Youtube channel to get it when it lands.

We asked Paul what he learned about moving ideas forward as a junior writer, before he had the authority to push them, and how conflict over creative direction gets sorted out. He tells the story of the final season, months of arguing and pitching under the weight of ten years of work, and a fanbase waiting for the ending.

Then the audience took over. Attendees, many of them leading creative teams of their own, asked what you do when a team loses its mojo and how you rally it back. They asked which personality types flourish in a collaborative room, and how you build alignment when there’s no clear user to test against.

They also asked how he sells a creative idea to people on the other side of the table, and how he made peace with the show ending after investing so much of himself in it.

This series is presented in partnership with September Works, a product design studio. They envision, evolve, and reinvent digital products. Learn more at september.works or reach them at hello@september.works.

The Roundup: What three years of AI workshops taught us

Eli Woolery — Fri, 30 Oct 2026 20:17:54 GMT

GenAI technology has been moving so quickly it’s easy to forget how weird it was when it all began. Way back in 2021, when dinosaurs still roamed the earth and X was still Twitter, I experimented with some early prompt-based image generation tools and got these bizarre (but at the time, oddly compelling) results:

As the tools got better, I got more and more curious about how they would continue to influence our work as designers and creatives. In the summer of 2024, my friend and colleague Bobby Hughes and I started running workshops to explore how these tools might integrate with the design thinking process: where did they work well, where were they counterproductive.

In this special edition of The Roundup, Bobby shares what we learned in those early workshops and how they evolved as we kept running them. We’re also previewing two workshops coming up next month—and one in the works—for anyone who wants to strengthen their creative confidence by researching, designing, and building with AI.

If you’re eager to jump straight to the workshops, learn more here:

AI x Influence for Design Researchers (next session Nov 17th-20th)
The Humans vs. AI (an ongoing free mini workshop)
Build with AI (two hands-on workshops for designers who want to build and ship functional prototypes and real software with AI)

We’re also wrapping up our 2026 State of Design Survey. Respond now to get access to the report when it comes out:

Staying human-centered in the AI era

by Bobby Hughes

When we started running AI x Design Thinking workshops in 2024, we were as new to AI as anyone else, so we were driven by our own curiosity as much as expertise.

In the early days of the AI boom, we saw a familiar pattern typical of many new technologies…an obsession with what the tech could do, (Make me a poem in a pirate voice! Generate an image of a baby with adult legs!) and what it could not do - including where it hilariously failed.

But given our human-centered bias, we were more interested in what designers might want AI to do for us. How do we use AI as a tool rather than a toy? How might it help us do better design work? Not just more faster, but how might it help us as designers be more human-centered, more compelling, more influential?

Maurice Cherry: Revision Path creator on why attention isn’t impact

Aarron Walter — Wed, 28 Oct 2026 14:38:28 GMT

For eleven years, Maurice Cherry made a weekly podcast called Revision Path showcasing Black designers from around the world. He recorded more than 500 episodes with designers on six continents and built a community around the show.

In 2019, the Smithsonian’s National Museum of African American History and Culture added eleven episodes to its permanent archives. And in 2025 the Eames Institute named him to its Curious 100.

Maurice never went to design school. He wanted to study English, but a STEM scholarship put him in computer science at Morehouse, where an advisor tol him the internet was a fad. He switched to math, graduated a semester early, and taught himself Photoshop from books he read in the aisles of a nearby Barnes & Noble. Years later, he was running his own studio with real clients and a payroll, and people still told him he wasn’t a real designer. So in 2013 he started Revision Path to show the work Black designers were doing.

We talk about growing up in Selma, Alabama, where civil rights history is part of the everyday landscape; what a math degree taught him about solving problems; and why Revision Path ultimately ended. Maurice explains how AI is speeding up problems the design industry always had, including the shrinking junior role, and argues that the modern designer has outgrown traditional design organizations.

