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364 posts tagged with “product design”

Cat Wu, Anthropic’s Head of Product for Claude Code, describes the hiring filter on her team in her interview with Lenny Rachitsky:

I think all of the roles are merging. PMs are doing some engineering work. Engineers are doing PM work. Designers are PMing and also landing code. You can either hire a lot more engineers who have great product taste, or you can keep your engineering hiring the same and hire a lot more PMs to help guide some of their work. On our team, we’re pretty focused on hiring engineers with great product taste. This way we can reduce the amount of overhead for shipping any product. Like there are many engineers on our team who are fully able to end to end go from see user feedback on Twitter through to like ship a product at the end of the week with almost no product involvement. And this, I think, is actually like the most efficient way to ship something. So I think like engineer and PM are kind of overlapping and you will get a lot of benefit from having more of either. I think product taste is still a very rare skill to have and we’ll pretty much hire anyone who we feel has demonstrated this strongly.

This is what the Full Stack Builder pattern looks like as a hiring filter. The headline is the merging of roles. Wu’s own background says where the bench comes from:

Yeah, I was an engineer for many years. I was then a VC very briefly before joining Anthropic. And actually almost all the PMs on our team have either been engineers or ship code here on Claude Code. And so that’s one of the things that I think helps build trust with the team and also just enables us to move a lot faster. And then actually our designers also have been front-end engineers before.

So to be clear, Wu doesn’t say that the roles have merged, but what she’s describing is the continued blurring of lines.

How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)

Cat Wu is Head of Product for Claude Code and Cowork at Anthropic, building one of the most important AI products of this generation. Before joining Anthropic, Cat spent years as an engineer and briefly worked in VC. Today, she’s interviewing hundreds of product managers who are trying to break…

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Maggie Appleton, staff research engineer at GitHub Next, wrote up her recent talk on agentic AI productivity. (Video here if you’d rather watch.) Her central claim comes early:

I call it this “one man, a two dozen claudes” theory of the future. The pitch here is that one person with a fleet of agents will do the work of an entire team of developers. The main problem with this dream is it assumes software is made by one person. All these tools are single player interfaces. […] Software is not made by one person in a vacuum. It’s a team sport. Everyone building it needs to agree on what they’re building and why.

The single-player critique is the missing piece in most AI productivity takes. Most demos of a coding agent show one engineer at a terminal. Designers face the same situation with AI prompt-to-code tools. Collaborating isn’t as easy as sharing a Figma link. That’s the actual gap in current tooling, and it’s downstream of the single-player assumption.

Appleton’s second move:

Implementation is rapidly becoming a solved problem, right? Writing code is now fast, it’s getting cheap, and quality is going up and to the right. The hard question is no longer how to build it. It’s should we build it. Agreeing on what to build is the new bottleneck. […] When production is cheap, opportunity cost becomes the real cost. You can’t build everything, and whatever you pick comes at the cost of everything else.

When production is cheap, picking what to make becomes the whole job. The cost difference between two engineering paths is now nearly zero, so the choice between them carries all the weight. Teams that miss this will end up shipping volume and mistaking it for productivity.

A talk like this could be about tooling, and Appleton does walk through Ace, GitHub Next’s prototype multiplayer workspace, in some detail. But the more important argument is about what you do with the hours you free up. Going faster is not the prize. Appleton:

We have an opportunity to not just go faster and build a giant pile of the same crappy software. But instead to make much better software through more rigorous critical thinking and better alignment in the planning stage. By doing more exploration, more research, and thinking through problems more deeply than we could have before.

The reclaimed hours are an opportunity, but they are also a test. Do you spend them shipping more, or do you spend them shipping better? The first answer gets you the giant pile. The second takes work the agents cannot do for you.

Appleton closes on craft:

Many people are now realising that in a world of fast, cheap software, quality becomes the new differentiator. The bar is being set much higher. Craftsmanship is what will set you apart from the vibe-coded slop. But craft still costs time and energy. It is not free, and in order to buy the time and energy for it, you need to do fewer things better, which requires strong alignment.

Title card for "One Developer, Two Dozen Agents, Zero Alignment" — a talk about collaborative AI engineering and a tour of Ace, the multiplayer coding workspace.

One Developer, Two Dozen Agents, Zero Alignment

Why we need collaborative AI engineering and a tour of Ace: the multiplayer coding workspace

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Andy Matuschak describes two accidental tyrannies that have shaped software for forty years: the application model that traps software in one-size-fits-all packages, and programming as a specialization that crowds out non-programmers from inventing interfaces. He thinks coding agents could break both, and he’s already seeing it happen with the designers he works with:

I’ve been seeing it. I spent 2025 collaborating with two talented designers. Their story with coding agents this past year has been truly wild. I think the impact on my collaborators has been much greater than the impact on me, despite the fact that I’m now building perhaps ten times the speed.

Unlike me, these two started their careers in design and spent their formative years in the arts culture. They can program a bit, but the process was really slow and difficult enough to pose a significant barrier. At the start of 2025, coding models could implement small one-off design ideas—but their outputs would just fall apart after a couple of iterations. By the end of the year, my collaborators were routinely prototyping novel interface ideas and sustaining that iteration across weeks.

“The impact on my collaborators has been much greater than the impact on me.” Matuschak is moving ten times faster, and he still thinks his designers are the ones whose careers just turned over. That observation is rare from the person on the receiving end of the bigger gain in raw output.

Matuschak’s diagnosis of why the old arrangement was such a trap for designers:

Non-programming designers are trying to invent something in an interactive medium without being able to make something meaningfully interactive. So much of invention is about intimacy with the materials, tight feedback, sensitive observation, and authentic use. So it’s a catch-22: to enter into proper dialogue with their medium, a non-programmer needs to get help from a programmer. That generally requires the idea to be at least somewhat legible and compelling. But if they’re doing something truly novel, they often can’t make it legible and compelling without being in that close dialogue with their medium.

