Writing

Notes on design and AI.

Short, sharp pieces on leading design, building with AI, and doing the work myself. Newest first.

October 2026

9 min read · Fractional · Design Leadership · Startups · ConsultingAgency retainer or fractional design lead: you are buying decisions, not deliverables.Two proposals, one desk. A monthly agency retainer sells you capacity, a fractional head of design sells you judgment and ownership, and the retainer always looks like more per dollar. Here is what each one really costs a seed to Series B company, what each one owns, the roadmap test that picks between them, and the cases where I will tell you to sign the retainer.Read 12 min read · Design Leadership · AI · Strategy · Future of WorkParkinson’s Law is why AI has not made your team faster.AI collapsed how long the work takes and left how long you gave it completely untouched. Parkinson’s Law explains the rest: work expands to fill the time you allot it, so the weeks you saved turn into revisions nobody asked for. Here is the deadline discipline that converts cheap execution into shipped work, and the cases where a long timeline is still the right call.Read 12 min read · AI-First Design · Product Design · AI · Design LeadershipYour AI feature probably does not need a chatbot.A chat box is the fastest AI feature to build and the easiest one to ignore, because it hands the hardest part of the job, knowing what to ask for, to your customer. The AI products that get used hide the model inside an interface people already understand. Here is what to build instead, the four shapes to reach for first, and the narrow cases where chat really is the right call.Read

September 2026

10 min read · Hiring · Craft · Design Leadership · Product DesignTaste is not a vibe. Hand a designer real work and score the critique.Taste is the most predictive thing about a designer and the one signal most hiring loops never measure, because everyone treats it as a feeling. It is not. Put a candidate in front of your own shipped product, ask them to find what is wrong and rank it, and score the answer against a key you wrote first. Here is the exercise, the tells, and when the portfolio is still the better instrument.Read 12 min read · Design Leadership · Team Building · Design Operations · StrategyPlan your design team at 80%. A team booked to 100% can only react.The number that decides whether your design team gets ahead of the business is not headcount. It is the share of each week you actually assign. Book all of it and every urgent ask becomes a late night, every new tool goes unlearned, and the roadmap shows up already written by somebody else. Here is how I run a seven-person team at about 80%, what the open time actually buys, and the cases where running hot is the right call.Read 10 min read · Metrics · Design ROI · Design Leadership · StrategyNPS is not a design metric. Take it off the deck.A Net Promoter Score on a design scorecard is noise wearing a suit. It answers a question about your whole company, it moves for reasons nobody on your design team touched, and the people who invented it have since bolted a second number onto it. Here is what design should report instead, how to stand it up in a quarter, and the places NPS genuinely earns its slide.Read 10 min read · Design Leadership · Craft · Hiring · AI-First DesignA head of design who stops shipping loses the room.The design leader you hire will either keep making things or stop. The one who stops forfeits the authority to judge the work, because the cost of every decision moved and they are still quoting last year’s prices. Here is what still shipping means on a real leadership calendar, the three questions that test for it in a hire, and the cases where a hands-off leader is genuinely the right call.Read 9 min read · Startups · Hiring · Design Leadership · Team BuildingBefore Series A, hire one designer who does everything.One generalist who can research, design, and ship is the only design hire that pays for itself before Series A. Every specialist role you add early buys depth you cannot use yet and a handoff you have to manage forever. Here is the hire to make, how to rent the specialist work instead, and the cases where specializing early is genuinely right.Read 9 min read · AI-First Design · Design Process · Prototyping · Design LeadershipFigma stopped being the deliverable.On an AI-first team the output of design is a working prototype in code, not an annotated handoff file. The hours spent perfecting the file are the slowest part of your process, and they buy you a promise where you could have had evidence. Here is the standard to hold your team to, what it changes operationally, and the cases where the file really is still the deliverable.Read 9 min read · AI · Design Leadership · AI-First Design · StrategyWhat AI still cannot do in design, and why that is where the value moved.AI is genuinely good at the middle of the work: drafts, variations, production, the polish pass that used to eat a week. It is bad at deciding what is worth building, and it cannot carry the consequences when the thing ships. Here is the honest map of both, and what it means for where a leader spends the hours and the budget.Read 11 min read · Hiring · Design Leadership · AI · CraftStop running portfolio walkthroughs. Here is the interview I run instead.AI makes any screen look good, so a portfolio walkthrough tells you almost nothing about the person who made it. Hand a candidate a real, ambiguous problem for ninety minutes and watch whether they can scope it, build something that runs, and cut. Here is the brief, the tells, and when to keep the walkthrough instead.Read