Bio

Maurice Cherry is a designer, podcast producer, and commercial voice actor. From 2013 to 2024, he hosted Revision Path, a weekly podcast featuring Black designers from around the world. Eleven episodes are in the permanent archives of the Smithsonian’s National Museum of African American History and Culture. He also founded the Black Weblog Awards and ran the design studio Lunch. A math graduate of Morehouse College, he was named to the Eames Institute’s Curious 100 in 2025. Today he consults on podcasts and writes essays at mauricecherry.com.

Show notes

Books & Publications

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The Roundup: Lessons on typography from Tom Foley, Ellen Lupton, and Jonathon Hoefler

Eli Woolery — Fri, 23 Oct 2026 13:31:21 GMT

I began my career in physical product design, and apart from a few introductory studio design classes I took while studying product design as an undergrad (in what was technically an engineering major), I didn’t have much grounding in typography or graphic design.

Over the years I got more interested in it, and picked up books like Ellen Lupton’s Graphic Design: The New Basics. But it wasn’t until I decided to start an underwater photography magazine with a friend that I challenged myself to approach it more professionally.

By the time we went to print with the first issue, I was confident that the results were, as Larry David might say, pretty, pretty good. How wrong I was.

The first issue of Wetpixel Quarterly. The cover design was OK (although I didn’t realize the UPC code could be on the back!) but don’t look too closely at the typography inside 🙈

After sharing the print version with a friend who had studied graphic design in college,1 he pointed out several fundamental errors I’d made in typography and layout. First of all, the text across the columns wasn’t aligned to the grid. There were several other noob mistakes, but the one that, in retrospect, was the biggest missed opportunity was my choice of typefaces.

I ended up using what were essentially some of the default options in Adobe’s InDesign (Minion Pro and Myriad Pro). Not terrible, but not especially unique or creative either. Perhaps the equivalent of the non-offensive invitation your great aunt might send out for her dog’s 15th birthday. By the final issue, the design and layout had gotten better, but I’m sure there are still plenty of mistakes that better designers than me would point out.

In later years, as I continued to do graphic design work for clients both in print and on the web, I learned about resources like Jonathan Hoefler’s site (now Typography.com), which offered lovely type pairings.

Fast forward another few years, and we’ve been lucky enough to have some of these typography legends on Design Better: Ellen Lupton, Jonathan Hoefler, and most recently, Tom Foley.

In this issue of The Roundup, we’ll explore what we learned from these experts, and what you might apply to your own design practice, whether you’re a beginner, intermediate, or expert.

Listen to the episode

Tom Foley: Spotify, Apple Podcasts, Substack

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1. Pair by structure first, personality second

Most of us pair type by what we’ve seen before—a vibe we liked: I dig how this designer paired this serif with this sans. Tom’s advice is to ignore the vibe for a minute and look at the skeleton.

“There’s some really good principles that can make it a lot easier,” he told us. “And they’re actually looking at less expressive stuff and more structural things.”

One test is ancestry—tracing each typeface back to the tools that shaped it:

“Say you’ve got a serif headline typeface and it’s a modern or a Bodoni style, so has…high contrast, and the shoulders blend into the stems and it has fine serifs. That typeface model, that modern model, eventually evolved into grotesk typefaces… So those typefaces always pair better with grotesques because they have the same structure.”

Mid-century designers like Josef Müller-Brockmann used grotesk typefaces extensively in their work.

In other words, ask “what structural aspects of this typeface have come from which calligraphic tradition? Broad nib or pointed nib.” For a deep dive on that idea, Gerrit Noordzij’s The Stroke: Theory of Writing (1985) is the source of the “translation versus expansion” framework Tom alluded to.

The state of design in 2026

Aarron Walter — Thu, 22 Oct 2026 11:03:38 GMT

Is AI changing your job? Are you paid fairly for your role? Is design gaining influence at your company, or losing it?

Design and tech are changing dramatically. AI adoption has created a reckoning with our workflows, tooling, and teams. The role design plays inside companies is shifting, and many designers are uneasy about what comes next.