The old design-engineering separation trapped designers in a less obvious way. They often couldn’t even tell whether their ideas were brilliant, because they couldn’t get their hands on the material to find out. You can’t iterate on a feeling. You have to push something around until it pushes back. For most of my career, designers did that pushing in flat mockups and click-through prototypes, working through dynamic behavior they had never actually felt. Of course the technical ideas fell short. The designers themselves hadn’t felt the thing yet either.

That’s the asymmetry coding agents collapse. The loop between “I have an inkling” and “I am tinkering with a working version of the inkling” has finally closed for non-developers. They still can’t and mostly shouldn’t ship production code, but they don’t need to. The prototype is enough to do the design work. Once the gatekeeping melts, the next question is institutional: where does the next generation of interface inventors come from? Matuschak’s answer:

So, what now? We’ve spent decades building HCI programs that mostly look like computer science departments with design electives. But if we’re moving toward a world where invention is bottlenecked more on imagination than on technical expertise, we may have that backwards. We may need programs that look a little more like art school with technical electives—learning to develop ideas from intuition before being able to express them precisely, to discover by playing with the material.

Title slide and content page from Andy Matuschak's MIT HCI Seminar talk "Apps and programming: two accidental tyrannies" dated 2026-03-03, showing a table of contents and lecture notes.

Apps and programming: two accidental tyrannies

On coding agents, malleable software, and the future of interface invention

andymatuschak.org iconandymatuschak.org

Humans are the bread in the sandwich, and the AI is in the middle.

That’s Dan Shipper on his podcast AI & I, talking with Every’s Kieran Klaassen, the engineer behind the compound engineering plugin. They’re working out where humans actually belong in an AI-driven workflow. It’s the same split showing up on the design side.

Klaassen, on the polish step at the end of the work:

The other moment comes at the end. Something comes out. How do you validate it? Well, it’s already tested—browser automated testing has clicked through everything, all the requirements are clearly specified, and it says everything works. But the beauty comes in when a human looks at it, clicks around, and has a feel for it: “Oh, this doesn’t feel right. We can polish it. We can make it better. There’s something still missing. We can make the design better.” […] all the way at the end, when everything is done, you can elevate everything and make it even better. And I think we need to do that, because if we don’t, it will all be slop—all the same. It’s very important to make it feel great because the bar is high, and the bar will always get higher.

“It will all be slop” is the line every team should have taped to a monitor. A passing test suite and a green PR don’t tell you whether the thing is actually any good. That judgment still lives with a human at the end of the workflow. Klaassen is correct that the bar keeps moving up, not down, and the teams who treat the polish step as optional are the ones whose products will look interchangeable in twelve months.

Klaassen, on the art-and-ownership argument:

But I do think that in the end, if you ship something—if you make a statement in the world—and you want it to be your own, you have to say yes or no at some point. You cannot fully automate everything. It’s a bit like making art. If you want it to be yours, it needs to come from you or somehow be connected. So I believe having those moments where you decide—where you choose what you enjoy—is so important. That’s why it’s so important to do things you enjoy and love.

Whatever your version of beautiful is, that’s the bread. Everything else is filling.

Cover art for "AI & I" podcast by Every, featuring a smiling man with glasses rendered in gold tones against a purple background.

The AI Sandwich: Where Humans Excel in an AI World

‘AI & I’ with compound engineering creator Kieran Klaassen

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Karri Saarinen, Linear’s co-founder, calls out the confusion that most of the new design tooling is built on top of:

Design keeps being misunderstood in our industry. New tools keep promising to generate interfaces faster, move words to product instantly, or collapse design directly into code. The assumption behind them is clear: that design is the act of producing. That is the misunderstanding. The hard part of design is rarely generating the form. It is understanding the problem well enough to know what and how something should exist at all.

What I appreciate about Saarinen’s argument is that he doesn’t stop at the diagnosis. He reaches for Christopher Alexander’s Notes on the Synthesis of Form and recovers a vocabulary term the industry has been missing:

Christopher Alexander came closer than anyone to naming this clearly. In Notes on the Synthesis of Form, he describes design as the search for a good fit between a form and its context. Context, in his sense, is not a background condition. It is the full set of forces that make a problem what it is: human needs, technical constraints, conflicting requirements, habits, edge cases, and relationships that are easy to miss until you spend time with them. Bad design appears where those forces remain unresolved. Good design appears where those misfits have been worked through carefully.

Context as forces, not background. The current generation of prompt-to-code tools, including Lovable, Figma Make, and Claude Design, is very good at producing a plausible form against a thin slice of context. Saarinen describes the symptom directly:

You can already see the result in products that look polished, ambitious, and impressive at first glance, but begin to unravel the moment you actually use them. They feel brittle, poorly integrated, and full of decisions that were never fully worked through. The form is there. The fit is not.

That same bottleneck shows up on the workflow side: production speeds up, judgment doesn’t.

Saarinen’s closer:

The risk is mistaking generated form for solved problems.

That is the mistake to watch for, in your own work and on your team. Design is what happens when someone takes the time to understand the forces and works the misfits out of the form.

Loose, expressive ink and wash sketch of an abstract architectural structure with dense crosshatching and gestural line work.

Output isn’t design

Design keeps being misunderstood in our industry. New tools keep promising to generate interfaces faster, move words to product instantly, or collapse design directly into code. The assumption behind them is clear: that design is the act of producing.

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I’ve been pro-prototype: PMs replacing PRDs, designers prototyping interactions in code. Pavel Samsonov, writing at Product Picnic, aims at exactly that position. He opens by borrowing a distinction from Andy Polaine:

Demos and prototypes sit on a continuum, but I consider demos something to help you show a concept to other people in a form that looks and feels like the real thing. Prototypes are things you create to test something you don’t know until you build and test it.

Correct distinction. A demo succeeds on stakeholder approval; a prototype succeeds on learning. Both artifacts can be interactive and polished. What separates them is what counts as success. Samsonov on what happens when teams conflate them:

The only thing these demos are helping you test is whether your stakeholder likes what they see (the first loop) and as soon as they say “yes,” it becomes good enough to ship. Whether that second loop (releases go out, measurements come in) ever gets tracked or not is not something I’d be willing to put money on. Because once the demo is productionized, it goes from the realm of delivery velocity (which gets you shoutouts and promotions) into the realm of maintenance (which tends to be ignored even as it eats up more than half of the team’s bandwidth).

