The Model Is the Easy Part
Why the Kasparov experiment, not the model leaderboard, is the right way to think about AI at work.
Everything, organized by how you read.
The Model Is the Easy Part
Why the Kasparov experiment, not the model leaderboard, is the right way to think about AI at work.
The Release Type We Forgot
A beta-tag standoff that turned out to be about institutional memory, not policy.
Maintenance Isn't a Demotion
Splitting innovation from upkeep is clean on a whiteboard and quietly corrosive on a team.
The Question Before the Pixels
The most useful question in a crit is whether the work should exist at all.
Tone Is a Material
A leader's tone isn't a soft skill on top of the work. It's the material a team's resilience is built from.
The Bar Doesn't Move
Why a flooded candidate market is exactly when you hold the hiring bar highest.
When the Save Indicator Is Doing Two Jobs
A save indicator that tried to show two different states at once, and the rule it broke.
Why We Didn't Roll Back
A launch-day bug, and why the hotfix was the conservative call, not the brave one.
Org Follows Strategy
When a roadmap creates dread, the ambition usually isn't the problem. The missing resource conversation is.
Comma, Not a Bow
Two small moves that decide whether crit feedback actually changes the work.
Handshake, Not Handoff
A four-part recipe for getting useful work out of AI, and the ingredient most people skip.
AI Adoption Is a Manager Conversation
Why a top-down AI mandate backfires, and the channel that already carries weight.
Purple Was the Missing Dimension
A cross-functional color decision won on brand strategy rather than taste.
Naming Is Information Architecture
Why one capability with several names is an IA problem, not a branding one.
AI Agents Reward Decomposition, Not Delegation
The real bottleneck to AI adoption on design teams is task decomposition.
The AI Users Respond To Is the AI They Can't See
Holding the tension between an AI-forward brand and users who prefer AI unlabeled.
The Scalability Argument Hiding in a Color Choice
A crit about button placement was really a debate about information architecture.
The Cost of Being the Optimistic One
A leadership assessment, a hard piece of feedback, and the cost of optimism.
Taking Point on AI Adoption Inside the Product Org
94 percent of what?
Trust, Not Access
A clinical product I'm partnered on right now wanted to ship an open-ended AI query interface.
Start with the Controversial State
The wedge is conservative. The destination is bold. Putting them in that order is the right move.
Where the Work Went
The velocity dashboard lies by omission. It captures the part of the work that moved fast and nothing else.
I'm Not Backfilling Designer X
A designer in one of our squads is leaving the team. I'm not backfilling the role.
Sacred Ground
There were six of us in the room.
The Lockout Spectrum
A spectrum for any forced rollout, sketched on a whiteboard during a 2FA push.
Accuracy Is Not Usefulness
A correct number with no call to action is functionally invisible.
Disagree and Commit Upward
The hiring criterion that decided a senior loop, and that isn't on most rubrics.
The Carver and the Joints
A reading list anchored on Christopher Alexander's Notes on the Synthesis of Form.
Exact Copy Informs Design
Typography, spacing, and rhythm aren't properties of the structure. They're properties of the words inside it.
Designers Pushing Code, One Quarter In
Early signal from a six-designer pilot. The autonomous-agent demo isn't the right shape yet.
The Database Test for AI Strategy
When AI shows up as a pillar in a strategy diagram, ask whether the rest of the diagram could function without it. If not, you do not have a pillar. You have a substrate, and substrates do not go in the pillar row.
A Great Design Gathering
Seven ideas, six quotes, and one book recommendation from sixty design leaders in a SoMa space under the Chatham House Rule. The most useful frame: AI does not automate design, it exposes what design was actually responsible for in the first place.
The Power Share Paradigm: Function, Form, Scale
Non-designers are doing design work, and gatekeeping does not work in 2026. The job is to teach, in a specific order: function first, form second, scale third. What gets shared is the access. What gets kept is the bar.
Tying Infrastructure to Churn
Stop pitching infrastructure investment as revenue acceleration. Start pitching its absence as churn. The math is more honest, and the conversation moves from speed to durability, where design leaders tend to do better.
Saying No When You Can't Stop
There are three kinds of darling worth killing: feature, process, and personal. The discipline of stopping is harder than starting, and it is the rate-limiting skill in any craft-led practice.
The Vibe Tribe is a Job Now
The people building things outside the official roadmap are usually quiet, easy to miss, and producing the work that will redefine the practice in eighteen months. Curating them is a real leadership job in 2026.
Designing the Bridge Role in Two Phases
We are hiring a design technologist. But we are not hiring the version of the role we eventually want. We are hiring the version the team is ready for, in a deliberate first phase, with a second phase already scoped.
Lovely Poetry and Lots of Exciting Things
Two tech leaders on my team opened an org-wide planning presentation this week by promising we were about to get "lovely poetry and lots of exciting things." They were not being metaphorical.
The Shelf Behind the Keynote
The three non-design competencies I talk about most when people ask how to prepare for design leadership, and what I recommend for each.
When Disabled Is the Wrong Signal
A designer brought a promo-activation flow to crit this week. The team had reached for a disabled checkbox to handle a pending state. It was almost right, and almost right is usually the most interesting place to start a crit.
Leverage as a Leadership Posture
When a CEO asks for leverage in a compression quarter, the word is doing more work than it appears to. Most leaders read it wrong. Here is the generative version, the four questions that distinguish it from the extractive one, and why the posture is also the retention story.
The Feedback That Stopped
When a teammate goes silent, it is rarely maturity. It is almost always withdrawal. Here is what that looks like, why it is more dangerous than open conflict, and the bounded repair that got two designers back in a room with each other.
When the Launch Is Real and the Team Is Thin
The hardest part of a big launch is not the product work. It is holding the cross-functional orchestration layer together when the people assigned to it are missing, overloaded, or not senior enough for the scope.
Translating the Boardroom for the People Who Do the Work
Every Monday morning I rewrite the CEO update for my design org. Here is why, how I do it, and the template you can steal.
Building Design Outcomes: From Conversation to Live Site in Two Hours
I built a portfolio site for my design leadership work using Claude Design, Claude Code, and Vercel. The full process, the walls I hit, and what the publishing workflow looks like now.
When Building Gets Cheap, Carrying Gets Expensive
AI is making it faster to ship features. That is not the hard part anymore. The hard part is deciding what deserves to exist.
What Verbosity in an Interview Actually Tells You
A candidate gave strong answers with real substance. Every single one took twice as long as it needed to. How I evaluated that signal and what I recommended.
When the Structure Is the Problem, Not the Person
We had the right designer doing the right work. The coordination was still breaking down. Here is the meeting where we stopped blaming execution and started looking at the org chart.