We want hard data on how much has changed. The State of Design Survey 2026 asks designers at every level about their work, their teams, and their careers. In November we’ll publish a report that shows:

How AI is changing the work: which tasks designers hand to AI, and how many now prototype or ship in code
Which tools designers rely on: the design and AI tools in regular use, and how they differ by role
Where careers are heading: layoffs, how long job searches take, and how confident designers feel about the next three years
Where design has a say: who design reports to, when it gets involved, and who makes the final call
What designers earn: salary ranges by role, experience, and region

The survey takes about 10 minutes. Your answers are anonymous and only reported in aggregate. Leave your email at the end and we’ll send you the full report free in November.

Take the survey

The more designers who answer, the clearer the picture gets for all of us.

Thanks in advance for contributing,

-Aarron and Eli

Tom Foley: How to pair typefaces and why the best brand fonts go unnoticed

Eli Woolery — Wed, 21 Oct 2026 11:16:32 GMT

Tom Foley didn’t set out to design typefaces. As a postgraduate student at Central Saint Martins in London, he was researching why Ireland, unlike Switzerland, the Netherlands, or Germany, never seemed to have a confident typographic voice of its own.

The answer led him through centuries of colonial history, to a so-called “Irish type” invented during the Reformation to make printed scripture look the way outsiders thought Irish readers would want it to look, and back further still, to fifth-century monks who may have given us the first true lowercase letters and the word space. The best response to that research, Tom realized, was a typeface. He called it Nib, and it now lives on Dublin’s heritage plaques.

That mix of deep research and hands-on craft has defined his career since. Tom worked on the first phase of Netflix Sans, a typeface you may see every day and probably never notice. At Monotype, he rose to Executive Creative Director and led custom work like the National Portrait Gallery’s contemporary serif. This year he walked away from that role to become Creative Type Director at Studio DRAMA, because he wanted to get back to making type.

We talk about how cultural context shapes letterforms, how to balance heritage with something that feels modern, and Tom’s practical framework for pairing typefaces, which starts with calligraphic roots and vertical metrics rather than vibes. We also get into why he left a prestigious executive role, how a childhood struggle with reading may have sharpened his eye for letters, and the books and typefaces he thinks every designer should know.

Bio

Tom Foley is Creative Type Director at Studio DRAMA in London, where he designs custom typefaces for brands. He was previously Executive Creative Director at Monotype, where his work included a custom serif for the National Portrait Gallery and his typeface Cotford. Before that, he spent years at Dalton Maag, working on multi-script projects for Nokia and the first phase of Netflix Sans. Tom came to type design through research: his postgraduate thesis at Central Saint Martins on Irish typographic history produced Nib, the typeface now used on Dublin City Council’s heritage plaques.

Short version: Tom Foley is Creative Type Director at Studio DRAMA in London and former Executive Creative Director at Monotype. His work spans custom typefaces for Netflix, Nokia, and the National Portrait Gallery.

Links:

Website (Studio DRAMA): studio-drama.com
Monotype Profile (archived): monotype.com/studio/tom-foley
LinkedIn: linkedin.com/in/tom-foley-75062158
Instagram: tom_foley_type

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The Brief: The essential setup for building web apps with AI

Aarron Walter — Sun, 18 Oct 2026 11:01:29 GMT

The Brief: The essential setup for building web apps with AI

By Aarron Walter

If you’ve been sitting on the sidelines, unsure how to start building software, held back by a limited understanding of how to set up the technical infrastructure for the app you want to make, it’s time to dive in. Knowing how to build working software with the help of AI is now expected in a growing number of roles.

The technical hurdles can feel daunting, but you don’t need a deep understanding of software architecture. Basic literacy is enough to help you understand the elements of building and maintaining an app with an AI collaborator, and it will widen your sense of what you can build.