AI makes it easier to produce both, and Samsonov’s read on what happens when teams use the speedup wrong:

Shoving out more prototypes is not a heuristic for success; it is a heuristic for failure because it shows that you don’t know what you are trying to learn.

Agreed. Samsonov goes further:

This is exactly why AI-generated prototypes are not working, and have not helped anyone do anything ever. Some have accused me of going too far with this assertion, but I stand by it, because it is rooted in the very nature of what a prototype is (and is not), and what makes it successful (or does not).

Here’s where I differ. Brian Lovin’s Notion prototype playground exists because static mocks enforce golden-path thinking. The playground surfaces the messy middle of AI chat: follow-ups and latency changes no one mocks up. Édouard Wautier’s Dust team prototypes state changes and motion Figma can’t show. Figma PMs ran five user interviews in two days off an AI-built prototype, which is a textbook closed second loop. All three count as prototype work.

Samsonov’s diagnosis is right. His absolute stance is, well, too absolute. AI-generated prototypes haven’t helped anyone only if you assume they’re all demos, which is exactly what the distinction he just drew tells us not to assume.

Product Picnic 64 title card over a vintage black-and-white photo of three people eating and drinking outdoors on rocky terrain.

Designers will never have influence without understanding how organizations learn

We confuse prototypes with demos, and validation with confirmation bias. As a result, we cannot lead — instead, we are led.

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In my previous item, I linked to a post by Adi Leviim who made the case against chat as the AI interface default, reading the 2024 wave of GUI retrofits AI labs shipped—Canvas, Artifacts, Projects, Computer Use, Deep Research—as the industry admitting a text box alone wasn’t enough. Matt Webb, writing on Interconnected, wants every service to ship a CLI instead. Both arguments are about text. They look like they contradict. They don’t. Webb’s case for going headless:

It’s pretty clear that apps and services are all going to have to go headless: that is, they will have to provide access and tools for personal AI agents without any of the visual UI that us humans use today. […] Why? Because using personal AIs is a better experience for users than using services directly (honestly); and headless services are quicker and more dependable for the personal AIs than having them click round a GUI with a bot-controlled mouse.

Webb’s CLI sits on the agent-to-service layer. Leviim’s retrofits sit on the human-to-agent layer. The text on one side is a protocol for machines. The text on the other is a user writing out intent in sentences. Both are text, but the role is different. Webb makes the split explicit when he turns to what it means for design:

So from a usability perspective I see front-end as somewhat sacrificial. AI agents will drive straight through it; users will encounter it only once or twice; it will be customised or personalised; all that work on optimising user journeys doesn’t matter any more. But from a vibe perspective, services are not fungible. […] Understanding that a service is for you is 50% an unconscious process - we call it brand - and I look forward to front-end design for apps and services optimising for brand rather than ease of use.

Interesting, right? Webb believes that the need for human-facing UI and therefore user journeys will be less. He’s designing for an agent-first world.

Webb, goes on…

If I were a bank, I would be releasing a hardened CLI tool like yesterday. There is so much to figure out: […] How does adjacency work? My bank gives me a current account in exchange for putting a “hey, get a loan!” button on the app home screen. How do you make offers to an agent?

The agent becomes the surface designers have to figure out.

Abstract illustration of tangled white curved lines forming loose oval shapes against a soft green background with muted circular shadows.

Headless everything for personal AI

It’s pretty clear that apps and services are all going to have to go *headless:* that is, they will have to provide access and tools for personal AI agents without any of the visual UI that us humans use today.

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Every major AI lab spent 2024 bolting GUI surfaces onto chat: Canvas, Artifacts, Projects, Computer Use, Deep Research. That’s seven retrofits across three AI firms in twelve months. Adi Leviim, writing for UX Collective, reads that wave as the industry conceding in public what designers have been saying since Amelia Wattenberger’s 2023 essay on why chatbots aren’t the future of interfaces. His setup for why the default took hold:

Open any AI product launched in the last three years. Ignore the model, the logo, the branding. You will find the same interface: a text input at the bottom of the screen, a send button, and a scrollback of alternating messages. This is not a random convergence. It is the interface that fell out of what large language models could do on day one: pattern-match on text. In 2022 we had a new capability and no time to design around it, so we shipped what was fastest to build and called it conversational AI. Three years later, the fastest thing to build has become the thing everyone builds. That is how defaults calcify.

The lag between Wattenberger’s essay and the retrofit wave was three years. Leviim counts the retrofits as evidence the rectangle was always going to need help:

Calling this progress is charitable. It is the industry discovering, retrofit by retrofit, that a text box alone cannot hold a meaningful creative surface. You cannot edit a thousand-line document by asking the bot to re-output it with “line 312 changed to X”. You cannot iterate on a design by describing it. You cannot plan a research project without seeing the plan. The moment the task has a structured output, the chat box becomes the wrong place to work, and the vendors put a canvas, a side panel, an editor, a workspace, or a planner next to it.

“Retrofit by retrofit” is the phrase that carries his argument. Each retrofit is a clickable, scrollable, draggable pattern the chat box had removed. The AI labs are rebuilding what 2015-era UI already had.

Leviim continues, separating intent from chat:

Expressing intent does not require prose. A date picker expresses temporal intent more precisely than any sentence. A pair of sliders expresses a tradeoff more legibly than a paragraph. A file upload expresses “work on this thing” without ambiguity. Every one of these is intent-based. None of them is chat. The chat box is one possible implementation of the paradigm, and by all accessible evidence it is a low-resolution one.

Jakob Nielsen’s 2023 essay, “AI: First New UI Paradigm in 60 Years,” treated chat as the way to express intent. Leviim agrees intent-based interaction is the shift. He argues chat is the wrong way to express it. Date pickers, sliders, file uploads are all intent surfaces, and none of them is chat. Which is where the design work goes next:

the good AI UX work of the next three years will be distributed across a thousand of those scoped surfaces rather than concentrated in one generalized text field.