August 2026

10 min read · Fractional · Design Leadership · Hiring · StartupsDo not hire a fractional head of design if you need someone in the room every day.Fractional design leadership is senior judgment bought on a schedule. It cannot build culture daily, and it cannot be in the unplanned room where the real tradeoffs get settled. If that is your actual gap, two days a month will not close it. Wait, and hire full-time.Read 7 min read · Career · AI · Craft · DesignPassion is built, not found."Follow your passion" is the worst career advice for designers right now. Cal Newport had it right: build a rare, valuable skill first and the passion, the autonomy, and the work you actually want all follow. Waiting to feel inspired before you commit is the thing keeping you mediocre, and in the AI era the craftsman who builds compounds while the passion-chaser keeps job-hopping.Read 4 min read · AI · Future of Work · Career · CraftGet comfortable being uncomfortable.The tools now change faster than anyone can master them, so the discomfort of learning never really ends. That feeling is not a warning. It is the signal that you are on the edge where the value is.Read 9 min read · AI · MCP · Engineering · AgentsHow I build an MCP a team will actually use (the rules go in the server).A demo that dazzles and a V1 a team trusts are not the same build. The difference is where the rules live. Put your brand voice, your price floor, your no-invented-data guarantee in the model’s prompt and the agent will break them on a bad day. Put them in the server and it physically cannot. Here is how I build the second kind.Read 8 min read · AI · Design Leadership · Design Systems · MCPWhat I actually do with AI as a design leader (it isn’t prompts).’AI-first’ is theater until someone builds the plumbing. The leverage is not a more clever prompt. It is wiring your real systems, your design tokens, your product data, your internal tools, straight to agents so the work drops from weeks to minutes. Here is the plumbing, and who has to lay it.Read 4 min read · AI · Automation · Future of Work · StrategyWe are building time machines.The real product of automation is not speed, it is time given back. Point AI at the tedious, high-effort work and you hand people their hours back for the decisions only they can make.Read 7 min read · AI · MCP · Engineering · ProductWhat an MCP actually is, and why ’the new API’ misses the point.You keep hearing ’MCP is the new API’ and never a straight answer. It is a wrapper around the APIs you already have, not a new kind of one. The protocol is the boring part. The real shift is the interface: you stop hunting through a UI for thirty minutes and ask for what you need in one plain sentence.Read 8 min read · Design ROI · Strategy · Metrics · Design LeadershipWhy most design ROI decks lie, and how to build a credible one.The confident single-number slide wins the first meeting and loses the CFO. The credible deck names three things: what design moved, what it did not, and what you cannot separate. Here is how to build it.Read 7 min read · AI · Product · Founder · StrategyHow I evaluate an AI product idea before building it.The one question I run every AI idea through before writing code: does it do something that was impossible two years ago? If not, it is a feature in a company’s clothes, and the incumbent wins. Here is the wedge, the only-AI-can-do test, and the real kill list.Read 7 min read · Design Debt · Design Leadership · DesignOps · StrategyDesign debt is real debt.Design debt loses every roadmap fight because no one ever priced it. Put it in dollars and hours, keep a register the way finance keeps a debt schedule, and you get a clear rule for when paying it down beats shipping the next feature.Read 8 min read · Design Systems · Design Leadership · DesignOps · StrategyWhen to kill a design system instead of scaling it.A system is supposed to make a small team move like a big one. Most teams scale it past that point and end up paying a full-time crew to maintain overhead. Here is how to tell, and how to wind one down without breaking the product.Read 10 min read · Fractional · Design Leadership · Startups · PlaybookShip by week three: the first 90 days as a fractional head of design.A month of listening is a full-time leader’s luxury, not a fractional one’s. Here is what to audit, what to leave alone, and what to put in front of the business early enough to earn the rest of the quarter.Read 6 min read · AI · AI-First Design · Future of Work · StrategyExecution has become cheap, ideas are more expensive than ever.AI made building nearly free, so the scarce thing now is knowing what to build. That is why the lines between design, engineering, and product are dissolving, and what it changes about how we work.Read