Jenny Blackburn, who leads UX for Gemini at Google, said something on our show that stuck with us:

“In a lot of ways, the model is the material that we are designing with. And the more you understand the material, the more you can innovate with it.”
Jenny Blackburn, VP of UX, Google Gemini

Design’s medium is changing. We still work in tools like Figma, Photoshop, and Illustrator, but AI extends our workflow into working code, where an idea becomes something people can use.

This guide will help you get your bearings, set up a project, and ship a working product.

Kevin Flores: Find Your Inner Rebel

Eli Woolery — Wed, 14 Oct 2026 14:20:49 GMT

Kevin Flores has been part of the Design Better community for years — we first met him in 2017, while he was leading design at 23andMe, back when we were researching how design teams are structured for the Design Genome Project. So it’s a real pleasure to finally have him on the show to talk about his new book, Find Your Inner Rebel.

The book is built around what Kevin calls his punk rock formula for career reinvention: resistance plus resilience equals reinvention. But don’t mistake the attitude for advice to quit your job. Kevin is candid that sometimes the smartest move is to hunker down, keep working toward change from where you are, and be ready when it comes, whether you choose it or it’s chosen for you.

Get the book

We talk about why strong generalists struggle to get hired (and how to fix it), why your personal brand matters more than ever when you’re competing against hundreds of applicants, and a simple test for your portfolio’s opening statement: swap in someone else’s name and photo and see if it still works.

As Kevin puts it, “you are the unique thing in the equation.” We also get into misalignment burnout, why designers should look beyond big tech to places like local government, and servant leadership.

Bio

Kevin Flores is a design leader, mentor, and author of Find Your Inner Rebel. He has built and led product and design teams in every work environment: agency, freelance, startup, and mid-to-large companies, including Verizon, 23andMe, and LinkedIn. He and his wife Jeanine met as design undergraduates at the University of Illinois and went on to co-found an interactive agency in Silicon Valley in the 1990s, and together they co-wrote the Design Career Handbook. Kevin spent six years as a mentor in First Round Capital’s Fast Track program, and serves as an industry advisor for design and user research for the Mission College Design and Diablo Valley College Digital Media joint advisory board. Learn more at innerrebelbook.com.

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How Milton Glaser set design quality standards

Aarron Walter — Fri, 09 Oct 2026 20:51:34 GMT

In graduate school, Randy Hunt spent weeks on a poster for Milton Glaser’s class. He built an image entirely from hand lettering, so it read as a picture from across the room and as words up close. Glaser pointed at it and said, “Well, that’s not very good,” and moved on to the next student.

Ouch! Randy tells the story fondly. He went on to apprentice in Glaser’s studio, then led design at Etsy, Grab, and Notion, and he chairs the MFA Design program at the School of Visual Arts. Glaser played a huge role in shaping Randy’s sensibility as a designer, and his standards for quality.

Eli and I talked with Randy about what that standard looks like inside a software company. His answers apply whether you lead a team or want to join a better one.

Listen to the episode

Randy Hunt: Spotify, Apple Podcasts, Substack

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Set a high bar and good people get better

Quality standards are often framed as a bar to aspire to, but Milton Glaser had a quality floor, a baseline of excellent he expected from his studio and from his students. Randy compares it to teaching to the top of the class.

Randy brings the same approach to his own teams. Put five or six excellent designers together, especially ones who keep their egos in check, and each of them improves faster than they would alone. Everyone’s work raises what the others expect of themselves.

“Keep the floor really high so that the ceiling can get higher.”
—Randy Hunt

Dan Harden described the same kind of mentor when he told us about working for George Nelson. Nelson, he said, “was always striving for the apotheosis, the very best you can do,” and he refused to compromise on the design while others argued about cost. Both Dan and Randy describe a mentor whose standard became their own.

George Nelson is regarded as one of the most important figures in American design. Active as an architect, a product and exhibition designer and a writer, he was a leading voice in the discourse on design and architecture over several decades.

“The objective should be to keep improving one’s basic product.”
—George Nelson

Glaser was generous as well as demanding. Randy calls him a “communication philosopher” who cared about how people feel about things. He remembers the bowl of fresh fruit Glaser kept in the studio, gesture of hospitality to all who visited the studio.

