According to Harvard Law School, Eric Ries tells Lenny Rachitsky, only 20% of venture-backed founders are still CEO three years after going public. Every founder gets told by their lawyers, bankers, and VCs that they’re the exception. Statistically, they’re not. Ries, author of the Silicon Valley textbook The Lean Startup, treats this as a structural problem with a structural answer in his new book Incorruptible. The analogy he spins:

This is like you’re building a bridge. And if your bridge collapses, and Lenny, I say you’re an engineer, and I say, “Lenny, why did my bridge collapse?” If you’re like, “Well, ‘cause of gravity.” I’m gonna be like, “Dude, yeah. Thank you for that genius insight, right?” […] I call it financial gravity. […] Yeah, but I want to know why did this bridge collapse? And more importantly, how come other bridges didn’t collapse? And they say, “Oh, for that, we need to study the load, load factor, wind load, shearing tension.” And we go look up close. We say, “Oh, look, all the metal bolts have been corroded.” They’re rusted. No wonder it collapsed. And then if you say, “Well, I want to build a new bridge, but I don’t want this one to collapse. What can I do?” You won’t say, “Well, gravity, what can you do?” No. You say, “Why don’t we use stainless steel next time on the bolts so they don’t get corroded?” Oh, yeah, good idea. So this book is about what are the organizational equivalents of stainless steel?

This is the move that makes Incorruptible a design book. Most writing about founder ouster and mission drift treats those outcomes as moral failures: bad people taking shortcuts or unlucky breaks in the market. Ries refuses that. Corrosion is predictable. Stainless steel is a material choice. Your bolts are going to rust unless you specified otherwise before pouring the foundation. The governance documents a founder signs in year one are the structure of the company itself. And the people advising them on those documents (the lawyers, the bankers, the VCs) are not the people who will be standing on the bridge in year ten.

Ries on a related diagnosis:

I could tell that this restaurant got taken over by private equity. I could taste it. And I’ve told that story a bunch of times now. And so many different people have told me, “Oh yeah, I know what restaurant you’re talking about!” And then they name like 12 different restaurants. So what’s going on that like you can taste the ownership structure of a company in the food? How many people have had a famous brand that they love get ruined? […] all kinds of famous companies where the thing that destroyed them was not competition. It was not someone else came up with a better product. No, their very success became a liability because the more gold in the goose, the greater the temptation to butcher.

You can taste the ownership structure in the food. That’s a designer’s instinct, even if Ries doesn’t call it that. It’s the same thing that tells you, holding a product, whether the team that built it still cares, and whether anyone at the top is protecting the people who do. The Sonos app rewrite that wiped half a billion in market value came from decisions inside the company about what to ship and who got protected. The bridge was already corroding. Ries is arguing that the protection has to be installed early, before there’s anything worth butchering. That’s design work, in the most literal sense.

Ries is a captivating storyteller in this episode. I can’t wait to get my hands on his new book.

When I wrote about the forward-deployed designer squad model earlier this year, I was working from the outside in: what the model should look like, who it serves, why it matters. Ron Bronson ran it for four years as director of a 40-person design division at 18F, the now-defunct US government’s in-house digital services agency. His post is the inside view and he diagnoses why most orgs never get there:

The real reasons that design roles aren’t being considered for this is the ways orgs constrain how designers show up on cross-functional teams. If your designers are only good for handoffs, you’re not going to invest in the headcount.

The people are the key, but you have to be opinionated about what you’re looking for your designers to do. If you’re looking for pixel-perfect, portfolio polish then you’re doing it wrong. Due to the quirks of federal hiring rules, we weren’t allowed to consider portfolios. It didn’t mean we couldn’t look at them, they just couldn’t be part of the criteria someone got an offer or not.

Take the portfolio rule: federal hiring restrictions sound like the kind of constraint that makes a practice worse, and instead they forced 18F to evaluate designers on the things that actually predict forward-deployed performance—ambiguity tolerance, collaboration, low ego, willingness to work in the open. The portfolio gauntlet that dominates tech-industry design hiring optimizes for the opposite skill: producing pixel-perfect artifacts in isolation. Bronson’s team got better signal because they were prevented from looking at the worse one.