That’s the brief for anyone designing AI products.

Side-by-side comparison of a Structured UI with a dropdown, date picker, checkboxes, and range slider versus a minimal AI Chat Interface with a text input and Send button.

The chat box isn’t a UI paradigm. It’s what shipped.

Before LLMs we had direct manipulation, structured forms, and progressive disclosure. Then we collapsed all of it into a text box.

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Showing stakeholders prototypes is often a high-wire act. Back in the old days, that’s why we showed wireframes prior to high-fidelity comps, or mockups. But now with tools like Lovable or even Claude Design, where the prototype demos really well, it’s easy to mistake it for a product that is shippable. The stakeholder in the room could easily say “ship it.”

That used to be where the Figma-to-code handoff became visible. Now it’s invisible. Greg Kozakiewicz, writing on LinkedIn, wants designers to see it again. He updates an old construction-industry line for the AI era:

We used to confuse the drawing with the building. Now we confuse the prototype with the product. A working prototype also accepts everything. It will let you register, log in, fill out a form, submit something. It all works. In the demo. On a good laptop. With a fast connection. With someone who knows what they’re doing and what the app is supposed to do.

The design-to-code gap didn’t vanish when AI made prototypes interactive. It went underground. Now it shows up as a stakeholder saying “looks great, let’s ship it” to something that couldn’t survive real data or production constraints. Kozakiewicz puts a number on it:

AI gets you to about 60%. A solid, reasonable, generic 60%. The layout makes sense. The flow is logical. The copy is clear enough. It looks like a product that works. And for a lot of people, especially people making decisions about budgets and timelines, 60% looks like 90%. Because the last time they saw a prototype, it was a static Figma file with “Lorem ipsum” everywhere.

A hand lifts a modular glass block from a detailed architectural scale model, revealing illuminated interior floors with tiny figurines inside.

Paper accepts everything. So does a prototype.

There’s an old saying in construction. Paper will accept everything. You can draw anything on paper. A swimming pool on the roof. A spiral staircase made of glass. A cantilever that defies physics. Paper doesn’t argue. Paper doesn’t say “this won’t hold.” Paper just sits there, looking beautiful, full of promise.

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The designer’s role is widening at both ends of the product stack. Earlier, I linked to a post by Chad Johnson arguing designers gain influence by moving upstream: becoming orientation devices for the team, shaping the problem before it gets named. Daniel Mitev, writing for UX Collective, argues designers gain authorship by moving downstream, into the code:

The industry has been asking whether designers should code for over a decade. It was always the wrong question, or at least the wrong framing. It implied the barrier was technical: that designers lacked something fundamental, something that required years of study to acquire. Learn TypeScript. Understand the DOM. Earn your way across the divide. That wasn’t the barrier.

Mitev’s argument comes down to access. AI tooling compresses the translation layer and returns authorship to the designer:

What AI tooling gives back is authorship over the surface layer — the part users actually touch. A designer can now open the codebase, adjust how an element behaves, change how a transition feels, and verify the output against their own intent in real time. The easing curve gets set by the person who decided what it should feel like. The hover state gets defined by the person who thought through why it matters. That work no longer requires an interpreter.

He points at Alan’s “Everyone Can Build” initiative—283 pull requests shipped by non-engineers over two quarters, each merged after engineering review—as evidence it’s already happening.

Johnson and Mitev aren’t in conflict. They’re describing the same shift from opposite ends. The interpreters at the top of the product stack—PMs who owned problem framing and prioritization—are compressing. The interpreters at the bottom—frontend engineers translating intent into code—are compressing too. Both jobs return to the designer who understood the intent first.

The role widens. Some designers will gravitate to one end or the other. The designers who stretch the full range—orientation work and authorship—are working the widest version of the job.

A hand pressing an Enter key above a terminal showing a git commit command, with text reading "Designers finally have a say in the product they design.

Designers finally have a say in the product they design

AI didn’t teach designers to code. It gave them back the decisions that were always theirs.

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(Second link to Chad Johnson this week, but I just discovered his Substack, so ¯\_(ツ)_/¯.)

Chad Johnson, writing in his newsletter, argues that designer influence in product decisions comes from something other than craft output. He lays out the underlying dynamic:

Roadmaps are shaped less by who has the best ideas and more by who controls the framing of tradeoffs. Every roadmap decision is a bet: build this instead of that, now instead of later, for these users instead of those. Whoever makes the risk feel smaller tends to win.

So where does the designer fit? Johnson:

The most influential designers at startups do not position themselves as makers of screens. They act as orientation devices for the team. Orientation is the ability to help a group understand where they are, what matters, and what tradeoffs are real. It precedes prioritization, and it makes decision-making possible.

A designer whose output stops at screens is working on the wrong layer of the problem. Johnson lists the skills that back the orientation role:

Designers who shape direction invest in strategic framing, business literacy, and narrative construction. They learn to say no with evidence and to disagree without drama.

Johnson’s list is right as far as it goes. He understates one skill: legibility. A lot of design influence breaks down at translation. The thinking is strategic; the communication stays in design vocabulary. A sharp problem statement understandable only to other designers stays in the design review. Designers who change the conversation make their analysis readable in product and business terms without flattening it. That’s the same move Johnson gestures at when he describes “decision-ready artifacts” as “tools for comparison… designed to provoke judgment, not admiration.”

Johnson’s closer calls the future of design leadership “quieter, more rigorous, and deeply strategic.” That’s right. It’s also a role that depends on being read by the people making the call.

Large-scale flowchart on a white wall with quirky decision questions including "Have you ever missed an airplane flight?" and "Are you good with names?

Why Most Designers Will Never Influence Product Roadmaps

A practical explanation of how roadmap decisions are really made, and how designers can gain influence

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Two podcast conversations with frontier-lab design leaders on what designing at an AI lab looks like day-to-day. I previously linked to Lenny Rachitsky’s interview with Jenny Wen, head of design for Claude, where she described a redistribution of designer hours: less mocking, more pairing with engineers, a sliver of direct implementation. The activities themselves still look like design.