Randy Hunt: Notion and Etsy design leader on why the best design teams stay small

Eli Woolery — Wed, 07 Oct 2026 11:34:36 GMT

In graduate school, Randy Hunt poured his heart and soul into a poster for Milton Glaser’s class, a picture built entirely from hand lettering that read as an image from across the room and as words up close. Glaser glanced at it, said, “Well, that’s not very good,” and moved on to the next student.

Randy tells that story fondly. What stayed with him wasn’t the sting but the standard: keep the floor high, and the ceiling keeps rising. He carried that idea from Glaser’s studio, where he apprenticed, through a career leading design at Etsy, at Grab in Singapore, and until recently at Notion.

At Notion, that standard meant a design team smaller than anyone would expect, on purpose. Randy argues that limited bandwidth forces a company to prioritize, and that great people have little patience for what he calls “the work around the work.” The team doesn’t talk about titles or levels. Designers ship code in the production app, something Randy built teams around at Etsy in 2010, long before “design engineer” came back into fashion.

We also get into what he calls “whole design,” which means treating a push notification with the same care as the main dashboard. He explains why hotels and restaurants inspire him as much as any software, and traces that back to growing up near Disney’s carefully spaced trash cans in Orlando and to the bowl of fresh fruit that always sat in Glaser’s studio.

Bio

Randy J. Hunt is a designer, artist, and author based in New York City, with more than 20 years of experience building products, brands, and businesses. Most recently, he was Head of Design at Notion. He also chairs the MFA Design program at the School of Visual Arts, a graduate program focused on entrepreneurial designers. Earlier, he led design at Etsy, Artsy, and Grab, co-founded the designer-made marketplace Supermarket, and served as Chief Product Officer at the coffee-tech company Morning. He apprenticed at Milton Glaser's studio, founded the design studio Citizen Scholar, and wrote Product Design for the Web (New Riders, 2013).

Books & Links

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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 4 ad-free episodes per month. 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.

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Introducing the new DesignBetter.com

Aarron Walter — Tue, 06 Oct 2026 18:17:51 GMT

Design Better has a new website at DesignBetter.com. We hope you’ll take a look, and bookmark it so you can find everything we publish.

Visit DesignBetter.com

Everything in one place

We publish on Substack, YouTube, and podcast apps, which made it hard for subscribers to find everything we offer. The new site brings it together. On our new site you'll find our Substack posts, YouTube videos, and podcast episodes, along with our job board, books, and more.

Corpus Search

We built Corpus, a searchable archive of every podcast episode, video, book, and article Design Better has published. Search for any topic, and Corpus shows you everything we've released about it. It's built into the new site.

Subscription management is not changing

Substack has hosted much of our work for several years, and it still manages your free or paid subscription. Our newsletters will still come from Substack. You don't need to do anything. Your podcast feed hasn't changed either.

Feedback

If you have feedback, find a bug, or just want to say hi, email us at contact@thecuriositydepartment.com.

Thanks for being a subscriber and part of the Design Better community!

-Eli and Aarron

Matt Owens: Athletics co-founder on keeping your creative fire lit

Aarron Walter — Fri, 02 Oct 2026 22:41:34 GMT

When Aarron was fresh out of grad school, working at an agency outside Philadelphia, he and his coworkers used to crowd around a monitor to study volumeone.com. Most websites back then had a picture, maybe an image map. Matt Owens’s site had 3D, animation, and experimental graphic design, and none of us could figure out how he made it.

Matt launched Volumeone.com in 1997, and it now sits in SFMOMA’s permanent collection. Before that, he was a skater and punk kid from Texas who ran a record label with his twin brother, then went to Cranbrook and landed in New York just as the web took off. In 2004, he and a few friends rented an old boxing gym in Williamsburg and kept the word on the door: Athletics. Today it’s a 30-person brand studio working with Google, IBM, Stripe, and Major League Soccer.