Bronson on the multidisciplinary bar:

hired designers who can do more than one thing. Some impressive UX researchers would show up on our doorstep often, and if they talked to me, I’d be very direct with them about how we worked and that our designers often had to wear more than one hat out of necessity. The other constraint? Headcount. Design often has to justify itself more than other practices, so we couldn’t afford people who were too “special” to be staffed to a broad array of partner engagements. What this meant in practice? Designers who could code, researchers with content strategy & information architecture chops, service designers who could lead and/or PM projects, and every designer being a strategist on some level.

Generalist breadth in this context is a structural requirement of the engagement. That’s what Bronson means by “wear more than one hat out of necessity.” You can’t deploy a specialist into a six-week problem-scoping sprint and expect them to be useful for more than one week of it.

Bronson on where designers should sit:

As I explained in Design as Repair at IxDA Oslo last September: we need designers embedded where problems happened, not downstream after it’s been scoped, broken and all the framing has been done and asked to execute.

Most design orgs are structurally downstream: invited in after PM and engineering have already decided what’s being built, given a brief that pre-resolves the questions design should be asking. Bronson’s 18F was built to refuse that posture by default, which is why the model worked there before it had a name.

Luke Wroblewski shared his notes from the Design Futures Assembly, a gathering of about a hundred senior designers and leaders from AI labs, big tech, and startups in San Francisco:

When everyone can ship, you get a different kind of problem. One design leader described it perfectly: they let everyone build and push whatever they wanted. And you could feel it in the product, because nothing made sense together.

This is the part of the AI-in-design story that the toolkit numbers obscure. Wroblewski reports roughly half of designers had shipped AI-generated code to production this year, and that the typical designer’s toolkit had doubled in size over twelve months. Those are real numbers. But once production stops being the bottleneck, the bottleneck moves. A single word surfaced repeatedly:

Several people at the assembly used the word “editorial” to describe where design leadership is heading. Less about making the thing, more about deciding what gets made and ensuring it all holds together. The skill of saying no is becoming one of the most important skills in the profession.

The “saying no” line echoes something Chad Johnson wrote a few weeks back: the designers who shape direction “learn to say no with evidence and to disagree without drama.” The Assembly’s framing makes that posture mandatory at a portfolio level, not just on individual features. One tool company founder, Wroblewski notes, preferred “coherence”: the sense that a product came from one shared point of view. I like that word better too. Coherence describes the thing the user actually feels.

Scott Berkun lists three portable superpowers most designers underrate in themselves: investigative curiosity, the ability to translate between people who can’t understand each other, and a working grasp of tradeoffs. The first one is where he starts:

If we can spend hours reading about the 16th-century French history behind the beloved font Garamond, or studying the details of the design prototypes Jonathan Ives made to create the first iPhone, we have the rare capacity to discover and digest layers of complex information for practical use in solving problems.

Designers tend to file “I went deep on Garamond’s history” as a hobby or a tic, not a transferable skill. Berkun’s point is that the depth is the skill, and the subject is interchangeable. Aim it at a thing your CEO is worried about and you’re suddenly the person who knows the most about it in the room.

On translation:

Someone who explains things clearly, including through insightful sketches, diagrams, or metaphors, has tremendous value. Explainers help people make sense of each other. Designers are often shy about their ability to explain things, but typically we’re better at this than other professionals, since our work is rooted in communication (even visual design is rooted in semiotics, the study of symbols and their meaning). If we can be curious about our coworkers’ perspectives, objectives, and frustrations, we can be translators.

Berkun has made the curiosity argument before, in the negative, when he listed lack of curiosity as one of the five worst habits a designer can have. Reading this piece next to that one, the two halves connect: the habit he warns against in one post is the superpower he’s asking us to revive in this one.

In product orgs, the word “autonomy” tends to get attached to seniority and titles. Sara Paul, writing for Nielsen Norman Group, puts the bar somewhere else:

Our research shows that autonomy is about becoming sufficiently informed to credibly shape shared product decisions.

You’ve earned design autonomy when you’ve collected enough context to make a recommendation that holds up under scrutiny. Until then, you haven’t. Low-autonomy designers, in Paul’s terms, “execute predefined solutions.” High-autonomy designers shape what gets prioritized, because they know things their stakeholders don’t.