Ian Silber, head of product design at OpenAI, on Michael Riddering’s Dive Club, describes work that doesn’t fit the same list:

Designers working on this are hopefully spending a lot less time in Figma or whatever tool you use to draw pixels, and more time really thinking about how you interact with this thing, and the fact that the model really is the core product.

Silber’s concrete example is onboarding. Instead of building a first-run tutorial, his team shapes what the model already knows about the person:

We have this super intelligent model that could probably do a much better job trying to understand what this person’s goals are […] We’re really stripping back a lot of what you might traditionally do and trying to say, “Well, actually […] let’s think about like how we should give this context to the model that this person is brand new and they might need some handholding.”

The traditional response adds UI around the problem. Silber’s team takes it out and gives the model enough context to meet the user where they are.

That kind of work needs its own scaffolding, and OpenAI is building it:

We have a whole system called the Dynamic User Interface Library, which allows us to design things that the model can then interpret.

Primitives the model composes at runtime, shaped by system prompts and context rather than drawn flow by flow. Wen is describing a redistribution of designer hours inside activities that still look recognizable. Silber is describing activities that don’t quite have names yet. And yes, that is still design.

Ian Silber - What it’s like designing at OpenAI

If you’re like me you gotta be curious... what’s it like designing at OpenAI?

youtube.com iconyoutube.com

The gap between an AI-produced prototype and a shippable product has a shape. Most of us assume it’s the visual 20%: the polish AI output drifts on. Chad Johnson’s case is that the 20% is the trivial part, and the real gap sits upstream of everything visible.

Chad Johnson, writing in his newsletter:

The deeper issue was that nobody had asked whether a prototype was even the right artifact to produce at that stage. The PM had made three assumptions about user intent that we hadn’t validated. They’d skipped past a critical question about whether this flow needed to exist at all, or whether the real problem was upstream in the information architecture. They’d built a beautiful answer to a question nobody had confirmed was worth asking. That’s the part that stuck with me. Not the visual gaps. The thinking gaps.

That lines up with what I’ve been calling C+ out of the box: artifacts that read well and seem credible until you apply critical thinking. Johnson gets specific about what’s actually missing, and none of it is visual: the assumption nobody validated, the upstream question nobody asked. The interface was fine. The thinking was absent from the (probably) AI-generated PRD.

Johnson again:

…design production got democratized, but design judgment didn’t. Anyone can make something now. Almost nobody new learned how to think well about what should be made, why, and for whom. And that gap, between what’s possible to produce and what’s actually been thought through, is now the entire playing field for our profession. Designers aren’t becoming obsolete. They’re becoming stewards.

Judgment still takes years to build, and no tool compresses that.

The last 20% is rarely the gap that matters. The first question—should we build this?—almost always is. Very few teams have the muscle to ask it.

Abstract digital art featuring curved, layered surfaces with fine parallel lines in warm orange, red, and deep blue gradients.

The Last 20% and Who’s Asking Why?

Everyone can build now. Almost nobody stops to ask if they should.

chadsnewsletter.substack.com iconchadsnewsletter.substack.com

Tara Tan surveyed more than a dozen AI design tools for The Review. Her field audit sits alongside the design-process compression argument:

In working with these tools, one insight emerged for me: the tools that understand your design system produce better output than the ones that don’t. […] The competitive moat in this market is not generative quality, which is commoditizing fast. The moat is the design system graph: the tokens, components, spacing scales, typography rules, and conventions that make your product look like your product and not a generic template. Whoever makes that system machine-readable for agents will win the enterprise.

That’s the operational reason my proposal for an agent design team hinges on a rock-solid design system. What distinguishes output across the tools Tan surveyed is whether the generator respects your existing design system or treats every request as a fresh mood board.

Tan’s other finding is the role-shift:

The same shift is happening in design. At Uber, Ian Guisard didn’t stop being a design systems lead when uSpec automated his spec-writing. His job shifted from producing documentation to encoding expertise, writing agent skills, defining validation rules, deciding what “correct” means for each component across seven platforms. The human became the system designer, not the system operator. […] The canary is singing. And the song is about the work shifting from execution to judgment, from operating the system to designing the system itself.

Same title, different job. Ian Guisard’s taste still matters; it lives in the skills and validation rules now, not the deliverables. That’s “follow the skill, not the role” made concrete. Guisard used to write specs; now he writes the rules the system follows to validate them.

The infrastructure is catching up to the process. Tan’s implicit prescription is straightforward: make the design system machine-readable, win the enterprise. Some of that tooling is already out in the open. Southleft’s Figma Console MCP (which Uber’s uSpec is built on) lets agents operate on tokens and components without a custom platform.

But tooling alone isn’t enough. Most of us aren’t Uber. The path for teams without a dedicated design systems lead still needs someone to do the work Guisard did: encoding the expertise and defining what “correct” looks like across platforms. That’s where the next round of tooling needs to land.

The Design Agent Landscape" diagram categorizing AI design tools into three groups: Agent-first canvas (Pencil, Paper, OpenPencil), Design system-first (Figma MCP, Console MCP, Google Stitch), and Code-native (Subframe, MagicPath, Tempo, Polymet, Magic Patterns, Lovable, Bolt, v0, Replit).

The Design-Build Loop

Design is where AI product workflows meet their hardest test: an audience that will always, primarily, be human. A look at the tools, teams, and infrastructure emerging around AI design agents.

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A sleek high-speed bullet train with glowing headlights crossing a bridge through dense fog over a misty landscape.

Acceleration Is Not Automation

I’ve been wandering the wilderness to understand where the software design profession is going. Via this blog and my newsletter, I’ve been exploring the possibilities by reading, commenting, and writing. Many other designers are in the same boat, with Erika Flowers’s Zero Vector design methodology being the most defined. Kudos to her for being one of the first—if not the first—to plant the flag.

Directionally Flowers is right. But for me, working in a team and on B2B software, it feels too simplistic and ignores the realities of working with customers and counterparts in product management and engineering. (That’s her whole point: one person to do it all, no handoff.)