July 2026

11 min read · Consulting · Hiring · Design LeadershipWhat a design consultant does, and when to hire one.The job in plain terms, the four kinds of design consulting, the signals you actually need one, and how to scope a first engagement that pays for itself.Read 9 min read · Fractional · Hiring · Design LeadershipHow to hire a fractional design leader.What to look for, the questions that reveal a real leader, and how to scope the first engagement so you get value fast.Read 10 min read · Startups · Hiring · Design Leadership · FractionalWhen does a startup actually need a head of design?The signals that mean you are ready, the reasons that do not count, and why the first design leadership hire is usually fractional.Read 8 min read · Fractional · Hiring · Design Leadership · StartupsFractional design leader, design agency, or full-time hire: which fits your stage.The three real ways to get design help, what each actually gives you, and how to pick by the problem in front of you.Read 8 min read · Consulting · Hiring · Product DesignThe questions I would ask a product design firm before signing anything.Seven questions that separate firms that ship outcomes from firms that ship decks, from someone who has sat on every side of the pitch.Read 8 min read · Consulting · Product Design · MetricsWhat a product design firm costs, and where the money actually goes.The three pricing shapes, the overhead ratio nobody itemizes, and how to make any firm engagement cheaper without cheapening the work.Read

June 2026

9 min read · Fractional · Design Leadership · HiringWhat fractional design leadership actually costs, and how to budget for it.How fractional pricing really works, what drives it, and how to know you are getting your money’s worth.Read 12 min read · Strategy · Metrics · Design LeadershipHow to measure the ROI of design.A practical way to tie design work to numbers the business already cares about, without faking the math.Read 11 min read · Hiring · Design Leadership · Fractional · StartupsFractional or full-time design leader: which does your team need?A clear decision framework for when to hire a head of design full-time and when a few days a month is the smarter call.Read 12 min read · AI-First Design · Design Leadership · ToolsHow to choose AI tools for a design team.A buyer’s framework for picking AI tools your team actually adopts, instead of a pile of subscriptions nobody opens.Read 10 min read · AI-First Design · Design Leadership · AI AdoptionMost AI design transformations are theater.The hard part was never the tools. It is getting a team to actually change how it works, and keep working that way six months later.Read 10 min read · Design Leadership · AI-First Design · CraftI lead design, and I still build. That’s the job now.For years the industry told designers that leadership meant leaving the craft behind. AI made that advice dangerous.Read 10 min read · Design · AI · CareerThe gap between good and great isn’t skill anymore.It is curiosity, and the willingness to build something before anyone gives you permission.Read 10 min read · AI-First Design · Design Process · Design LeadershipWhat an AI-first design process actually looks like.Most teams bolt AI onto the end of the old process. AI-first changes the order of operations from the first hour.Read 12 min read · Design Leadership · Team Building · AI-First DesignHow to build a design team in the AI era.The org chart that worked in 2020 is the wrong shape now. Here is how I structure a team that moves at AI speed.Read

May 2026

10 min read · Design · AI · Craft · CareerThe most valuable designers now are the ones who build.For a decade the industry told designers to stop touching the tools. AI made that advice expensive.Read 11 min read · Hiring · Design Leadership · AI · CareerWhat I look for when I hire designers now.The cleanest portfolio is not the signal it used to be. Curiosity and nerve are.Read 10 min read · Design Leadership · Fractional · StartupsWhat a fractional head of design actually does.Not a consultant who makes slides. A senior leader who owns the work for a few days a month.Read 10 min read · AI · Design · Future of WorkAI will not replace designers. It will replace the design process.The fear is aimed at the wrong target. The job is not going away. The way we do it already is.Read

April 2026

12 min read · AI-First Design · Agentic AI · Product Design · Story GenieWe let AI agents make a children’s book, and kept humans in charge.How I designed trust into an AI-native product where agents do the production and parents still get something they are proud to give.Read 12 min read · Design Systems · AI-First Design · Design LeadershipDesign systems are the foundation AI builds on.Everyone wants AI to generate their UI. The teams that win are the ones whose system gives it something good to generate from.Read

March 2026

11 min read · Design Leadership · Strategy · MetricsHow I prove design actually moved the business.Design earns its seat by changing numbers, not by being pretty. Here is how I make the case.Read 9 min read · AI · Founder · Design Leadership · Story GenieWhy I founded an AI company while leading design.The best way to understand where our craft is going was to bet my own time on it.Read