The four-part pipeline is the practitioner half:

The designers who achieved high autonomy kept information flowing to them from all sources within their organization. Their pipelines consisted of four parts: (1) Gathering information from across teams and channels, (2) Building relationships with people who provide information, (3) Creating crossfunctional spaces for information to be shared, (4) Synthesizing information to form a “big picture” of context that empowered credible recommendations.

Paul’s examples are specific enough to put to use. The opening one is a lead designer at an online review platform whose ad-setup experience lived across mobile, desktop, and web. Three teams owned different parts of the experience and the whole was nobody’s job. Here’s how the story ends:

She saw the problem, took the initiative to gather the information she needed, and synthesized it into a recommendation that boosted her influence over what got built. This is design autonomy.

None of this required a new title. It required a tracker, a few standing meetings, and the willingness to do the synthesis work nobody assigned.

The designers I want—and have—on my team are the ones who can fill in for a PM when they’re on vacation. Paul’s article is the mechanism for getting there. The PM-shaped skill is holding the information context that lets you make a defensible call.

(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.

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.

I published an article about the design talent crisis in Fast Company! The setup is what I’ve covered before on this blog extensively. But there’s a connection that I draw with the trades—the construction industry and how they have a solution that the design industry could learn from.

In the article, I write:

Construction has been running formal apprenticeship programs since the National Apprenticeship Act of 1937, and informally for centuries before that. The Department of Labor’s Registered Apprenticeship Programs enrolled roughly 940,000 people nationwide in fiscal year 2024. These aren’t casual internships. They’re structured, multi-year pathways that pair inexperienced workers with seasoned professionals and build skills through graduated responsibility. The retention numbers tell you everything: Apprenticeship programs report a 93% employee retention rate. For every $100 employers invest, they see an estimated $144 return.

The contractors I work with don’t debate whether to invest in their pipeline during a downturn. They know that if they stop training apprentices, they won’t have journeymen in four years, and they won’t have master tradespeople in 10. The pipeline is the business.

There’s a three-point plan to dig us out of this hole. But of course, it requires committments from design leaders and the C-suite:

1. Stop tying junior hiring to project demand
2. Formalize mentorship
3. Accept the short-term cost

There is more to the article. Please take a read and share!

The Sonos app disaster taught me something about roadmaps. Leadership kept adding initiatives—Sonos Radio, the Ace headphones—without ever naming what those additions displaced. QA got squeezed. Stability testing got cut. The designers who warned them were overruled. No leader said out loud what was being sacrificed to make room.

Yusuf Aytas names exactly this failure:

People like to talk about priorities as if the main problem is choosing what matters. In practice, the deterministic factor is capacity. Team capacity. System capacity. The share you lose to maintenance, interruptions, coordination, and keeping the machine fit to run. Ignoring these physical limits turns an ambitious roadmap into a collective illusion.

“Collective illusion.” That’s the right name for it. Aytas on where the dishonesty starts:

A new customer request appears. Leadership wants a visible bet. Sales needs something for a deal. Everyone talks about importance. Almost nobody says what gets pushed out. That is the real decision. They have only added pressure and left the team to absorb the contradiction later.

Aytas builds the whole piece around a carpentry metaphor—one saw, limited operators, timber that needs oiling and adjustment before it can be cut. Software hides the constraint better, but the physics are the same. There’s more in the piece on shaping work before it competes for capacity, using visible investment buckets, and why reallocation is never free.

AI tools made designers faster. The question nobody’s answering is whether their organizations can keep up.

Cameron Worboys, head of product design at Cash App, talking to Michael Riddering on Dive Club:

I think the biggest blockers across all of the tech industry in the next 2 years will not be the speed of building. It’s going to be the operational side and being able to move something from like we have built this thing. How does it move through the operational cogs of product development in order to like get it live to customers? So my view is like how do we set ourselves up for the new world? You have to make sure that your organization is capable at running at the same speed as the AI tools. And these AI tools move fucking fast.

The bottleneck migrated. Building isn’t the constraint anymore. Getting what you’ve built through approvals, reviews, compliance, and deployment is. Cash App’s response has been radical: they’ve flattened to three management layers (they call it “core plus three”), deleted design crits, and are pushing every designer to ship production code.