The destination is within view. But it’s hazy and distant. The path to get there is unclear, like driving through soupy fog when your headlights reflecting off the mist are all you can see.

Every few weeks, another essay or YouTube video announces that AI has killed craft. One of my favorite designers writing about design, Christopher Butler, goes the other way:

No knowledge I possess about design—the incorporeal understanding that makes what I create better than an off-the-shelf template or something done by someone without my experience—is made irrelevant by AI. Nor is it contradicted by my use of AI tools. Structure still communicates before content. Visual hierarchy still guides attention. Negative space still creates rhythm. These principles don’t vanish because I’m working through AI rather than directly manipulating pixels. The craft migrates to a different level of abstraction. But it remains craft.

Butler’s claim is that the principles don’t vanish; they operate at a higher altitude. The unfinished part is naming where that altitude actually is. For product designers, it’s concept and hierarchy: the decisions that require knowing the user and the stake someone is willing to carry. The generated layout and the choice of components are still outputs. What’s left of design is the judgment that picks between them.

Butler’s sharper line is the binary between consumption and practice:

Someone who generates an interface with AI and calls it done isn’t practicing craft. They’re consuming convenience. Someone who generates an interface, inspects it, questions what it’s actually communicating, refines the structure, generates again, compares variations, understands why one serves the user better than another—they’re practicing craft. They’re building knowledge through iteration. The tool doesn’t determine whether you’re working with craft. Your approach does.

That’s Jiro Ono’s shokunin applied to interfaces: craft as lifelong practice, not manual labor. A camera doesn’t take a picture, and a model doesn’t make a design. That decision is the craft.

Butler’s argument reassures me. What worries me is how optional that decision is becoming. The output already looks finished. The designers who keep asking why one version serves the user better than another will still be designers in five years. The rest may still have jobs, as operators of a tool doing the work their taste used to do.

Close-up of a vibrant fingerprint with swirling ridge patterns in orange, red, blue, and yellow iridescent colors with glittery highlights.

Craft is Untouchable

I have a vested interest in the title of this piece being true. I’ve spent decades developing craft—not just making things, but understanding systems, seeing patterns, making judgments that can’t be reduced to prompts. If AI eliminates the need for that expertise, I’m in trouble.

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Tommaso Nervegna writes about LinkedIn killing its Associate Product Manager program and replacing it with a new role called the “Full Stack Builder.” The structural bet is interesting, but the finding from their rollout is what matters:

The expectation was that AI would be a great equalizer: juniors would benefit most because AI would close their skill gaps, while seniors would resist the change. The reality was the opposite. Top performers adopted AI fastest and derived the most value from it. Why? Because they had the judgment and experience to know what to ask for, how to evaluate the output, and where to apply it for maximum leverage.

That tracks with everything I’ve predicted, experienced, and seen. The skill that makes AI useful is knowing what good looks like before and after the model generates something. That ability comes from reps.

Nervegna distills LinkedIn CPO Tomer Cohen’s thesis to five skills AI cannot automate:

The five skills that AI cannot automate, according to Cohen, are Vision, Empathy, Communication, Creativity, and Judgment. As he puts it: “I’m working hard to automate everything else.”

The operational version:

The critical insight: the builder orchestrates the agents. The agents execute. Judgment stays human. This is not about replacing people with AI. It’s about compressing the team needed to ship something meaningful from fifteen people to three - or even one.

I’ve been calling this the orchestrator gap: the distance between a designer who uses AI and one who directs it. LinkedIn just gave it a job title. I think we will see more companies go this way. Whether or not it’s a good idea remains to be seen.

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The Full Stack Builder: The End of the Design Process as We Know It

The double diamond is a liability. Engineers ship faster than designers can explore. The PM role is dissolving and the three profiles that will survive this era look nothing like who we’ve been hiring

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I’ve watched design team values die in a Confluence page. The offsite happens, the Post-Its get transcribed, the principles get written up with care, and then everyone goes back to their desks and ships exactly the way they did before. I’ve seen it with product principles and brand values too. The deck gets built, implementation starts, and the deck gets forgotten.

Vitaly Friedman, writing for Smashing Magazine, on why this matters more than ever:

We often see design principles as rigid guidelines that dictate design decisions. But actually, they are an incredible tool to rally the team around a shared purpose and document the values and beliefs that an organization embodies. They align teams and inform decision-making. They also keep us afloat amidst all the hype, big assumptions, desire for faster delivery, and AI workslop.

Friedman again:

In times when we can generate any passable design and code within minutes, we need to decide better what’s worth designing and building — and what values we want our products to embody. It’s similar to voice and tone. You might not design it intentionally, but then end users will define it for you. And so, without principles, many company initiatives are random, sporadic, ad-hoc — and feel vague, inconsistent, or simply dull to the outside world.

You might not write principles intentionally, but your product will have them anyway. The question is whether you chose them or inherited them by default.

Friedman closes with the part most teams skip:

Creating principles is only a small portion of the work; most work is about effectively sharing and embedding them. It’s difficult to get anywhere without finding ways to make design principles a default — by revisiting settings, templates, naming conventions, and output. Principles help avoid endless discussions that often stem from personal preferences or taste. But design should not be a matter of taste; it must be guided by our goals and values.

Creating principles feels productive. But alignment without embedding is a Confluence page nobody opens twice. Principles have to show up in the Figma component library, the ticket template, the review rubric. They have to be repeated so that they are ingrained. They have to become the path of least resistance.

Smashing Magazine article title card: "A Practical Guide To Design Principles" by Vitaly Friedman, tagged Design, UX, UI.

A Practical Guide To Design Principles — Smashing Magazine

Design principles with references, examples, and methods for quick look-up. Brought to you by Design Patterns For AI Interfaces, **friendly video courses on UX** and design patterns by Vitaly.