We talked with Matt about how punk rock taught him to start things without overthinking them, what designers lost when Flash died, and how Athletics grew from a punk house into a proper agency. He explains why he calls himself the studio’s most capable intern and still takes on projects of his own to keep his skills sharp.

We also get into how his team uses AI as one ingredient rather than the whole recipe, and why good creatives can smell polished slop. We wrap up with his book, A Visible Distance, and the rebel optimism he passes on to his students at SVA.

Bio

Matt Owens is co-founder and Chief Design and Innovation Officer at Athletics, a Brooklyn brand studio whose clients include Google, IBM, Stripe, Square, and Major League Soccer. He holds a BFA from UT Austin and an MFA from Cranbrook Academy of Art. From 1997 to 2009 he self-published the experimental design quarterly Volumeone.com, now in SFMOMA’s permanent collection. He is the author of A Visible Distance: Craft, Creativity, and the Business of Design (Set Margins, 2024), teaches at the School of Visual Arts, and writes on Substack. He lives in Brooklyn with his family.

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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.

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The Roundup: How to defeat jargon, win over a pushy PM, and fix the collaboration gap

Eli Woolery — Sat, 26 Sep 2026 14:40:37 GMT

Cataplasm. Athanor. Estoppel.1 If you know the definition of these words without having to lean on Wikipedia or another source, you’re probably either a linguist or really good at Scrabble. The terms are, respectively, jargon from the fields of medicine, alchemy, and the law in the 1650’s.

KPIs. Synergy. Stakeholders. Over 350 years later, we have our own jargon to wrestle with, terms that sometimes have real meaning, but are often just inserted into our daily conversations with our colleagues to avoid getting specific, or to sound authoritative.

Our guest this week, Blaine Billingsley, is a staff designer at OpenAI who is openly allergic to the kinds of jargon we often run into in the tech world. He studied comparative religion in college, and while reading ancient texts, had to try to understand the real meaning of the words, as well as all of the ways people might interpret it. So he finds it counterproductive to use terms that are ambiguous.

In our conversation with Blaine, we learned why designers should be at the forefront of the battle against jargon. We also learned how to win over a pushy PM, what design work actually looks like inside OpenAI, and why more experience doesn't always get you better results from AI.

Listen to the episode

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The battle against jargon

Blaine traces his allergy to vague terms straight back to those ancient texts:

“If I do have a unique quality, like personally in my career, I think it is that I’m just like really allergic to jargon phrases. And I do think actually part of that comes from studying religion where you’re reading a lot of ancient texts and you’re like, what does this really actually mean?”

The movie Office Space captured the absurdity of jargon in the corporate world...

Jargon sounds silly, but that isn’t the real problem. The real problem is that it lets everyone off the hook. “I find corporate jargon in particular, but any kind of jargon just obfuscating and disempowering,” he told us. “I think it’s a way for us to not get specific.”

Every company he’s worked at has built up its own dialect of “things that are kind of always okay to say,” and those phrases, he says, “always shut down deeper thought.” Blaine thinks designers are the right people to call that out, because the user is literally our job:

Blaine Billingsley: OpenAI designer on the collaboration problem AI hasn't solved yet

Eli Woolery — Wed, 23 Sep 2026 13:01:42 GMT

Blaine Billingsley is a staff designer at OpenAI, and his path there was anything but a straight line. He studied music composition and comparative religion, played guitar in Texas for a living (he remembers checking his bank account, seeing seven dollars, and feeling pumped), then drove to San Francisco and took a data entry job at a startup. The engineers taught him to script his way through the work in a couple of hours, and he spent the rest of the day learning from them. From there he went on to companies big and small, including a long run on Gmail.

Blaine has an allergy to corporate jargon that we found interesting. He’s known amongst his colleagues for rewriting product specs to get absolute clarity on a project, and for raising his hand in meetings to ask, “what do we really mean by ‘create a command center for work’”.