Worboys on what quality actually looks like at this speed:

The quality piece, there’s a misconception that it comes from a designer sitting in some cave for 3 months and pontificating about the future of software. It literally doesn’t. It comes from reps and the speed which you can be wrong and the speed that you can go again and experiment and experiment and experiment. And I think that’s what we’ve seen change, is the amount designers can produce has exponentially increased and the amount of like bureaucracy and layers you need to run an organization has changed a lot as well.

Quality through iteration, not pontification. That’s always been true, but when each iteration takes minutes instead of days, the gap between teams that ship and teams that sit in review becomes enormous.

Worboys on where this leads:

I believe one of the primary ways which you will create lock-in in the new world is creating apps that feel completely one of one. […] When you think about the future of software development and where it’s going with generative UI, there is nothing in the future that’s going to prevent us from creating these completely one of one experiences. So that’s what is top of mind for me at the moment. And I do think we will get there relatively quickly, that every Cash App does feel unique and completely designed around the person. And then from a business perspective, it creates this deeper, harder to quantify emotional connection with a product that is the same as like your wardrobe. Clothes are by and large like an expression of personal identity.

This is the most concrete product bet I’ve seen on generative UI. Not widgets inside a chat window. Entire apps shaped around the individual. I still think core app chrome should stay stable. But Worboys is betting that consumer fintech is where that line starts to blur.

Why AI isn’t showing up in productivity data? Chetan Dube offers one answer in Fast Company: most companies are bolting AI onto existing roles instead of redesigning the work.

Most managers are using AI the same way they use any productivity tool: to move faster. It summarizes meetings, drafts responses, and clears small tasks off the plate. That helps, but it misses the real shift. The real change begins when AI stops assisting and starts acting. When systems resolve issues, trigger workflows, and make routine decisions without human involvement, the work itself changes. And when the work changes, the job has to change too.

McKinsey data backs this up—78% of organizations now use AI in at least one function, “though some are still applying it on top of existing roles rather than redesigning work around it.” That’s the Solow paradox in one sentence.

Dube’s lost luggage example is a good one:

Generative AI can explain what steps to take to recover a lost bag. Agentic AI aims to actually find the bag, reroute it, and deliver it. The person that was working in lost luggage, doing these easily automated tasks, can now be freed to become more of a concierge for these disgruntled passengers.

The job goes from processing to judgment. And if leaders don’t get ahead of it:

If leaders don’t redesign the job intentionally, it will be redesigned for them, by the technology, by urgent failures, and by the slow erosion of clarity inside their teams.

That slow erosion of clarity is already visible. People less and less sure what they’re supposed to be doing because the tasks they were hired for are quietly handled by a system nobody put in charge.

Earlier I linked to Hardik Pandya’s piece on invisible work—the coordination, the docs, the one-on-ones that hold projects together but never show up in a performance review. Designers have their own version of this problem, and it’s getting worse.

Kai Wong, writing in his Data and Design Substack, puts it plainly. A design manager he interviewed told him:

“It’s always been a really hard thing for design to attribute their hard work to revenue… You can make the most amazingly satisfying user experience. But if you’re not bringing in any revenue out of that, you’re not going to have a job for very much longer. The company’s not going to succeed.”

That’s always been true, but AI made it urgent. When a PM can generate something that “looks okay” using an AI tool, the question is obvious: what do we need designers for? Wong’s answer is the strategic work—research, translation between user needs and business goals. The trouble is that this work is the hardest to see.

Wong’s practical advice is to stop presenting design decisions in design terms. Instead of explaining that Option A follows the Gestalt principle of proximity, say this:

“Option A reduces checkout from 5 to 3 steps, making it much easier for users to complete their purchase instead of abandoning their cart.”

You’re not asking “which looks better?” You’re showing that you understand the business problem and the user problem, and can predict outcomes based on behavioral patterns.

I left a comment on this article when it came out, asking how these techniques translate at the leadership level. It’s one thing to help individual designers frame their work in business terms. It’s another to make an entire design org’s contribution legible to the rest of the company. Product management talks to customers and GTM teams. Engineering delivers features. Design is in the messy middle making sense of it all—and that sense-making is exactly the kind of invisible work that’s hardest to put on a slide.

Every team I’ve ever led has had one of these people. The person who writes the doc that gives the project its shape, who closes context gaps in one-on-ones before they turn into conflicts, who somehow keeps six workstreams from drifting apart. They rarely get the credit they deserve because the work, when it’s done well, looks like it just happened on its own.