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Dan Saffer applies mid-century existentialism to the question of what “meaning” actually requires of the people building digital products, and the result is unusually rigorous. His sharpest move is applying Sartre’s concept of “projects” to AI tools:

When someone uses ChatGPT to write an essay, the Sartrean question is: whose project is this really? If the user is exploring ideas and using the tool as a thinking partner, they’re taking it up into their own meaning-making project. But if they’re pasting in a prompt and submitting the output unchanged, the system has effectively become the meaning-maker, and the user has become a delivery mechanism. The same tool can function either way. The design question is which relationship the system encourages.

Saffer connects this to Camus and the problem of frictionless design:

When every friction is removed in the name of efficiency, the activity can be hollowed out. There is nothing left to push against, and meaning drains away. This is something that AI systems have become exceedingly good at. Push the sparkle button, the task is done for you, and you have learned nothing and enjoyed nothing.

The HCI/UX field spent decades optimizing for friction removal. Saffer’s argument is that some friction is where the meaning lives. Design the struggle away and you don’t help the user. You empty the experience. Not every friction should be removed.

Saffer’s closing:

This sensibility insists that users are not information processors, not customers, not eyeballs, not tapping fingers, and not data sources. They are meaning-making beings whose freedom and dignity are at stake in every interaction. It asks designers to take seriously the existential weight of what they build. The systems we design become part of the conditions of human existence, shaping what people can choose, what they can see, who they can become.

Saffer covers Sartre, Camus, Kierkegaard, Heidegger, and de Beauvoir in the full piece, each applied to contemporary design problems. It’s a lot, and it’s all good.

Collage of five black-and-white portrait photos of mid-20th century philosophers, including one woman and four men, one holding a pipe.

The Existential Designer: Facilitating Meaning Through Interaction

Designers like to talk about making meaningful products or using the tools of design to make meaning.

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Yours truly got quoted in Fast Company. Grace Snelling, surveying the industry reaction to Lenny Rachitsky’s TrueUp hiring data, pulled a comment I left under Rachitsky’s original Twitter post:

Designers have designed themselves out of the equation because of design systems. But, IMHO, the secret sauce has never been the UI. It was the workflows and looking across the experience holistically.

Let me expand on that. The UI has always been the easiest part of product design. Design systems made that even more true. What separates a great product from a mediocre one is understanding our users deeply enough to create experiences that actually delight them. That understanding is the work AI can’t do, and it’s the work too many teams were already skipping before any standoff started.

The data behind the standoff: Rachitsky’s analysis of TrueUp’s job market tracker shows design roles have been flat since early 2023 while PM and engineering roles surged. (Quick side note: this data is for tech startups, not the general tech industry or design industry at large.) His theory:

I don’t know exactly what’s going on here, but it does feel AI-related. […] Unlike PM and eng, which started growing in 2024 (two years post-ChatGPT), design didn’t. If I had to venture a theory, I’d say that because AI is allowing engineers to move so quickly, there’s less opportunity—and less desire—to involve the traditional design process.

Claire Vo, founder of ChatPRD, puts the harder version of why:

Often design teams & designers are the most resistant to change org in the EPD triad, with highly vocal AI opponents, and little skill or interest in the art of campaigning for influence or resources. […] If a PM or engineer can get 85% there with tailwind and a dream, you better come to the table with more than ‘I represent the user.’

“I represent the user” was never enough on its own. It just went unchallenged when designers were the only ones who could ship polished interfaces.

Anthropic’s chief design officer Joel Lewenstein on where the EPD triad actually lands:

I think there’s a lot of role collapse at the very beginning, but there are still pretty clear swim lanes as things get into the later stages of product development. […] It’s like a Venn diagram that’s coming closer together.

Three hands pointing toward a central point on a red background, surrounded by colorful lightning bolt shapes in green, blue, and pink.

Why are designers, engineers, and product managers in a ‘three-way standoff’?

New data has the design community in a debate about the future of their jobs.

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Nate Parrott, a product designer at Anthropic, in an interview with Ryan Mather for AI Design Field Guide:

More Google Docs than you’d think. More Slack posts than you’d think. I meant what I said earlier: I think that this is the era of designers who design with words more so than designing with pixels.

Parrott describes a content design team whose job is making alien concepts legible:

We have several people at the company on the design team whose job is content design. Their job is basically to look at concepts which are very alien, and figure out how to make them legible to human beings. They don’t draw any pixels, but their work is really important because they are literally thinking about the words we use to describe and the mental models we expect people to put on that will make this stuff work.

The Figma work, Parrott says, is “the easy part.” He uses Anthropic’s design system, drops in components, and moves on. The hard work is upstream: expressing the ideas, figuring out the right language, talking to users. The production of screens has become the smallest slice of the job.

Jenny Wen described designers at Anthropic shipping code, prototyping against the live model, stretching into PM territory. Parrott is describing the same shift from a different angle. The deliverable used to be the mockup. Now the deliverable is the thinking that precedes it.

Vibrant abstract illustration of stylized flowers with glowing, blurred edges in bold red, yellow, orange, pink, and blue tones against a soft gradient background.

AI Design Field Guide

Learn techniques from the designers behind OpenAI, Anthropic, Figma, Notion & more

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The first time I wrote about Jenny Wen, I pushed back. She said the design process was dead, and I argued the proportions had shifted but the process itself was intact. I also noted a context problem: her “ship fast, iterate publicly” approach makes sense for greenfield AI products at Anthropic but gets harder with established install bases.

Wen has been making the rounds and in a new interview, I’m finding a lot that I’m nodding my head to.

Jenny Wen, speaking on Tommy Geoco’s State of Play:

Often design needs to follow what the model is capable of and design from there, as opposed to starting from a design vision first. I think that can feel tough as a designer because you’re like, oh, I want to be design-led, we should be designing it first and then the technology should follow. But I think that’s just the reality of working at a research lab where the technology is emergent and you have to sort of decide what to do with it.

“Design follows the model” is an interesting phrase from a design leader. It inverts the dogma that design should lead and engineering should follow. But Wen isn’t being defeatist. She’s describing a practical reality at at a leading AI lab where the models’ capabilities are changing faster than any roadmap can account for.