We talk about why a design principle only helps if you could reasonably disagree with it, and his counterintuitive advice for working with a pushy PM: the best way to have influence is to be influenced.

Then we get into how design actually works inside OpenAI. Blaine walks us through what goes into an eval, and the product design plugin he built with one engineer, whose biggest fans turned out to be the PMs and engineers who were starved for a design partner.

Bio

Blaine Billingsley is a member of the design staff at OpenAI, where he works on making ChatGPT a daily tool for designers and built a product design plugin focused on translation workflows like image-to-code. Before OpenAI, he was a Product Design Architect at Slack and a Staff Experience Designer at YouTube, and earlier held design roles at Airbnb, where he created a system of Host Guides, and Google, where he worked on Inbox by Gmail.

He was also the sole designer at Pattern Technologies, an AI-powered sales startup acquired by Workday. Blaine studied music composition and comparative religion, played guitar professionally in Texas, and got his start in tech doing data entry at a San Francisco startup. He's known for his allergy to jargon, his love of a clear process, and his belief that a designer's job is to represent the user.

Books & links mentioned

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The Brief: 7 Principles for better AI collaboration

Aarron Walter — Fri, 18 Sep 2026 11:51:47 GMT

I asked nine AI agents how to work with them better. They schooled me.

By Aarron Walter

Designing and building software has been the center of my working life for twenty-five years. But in the past year I’ve designed and built more software than in the previous twenty-five combined, because AI is now my collaborator.

Early in my career I learned that working across disciplines has a steep learning curve. I struggled to collaborate with some of the engineers on my teams. But after getting to know them—how they thought, what they valued, their workflow—we started to find some common ground. I had to learn how to be a better partner to them.

I’m relearning that lesson now as I work with AI. It’s equal parts amazing and frustrating. Often agents won’t follow the specifications in my design systems, they’re prone to building elaborate solutions to simple problems, and don’t get me started on how opaque and verbose their communication can be.

These complaints sound awfully similar to the ones I had back in the day when I was working side-by-side with engineers. I solved those problems by getting to know my collaborators better. Maybe that approach could work here too?

So I interviewed all nine of the AI agents I’ve been regularly working with on projects of every size, and asked each one the same two questions:

What lessons have you learned from this project that you would take forward to make future work higher quality and more efficient?
What guidance do you have for me to help me communicate more effectively on projects going forward?

Even though each agent was working on a different project, and none of them were privy to one another's experience (ahem, that I know of), patterns emerged. They gave me a performance review that extrapolated into 7 principles that can be applied on any AI collaboration project.

Before we jump into the principles, if you’re already working on projects with AI, I encourage you to ask your agents these same questions. You’ll get your own guidance that will help you work more efficiently and reduce frustrating miscommunications.

An AI collaboration toolkit

At the end I’ve put everything their answers taught me into a kit you can download and use today:

A prompt that makes an AI agent interview you before it starts building.
A project brief template that will help you communicate clearly to agents when you start a new project.
An installable skill that runs the whole thing automatically.

7 Principles for better AI collaboration

A quick note first. These agents were building software, but none of the principles are about code. They work the same way when you’re asking for a research synthesis, a strategy memo, a lecture plan, or a hiring rubric. If you’ve never opened a code editor, all these principles will still help your work.

Mack Paul: Co-author of Miracle Road on designing places where innovation happens

Aarron Walter — Thu, 17 Sep 2026 09:11:44 GMT

In the mid-1950s, North Carolina was one of the poorest states in the country. Its economy ran on tobacco, furniture, and textiles — all three in decline — and its universities were turning out talent that promptly left for somewhere with better jobs.

Today the stretch of pine woods between Raleigh, Durham, and Chapel Hill is the largest research park in the United States. The barcode came out of it. So did AZT, ultrasound, and AstroTurf.

Our guest Mack Paul spent years working out how that happened. He’s the co-author of Miracle Road, a history of Research Triangle Park (known as RTP) written with his father — a journalist — and built on about 160 interviews with the scientists, planners, and politicians who were there. It’s out October 6th.