Hardik Pandya writes about this on his blog. He shares a quote from a founder friend describing his most valuable employee:

“She’s the reason things actually work around here. She just… makes sure everything happens. She writes the docs. She runs the meetings that matter. She talks to people. Somehow everything she touches stays on track. I don’t know how I’d even describe what she does to a person outside the company. But if she left, we’d fall apart in a month. Maybe less.”

I’ve known people like this at every company I’ve worked at. And I’ve watched them get passed over because the performance system couldn’t see them. Pandya nails why:

When a project succeeds, credit flows to the people whose contributions are easy to describe. The person who presented to the board. The person whose name is on the launch email. The person who shipped the final feature. These contributions are real, I’m not diminishing them. But they’re not more real than the work that made them possible. They’re just easier to point at.

Most organizations try to fix this by telling the invisible workers to “be more visible”—present more, build your personal brand internally. Pandya’s advice goes the other direction, and I think he’s right:

If you’re good at the invisible work, the first move isn’t to get better at visibility. It’s to find the leader who doesn’t need you to be visible.

As a leader, I take this as a challenge. If someone on my team is doing the work that holds everything together, it’s my job to make sure the organization sees it too—especially when it doesn’t announce itself.

I became an associate creative director (ACD) in 2005, ten years after I started working professionally. I was hired by the digital agency Organic into that role. I remembered struggling mightily with trusting my team to do the work. In my previous job as an art director, I hated it when my ACD or CD would go into my files after I’d gone home and just redo stuff. I didn’t do that, but it was very difficult to fight the urge or to avoid designing my own direction. (I failed on the latter.) That’s an intrinsic problem.

Sometimes, the issue is extrinsic, especially when you’re promoted into a leadership role from being an individual contributor (IC). The transition is a struggle. You get promoted because you were great at the work, and then the organization keeps pulling you back to do the work instead of leading at the level your new role demands.

Sabina Nawaz, writing for Harvard Business Review, explains why promotions grant potential but not always permission:

Research shows many midlevel and senior leaders still spend a disproportionate amount of time on tactical work rather than enterprise leadership. In my coaching work with senior leaders, I’ve found that while promotions provide the potential to lead strategically, they don’t always grant permission to do so. To gain that, you must do the hidden (and harder) work of redefining how you think, behave, and interact within the system.

That phrase, “potential but not permission,” is the whole problem in four words. You have the title, but the org’s muscle memory keeps treating you like your old self.

Nawaz identifies a common culprit: bosses who can’t let go of their former role:

Because the SVP had personally run my client’s division for years, he struggled to let go of intervening in the VP’s work. Six months into the transition, the SVP was still reviewing every decision, overriding calls, and re-engaging in tactical discussions he no longer needed to oversee. While he explained his involvement as giving feedback and advice, he was “overhelping,” a seemingly benign act that research suggests can ultimately erode trust, autonomy, and performance.

I’ve watched this pattern derail design organizations. A new creative director gets promoted, but the VP who used to hold that role keeps jumping into design reviews, redlining layouts, second-guessing type choices. The CD never develops their own judgment because their boss never leaves the room.

Nawaz’s advice for breaking the cycle is direct:

Take a quick glance at your calendar and ask yourself if it still reflects the activities, information flow, and ownership items of your prior role. Just as you need your boss to step back to empower you, you must redesign where you spend your time and which decisions to let your team fully own.

Your calendar doesn’t lie. If it’s packed with the same meetings you attended before your promotion, you haven’t actually made the transition. You’ve just added a new title to your old job.

It’s January and by now millions of us have made resolutions and probably broken them already. The second Friday of January is known as “Quitter’s Day.”

OKRs—objectives and key results—are a method for businesses to set and align company goals. The objective is your goal and the KRs are the ways to reach your goals. Venture capitalist John Doerr learned about OKRs while working at Intel, brought it to Google, and later became the framework’s leading evangelist.

Christina Wodtke talks about how to use OKRs for your personal life, and maybe as a way to come up with better New Year’s resolutions. She looked at her past three years of personal OKRs:

Looking at the pattern laid out in front of me, I finally saw what I’d been missing. My problem wasn’t work-life balance. My problem was that I didn’t like the kind of work I was doing.