This shows up concretely in how her team works:

The big thing is designers are implementing code, through using Claude Code. That has been the biggest difference from working at Anthropic versus back when I worked at Figma. […] Even today, we were reporting some bugs and some quality issues, and one of the designers was like, “Cool, let me just fix them.” And that was cool to just not have to tag an engineer for them to do anything.

A designer casually fixing production bugs without tagging an engineer. Just another Tuesday at Anthropic.

Geoco’s summary of Wen’s argument crystallizes something we’ve all been thinking quietly about:

She said, having taste versus being able to execute are two completely different things. They’re usually bundled together, but they don’t have to be. And in a world where AI can increasingly execute, the question becomes, and it’s kind of uncomfortable, do you actually have good taste or are you just pushing pixels around?

That’s the thread tying all of this together. When designers are closer to the product, fixing bugs in production, prototyping against the live model, the judgment they’re applying isn’t visual. It’s product sense: knowing which of those 12 options is worth shipping, which edge case will break trust, when the model’s output is good enough for real users. That’s the taste Wen is describing, and it has very little to do with pixels.

A lot of designers have been coasting on execution skills that felt like taste. They debate corner radii and centering labels in a button with amateur vs pro designer memes. Who cares! AI is about to make the difference visible.

The New Era of UX Designers

Jenny Wen led design on FigJam, one of the most playful tools to hit design in a decade. Now she’s at Anthropic designing Claude. Not just the model, but the product that millions use daily.

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Stripe design manager Kris Puckett, speaking on Michael Riddering’s Dive Club, spent the first half of the conversation demoing metal shaders, custom ocean animations, and a full iOS reading app he built with Claude Code. Then he stopped himself:

AI native has to be beyond just “I made a really cool shader” or “I made this dither effect that every other person is making.” I was doing that today and then I was like, “Oh my gosh, this is… why am I doing this? There’s a hundred of these that are way better than what I’m making right now.”

So what does AI-native design actually look like? Puckett’s answer is “soul”—the quality that makes work feel specifically, unmistakably yours:

I think what people are going to be desperate for is more of that human side of things. They’re going to be longing for […] an era they’ve never experienced because they’re younger, that MySpace generation where your MySpace page was deeply personal to you. My MySpace page was complete custom Kris Puckett perfection at that time. And I think that we’re going to want to see that come back. And I think people are going to want more of those—your portfolio looks and feels like you.

“Soul” is doing a lot of work as a concept there. What Puckett is describing sounds a lot like taste—the ability to make something that feels intentional and specific rather than procedurally generated. His workflow backs that up. Being contrarian, he explicitly rejects the “let the agent run” approach:

I want off that cycle. I do not want to be riding that bike race with anyone else because that’s not how I view these things. They are a force multiplier, but I want them to be focused. I want it to be something that I feel is still authentically me.

What unlocked all of this for Puckett wasn’t technical skill—he’s a designer, not an engineer. It was admitting “I don’t know” and starting anyway. He’d been dreaming of building his own software for 20 years. Claude Code’s blinking cursor was enough to get him started.

Kris Puckett - Becoming an AI-native designer

Today’s episode is with Kris Puckett (https://x.com/krispuckett) who has led design at Mercury, Dropbox, and now as a design manager at Stripe. His journey is the perfect example of what it looks like to lean into this moment in time with AI.

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Figma is opening its canvas as a writeable surface for AI agents. Matt Colyer, product director at Figma, on why this matters:

Design decisions—from color palettes and button padding, to typography and interactivity—have always defined how products take shape. No matter how small, those decisions add up. They make your product and user experience stand out from the rest. To date, AI agents haven’t had this context, which is why so many designs created by AI often feel unfamiliar and generic.

The fix is beefing up skills files, by encoding a team’s design decisions, conventions, and sequencing rules. Agents read them before they touch the canvas. The use_figma tool lets Claude Code, Codex, and other MCP clients create and update assets tied to your design system. Colyer on what that changes:

Your conventions are no longer static documentation. They become rules agents follow as they work—applied through components, variables, and the structure you’ve already defined.

The detail worth paying attention to is what Colyer describes as a self-healing loop. When an agent generates a screen, it screenshots the result, checks it against the design system, and iterates. Because it’s working with real components and auto layout, those corrections compound through the system itself, not just the pixels on screen.

It’s free during beta, with plans to move to a paid API. Figma is finally joining the party as Subframe, Paper, and Pencil all offer this workflow already.

Terminal window titled "earthling — zsh" showing an AI prompt to build a component set from a button.tsx file, with output confirming 72 button variants created, overlaid on a Figma canvas with UI components.

Agents, Meet the Figma Canvas

Starting today, you can use AI agents to design directly on the Figma canvas. And with skills, you can guide agents with context about your team’s decisions and intent.

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Gui Seiz designs at Figma. His team uses Claude Code to bridge design and code. And he still reaches for the canvas when precision matters.

Seiz, speaking on Claire Vo’s How I AI podcast:

I don’t think we’re there yet in general with these code tools in terms of the precision editing that you want to do. […] I think still the gold standard for me is just being able to drag stuff around. And you can do a lot with a click that would take you a hundred words to write and to really precisely nail. No one wants to prompt for the exact hex code or the shade of yellow and that kind of stuff. That’s just easier to just quickly do and directly manipulate.

Seiz isn’t anti-AI. His team pulls production code into Figma via MCP, edits it visually, and pushes it back to the codebase. He’s bullish on what that does to the old workflow:

It’s definitely changed our workflows in a way that it’s really blown up what a workflow even is. Before, for the majority of our careers, we’ve had a very linear, agreed-upon workflow where you increase fidelity as you go on. Because it’s really expensive to work in code, and it’s really cheap just to trade ideas and sketch them out. But AI basically collapsed that, and it’s just as cheap to riff in code as it is to riff in design.

The cost of exploration collapsed. The need for direct manipulation didn’t. Both can be true.

How Figma engineers sync designs with Claude Code and Codex

Most teams are still passing static design files back and forth, and most Figma files are already out of date by the time they reach engineering. Gui Seiz (designer) and Alex Kern (engineer) from Figma walk through the exact workflow their team uses to bridge that gap with AI, live onscreen. They…

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