Hundreds of research parks have been attempted, and most failed. RTP started later than Silicon Valley or Route 128, with no defense money, no entrepreneurial culture, and universities that were openly uneasy about mixing academia with industry. But it worked anyway.

Mack’s answer to why is not what you might expect. The park itself was almost an afterthought. What made it work was a set of long, unglamorous commitments: a governor who went industry hunting, a community college system that promised to train any company’s workers for free, and a decision about desegregation that made North Carolina a better bet than Virginia — which is a big part of why IBM came in 1965.

We talk about what made it take off, the challenges now as RTP tries to become something denser and less car-dependent, and what it takes to build a place people actually want to be. We also talk about what it’s like to write a book with your father.

Bio

Mack Paul is a founder of Morningstar Law Group in Raleigh, where he has spent 30 years on the legal and political machinery behind how places get built — zoning, land use, environmental permitting, public-private partnerships, and public financing for infrastructure, mostly on large mixed-use and urban infill projects in North Carolina’s Triangle region.

He’s a LEED Accredited Professional and served six years as the public member of the NC Building Code Council. He sits on the NC State Design Guild board, has advised the modernist preservation nonprofit US Modernist, helped organize the “Build Raleigh Better” symposium, and co-founded a development company aimed at raising design quality in the region. He teaches Real Estate Development Law at NC State.

Mack is the co-author, with his father, of Miracle Road: The Story of Research Triangle Park, published by Duke University Press.

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The Roundup: Why some of Google's best designers spent time as PMs

Aarron Walter — Mon, 14 Sep 2026 19:56:01 GMT

Researchers are prototyping. Designers are shipping code. PMs are building working demos. Every role on a product team is absorbing skills that used to belong to the role next door, and AI is doing most of the folding.

And yet designers still spend too much time explaining what they do (ahem, do engineers and PMs have to do this?).

How many times have you explained design to someone who was never going to be persuaded by an explanation?

Explaining the value of design is a dead end. Let’s stop trying. Nobody comes to respect a discipline through hand waving explanations. There’s a softer, more effective approach. Go work inside another role for a while. You learn how your colleagues think, what’s important to them, and the challenges holding them back. You will become an ambassador for design without pitching.

I’ve seen this happen at Google. Despite employing more designers than any other company on Earth, Google is still an engineering led company. Design can often feel like an outsider.

As a contractor with Google, I met designers across many of its teams. The ones with the most influence had almost all spent time as a product manager. They came back with a sharper view of the business and of how their colleagues work, and with alliances that made every cross-functional project easier afterward. Their careers moved faster for it.

Listen to the full conversation with Niyati Gupta on Spotify or Apple Podcasts.

Niyati Gupta took that path. She earned a design degree inside one of India’s largest engineering institutes, at a time when, in her words, “nobody understood what it was.” Next she went to Carnegie Mellon to research health information for low-literacy users in rural India. Then on to Autodesk, building molecular visualization tools for scientists. And at Google she worked on truly inspiring projects on the Next Billion Users team. These days she’s at Netflix, where she designs commerce and partnerships.

“I call my career one long experiment of trying new things, experimenting, failing, learning, and putting myself in uncomfortable situations and just being okay with that.”

She has a name for the pattern. “I call them my personal learning loops.” The biggest one took her out of design entirely, and it taught her where influence comes from. It’s not from a title, but from relationships and the experiences you share with cross functional colleagues.

Her career path has lessons for all designers struggling to be relevant in their org and build a career they can be proud of.

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 →

1. The Google approach, try being a PM

Google has a unique PM rotation program that builds relationships and skills.

Federico Casalegno: Samsung EVP on how 20,000 years of creativity shapes design today

Eli Woolery — Thu, 10 Sep 2026 11:13:41 GMT

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.

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The Roundup: Staff product designer on getting used to change

Eli Woolery — Fri, 04 Sep 2026 12:42:19 GMT

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.