The key results kept failing because the objective was wrong. It wasn’t about balance. It was about joy.

This is the second thing key results do for you: when they consistently fail, they’re telling you something. Not that you lack discipline—that you might be chasing the wrong goal entirely.

And I love Wodtke’s line here: “New Year’s resolutions fail because they’re wishes, not plans.“ She continues:

They fail because “eat better” and “be healthier” and “find balance” are too vague to act on and too fuzzy to measure.

Key results fix this. Not because measurement is magic, but because the act of measuring forces clarity. It makes you confront what you actually want. And sometimes, when the data piles up, it reveals that what you wanted wasn’t the thing you needed at all.

I really appreciate the perspective of Lai-Jing Chu here as a Silicon Valley veteran. The struggle to prove the value of design is real.

I don’t know another function or role in the tech industry where it seems like we have to do our jobs at the same time as — and I will avoid saying “demonstrating value” here because it’s more than that — we carry out some sort of divine duty to make the product (let alone the world) a better place through our creativity.

Instead of more numbers like ROI calculations, Chu argues for counterintuitive approaches for advocacy, “not more left-brain exercises.”

Chu introduces us to W. Edwards Deming, an influential management consultant who wrote:

The most important figures needed for management of any organization are unknown and unknowable, but successful management must nevertheless take account of them.

One strategy she offers is to ask leadership a common-sense question: How would you grade the design?

Because when was the last time anyone did the most basic thing — to stop for a moment, hold the product in their hands, and take a good hard look at it? These questions throw the ball back in their court. It makes them wonder what they can do to help. Because chances are, most leaders want their product to have a good user or customer experience and understand that it makes a difference to their business success. You don’t just want buy-in — you want them to have true ownership.

I admire this approach, because chances are, leaders are already hearing about UX issues from customers. But to put this into practice in, let’s say, at any startup post-Series A will be an issue. There’s a lot of coordination and alignment that needs to happen because exec-level attention is much harder to come by.

Echoing my series on the design talent crisis and other articles warning against the practice of cutting back on junior talent, Vaughn Tan offers yet another dimension: subjective decision-making skills are only honed through practice. But the opportunities given to junior staff for this type of decision-making are slim.

But to back up, here’s Tan explaining what subjective decision-making is:

These are decisions where there’s no one “correct” answer and the answers that work can’t be known in advance. Subjective decisionmaking requires critical thinking skills to make strongly reasoned arguments, identify appropriate evidence, understand the tradeoffs of different arguments, make decisions that may (or may not) be correct, and develop compelling narratives for those decisions.

While his article isn’t about AI nor is it about companies not hiring juniors, it is about companies not developing juniors and allowing them to practice this type of decision-making in low-stakes situations.

Critical thinking and judgment require practice. Practice needs to be frequent, and needs to begin at a low level with very few consequences that are important. This small-scale training in subjective decisionmaking and critical thinking is the best way to learn how to do it properly in more consequential situations.

If you wait until someone is senior to teach judgment, their first practice attempts have serious consequences. High-stakes decisionmaking pressure cannot be simulated realistically; learning how to deal with it requires actual practice with real consequences that progressively increases in scope and consequentiality.

And why is this all important? Not developing junior staff means there will be a bottleneck issue—only seniors can make these judgement calls—and one day, there will be a succession problem, i.e., who takes over when the seniors leave or retire.

This short article could easily fall under the motivational category, but I couldn’t help but draw parallels to what we do as designers when working as part of a product team.

Hazel Weakly says that people who see systems also tend to become in charge of them, sooner or later. And to be a leader is to “understand that you’ll find yourself stranded in the middle of the ocean one day.”

Not just you, but everyone you lead. And you’ll need to chart a course. In the ever-changing winds, the ever-shifting tides, the unknown weather, and with an inability to see up or down or basically anywhere except a few minutes away. You won’t have the time to find your bearings even if you could. Yet, somehow, in this sea of swirling and infinite complexities and probabilities, in the midst of incalculable odds, you will find yourself needing to have simultaneously several different things…

The first thing is that you will fail. I equate this to knowing that design is about trial and error, testing and measuring, and then adjusting.

The second thing is unshakable conviction that “you will succeed.” I see success as solving the problem, coming up with a solution that helps users do what they need. And you know what? Designers will succeed when they follow the design process.

Finally, the third thing is to “prepare and make ready everyone around you.” Which means influencing your product and engineering counterparts and other stakeholders that the solution your advocating for is the right one.

As regular readers will know, the design talent crisis is a subject I’m very passionate about. Of course, this talent crisis is really about how companies who are opting for AI instead of junior-level humans, are robbing themselves of a human expertise to control the AI agents of the future, and neglecting a generation of talented and enthusiastic young people.

Also obviously, this goes beyond the design discipline. Annie Hedgpeth, writing for the People Work blog, says that “AI is replacing the training ground not replacing expertise.”

We used to have a training ground for junior engineers, but now AI is increasingly automating away that work. Both studies I referenced above cited the same thing - AI is getting good at automating junior work while only augmenting senior work. So the evidence doesn’t show that AI is going to replace everyone; it’s just removing the apprenticeship ladder.

From the Sep 2025 Harvard University paper, “Generative AI as Seniority-Biased Technological Change: Evidence from U.S. Résumé and Job Posting Data.” (link)

And then she echoes my worry:

So what happens in 10-20 years when the current senior engineers retire? Where do the next batch of seniors come from? The ones who can architect complex systems and make good judgment calls when faced with uncertain situations? Those are skills that are developed through years of work that starts simple and grows in complexity, through human mentorship.

We’re setting ourselves up for a timing mismatch, at best. We’re eliminating junior jobs in hopes that AI will get good enough in the next 10-20 years to handle even complex, human judgment calls. And if we’re wrong about that, then we have far fewer people in the pipeline of senior engineers to solve those problems.

Hard to believe that the very first fully computer animated feature film came out 30 years ago. To say that Toy Story was groundbreaking would be an understatement. If you look at the animated feature landscape today, 100% is computer-generated.

In this re-found interview with Steve Jobs exactly a year after the movie premiered in theaters, Jobs talks about a few things, notably how different Silicon Valley and Hollywood were—and still are.

From the Steve Jobs Archive:

In this footage, Steve reveals the long game behind Pixar’s seeming overnight success. With striking clarity, he explains how its business model gives artists and engineers a stake in their creations, and he reflects on what Disney’s hard-won wisdom taught him about focus and discipline. He also talks about the challenge of leading a team so talented that it inverts the usual hierarchy, the incentives that inspire people to stay with the company, and the deeper purpose that unites them all: to tell stories that last and put something of enduring value into the culture.  

And Jobs in his own words:

Well, in this blending of a Hollywood  culture and a Silicon Valley culture, one of the things that we encountered was  that the Hollywood culture and the Silicon Valley culture each used different models of  employee retention. Hollywood uses the stick, which is the contract, and Silicon Valley  uses the carrot, which is the stock option. And we examined both of those in really pretty  great detail, both economically, but also psychologically and culture wise, what kind of  culture do you end up with. And while there’s a lot of reasons to want to lock down your  employees for the duration of a film because, if somebody leaves, you’re at risk, those  same dangers exist in Silicon Valley. During an engineering project, you don’t want to lose people, and yet, they managed to evolve another system than contracts. And we preferred the Silicon Valley model in this case, which basically gives people stock in the company so that we all have the same goal, which is to create shareholder value. But also, it makes us constantly worry about making Pixar the greatest company we can  so that nobody would ever want to leave. 

Something that I think a lot about as a design leader is how to promote the benefits of design in the organization. Paul Boag created this practical guide to guerrilla internal marketing that builds a network of ambassadors across departments and keeps user-centered thinking top of mind.

Boag, writing in his newsletter:

You cannot be everywhere at once. You cannot attend every meeting, influence every decision, or educate every colleague personally. But you can identify and equip people across different departments who care about users and give them the tools to spread UX thinking in their teams.

This is how culture change actually happens. Not through presentations from the UX team, but through conversations between colleagues who trust each other.

We’ve been hearing a lot about AI agents and now enough time has passed that we’re starting to see some learnings in industry. Writing in Harvard Business Review, Linda Mantia, Surojit Chatterjee and Vivian S. Lee showcase three case studies of enterprises that have deployed AI agents.

They write about Hitachi Digital and how they deployed an AI agent as the first responder to the 90,000 questions employees send to their HR team annually.

Every year, employees put over 90,000 questions about everything from travel policies and remote work to training and IT support to the company’s HR team of 120 human responders. Answering these queries can be difficult, in part because of Hitachi’s complex infrastructure of over 20 systems of record, including multiple disparate HR systems, various payroll providers, and different IT environments.

Their system, called “Skye,” is actually a system of agents, coordinating with one another and firing off queries depending on the intent and task.

For example, the intent classifier agent sends a simple policy question like “What are allowed expenses for traveling overseas?” or “Does this holiday count in paid time off?” to a file search and respond agent, which provides immediate answers by examining the right knowledge base given the employee’s position and organization. A document generation agent can create employee verification letters (which verify individuals’ employment status) in seconds, with an option for human approval. When an employee files a request for vacation, the leave management agent uses the appropriate HR management system based on its understanding of the user’s identity, completes the necessary forms, waits for the approval of the employee’s manager, and reports back to the employee.

The authors see three essential imperatives when designing and deploying AI agents into companies.

1. Design around outcomes and appoint accountable mission owners. Companies need to stop organizing around internal functions and start building teams around actual customer outcomes—which means putting someone in charge of the whole journey, not just pieces of it.
2. Unlock data silos and clarify the business logic. Your data doesn’t need to be perfect or centralized, but you do need to map out how work actually gets done so AI agents know where to find things and what decisions to make.
3. Develop the leaders and guardrails that intelligent systems require. You can’t just drop AI agents into your org and hope for the best—leaders need to understand how these systems work, build trust with their teams, and put real governance in place to keep things on track.

Remote work really exploded when the Covid-19 pandemic hit. Everyone had to adjust to working from home, relying on Zoom and Slack and other collaborative tools much more. But beyond tooling, there’s also process. Matt Mullenweg, CEO of Automattic, has famously been a proponent of distributed work for a while.

Paolo Belcastro peels back the curtain to share how the 1,500 or so global employees of Automattic stay connected via two core principles:

There are two ideas that define our communication culture:

Radical Transparency: we default to openness, with every conversation accessible to everyone in the company. Asynchronous by Design: we don’t expect everyone to be “on” at the same time.

Everything is written down:

Our internal platform, P2, started life as a WordPress theme (it was called Prologue, later updated to version 2 and eventually shortened to P2) that lets people post directly on the front end of a site—fast, simple, and visible to everyone. Over time it evolved into a network of thousands of P2s for teams, projects, and watercooler chats (couch surfing, classified ads, house renovations, babies, pets, music, or games, we kind of have it all).

…

Every post, every comment, every decision ever made in the history of Automattic is preserved there.

As you can imagine, it soon becomes a volume problem. There’s too much stuff.

No one can read everything.

That’s why onboarding is designed to help people adapt:

• Each newcomer is paired with a mentor from a different team, to give them a cross-company perspective.
• They receive a curated list of “milestone posts” that map the history of Automattic, along with role-specific threads relevant to their work.
• The Field Guide offers principles, templates, and advice about how to handle communication.

Somehow, they make it work.

Building on Matthew Ström-Awn’s argument that true quality emerges from decentralized, ground-level ownership, Sean Goedecke writes an essay exploring how software companies navigate the tension between formalized control and the informal, often invisible work that actually drives product excellence.

But first, what does legibility even mean?

What does legibility mean to a tech company, in practice? It means:

• The head of a department knows, to the engineer, all the projects the department is currently working on
• That head also knows (or can request) a comprehensive list of all the projects the department has shipped in the last quarter
• That head has the ability to plan work at least one quarter ahead (ideally longer)
• That head can, in an emergency, direct the entire resources of the department at immediate work

Note that “shipping high quality software” or “making customers happy” or even “making money” is not on this list. Those are all things tech companies want to do, but they’re not legibility.

Goedecke argues that while leaders prize formal processes and legibility to facilitate predictability and coordination, these systems often overlook the messier, less measurable activities that drive true product quality and user satisfaction.

All organizations - tech companies, social clubs, governments - have both a legible and an illegible side. The legible side is important, past a certain size. It lets the organization do things that would otherwise be impossible: long-term planning, coordination with other very large organizations, and so on. But the illegible side is just as important. It allows for high-efficiency work, offers a release valve for processes that don’t fit the current circumstances, and fills the natural human desire for gossip and soft consensus.