Joshua McDonaldAug 20, 2026The Org Chart, the Tube Map, and Models That Are Wrong on PurposeAshby says a manager needs a model of their system. Every model is wrong. The London Tube map explains how both are true.
Joshua McDonaldAug 18, 2026Only Variety Can Absorb VarietyAshby’s law, the arithmetic of control, and why the manager is now the constraint
Joshua McDonaldAug 13, 2026AI Made Writing Code Nearly Free. Reviewing It Got 91 Percent Slower.Two and a half years of AI coding, as told by the industry’s own numbers, biases included
Joshua McDonaldAug 6, 2026The cost of changing your mind depends on two things: how fast feedback arrives, and how much got…Two cases, three shaky sources, and the two things that actually decide the cost of changing your mind
Joshua McDonaldAug 2, 2026Every Improvement Made No DifferenceTheory of Constraints, the lane drop at Clarksburg, and why local wins do not add up
Joshua McDonaldJul 30, 2026Adding People Reduced OutputThe Universal Scalability Law, cache coherence, restaurant kitchens, and the size at which an organization starts working against itself
Joshua McDonaldJul 27, 2026Everything Is 90 Percent DoneLittle’s Law, Kingman’s formula, and why the sprint board is full while nothing ships.
Joshua McDonaldJul 23, 2026Amdahl’s Law for Org ChartsWhat a three-page paper from 1967 explains about two-pizza teams, monoliths, and why your calendar time refuses to shrink
Joshua McDonaldJul 21, 2026What “Open Weight” Actually MeansA plain explanation of the version of AI you can download, keep, and run without asking anyone.
Joshua McDonaldJul 15, 2026You Can’t Compress What You Can’t GradeAdding an eval harness to TokenLens, and why it should have come before the compression work. A follow-up to “I Built a Prompt Compressor…
Joshua McDonaldJul 9, 2026I Built a Prompt Compressor. The Most Useful Thing It Found Was NothingWe’ve always compressed data to save time and money. What’s new isn’t the instinct. It’s that the codec is now a language model. That arc…
Joshua McDonaldJul 2, 2026Who Reviews the Reasoning?The code coming out of agents runs, and the reviewers shipping today catch the bugs. Nobody is reviewing the decision: was this the right…
Joshua McDonaldJun 28, 2026Do We Still Need the Sprint?What incremental delivery means, once the cost of an increment falls through the floor, whether the two-week cadence is still earning its…
Joshua McDonaldJun 18, 2026The Preflight Check for Distributed SystemsThe failure modes that take systems down, and where to look for each one
Joshua McDonaldJun 14, 2026How an Export Control Rule Reaches an AI Model Running in a US Data CenterWhat the directive on Fable 5 and Mythos 5 says, how deemed-export law works, and the 1991 precedent. Sourced to primary documents.
Joshua McDonaldJun 11, 2026Claude Skipped Idempotency Because I Never Asked. So I Made Asking Unnecessary.The code broke on a retry I never mentioned, and even when I ask for the fix, the first version is usually the wrong shape. The answer was…
Joshua McDonaldJun 9, 2026Why system design matters more as AI makes building fasterWhat AI still can’t reason about no matter how well you prompt it.
Joshua McDonaldJun 4, 2026robots.txt Told Crawlers Where to Stop. llms.txt Tells Agents Where to GoWhat the file does, how to write one, and why retrieval is the part that actually matters.
Joshua McDonaldMay 27, 2026What an Agent Skill Is, and How to Write OneIf you use an AI assistant for the same kind of task more than a few times, you have probably noticed the tax. Every session starts cold…
Joshua McDonaldMay 25, 2026EARS, Fifteen Years On: The Requirements Format Built for the Agent EraIn 2009, Alistair Mavin sat with the airworthiness regulations for a Rolls-Royce jet engine control system and found something quietly…
Joshua McDonaldMay 21, 2026MCP, PlainlyA plain explanation of what MCP changes, and why role-based access is the part that gets hard.
Joshua McDonaldMay 19, 2026Teaching Probability Through Soccer: Built With Claude CodeA statistics site for middle and high school students, built around the math pro analysts actually use.
Joshua McDonaldMay 14, 2026The Quiet Repricing of AI Coding ToolsCopilot, Cursor, Codex, and Claude Code all moved to usage-based billing inside twelve months. The driver is the same.
Joshua McDonaldMay 12, 2026Coordinating Parallel Engineering Work With ClaudeI have written before about decomposing specs against team shape, and about the specific Claude Code primitives that make the decomposition…
Joshua McDonaldMay 6, 2026Just the Road: Notes on perspective in an industry being rebuilt under our feet.My dad lives in southern Alabama near the ocean and I stay a few miles away near a beautiful community set on a golf course. I go every…
Joshua McDonaldMay 5, 2026The Little Blue Menu and What It Already Knows About AIThere’s a Chick-fil-A in College Park, Maryland, that doesn’t look like a Chick-fil-A. They painted it blue instead of red. The menu…
Joshua McDonaldApr 30, 2026Six Prompts for Reading an Engineering RoadmapWhen you need to come up to speed quickly on a project, a team, or some piece of work, you can have Claude analyze the documents and ask…
Joshua McDonaldApr 28, 2026Running a Small Team on a Big Project: Spec-Driven Development with Claude CodeMonday morning. Four engineers in the standup, a Q4 roadmap with fourteen features on it, a PM who already promised half of those to…
Joshua McDonaldApr 23, 2026I Used AI to Audit 7,200 Hospital Price Files. It Found Something the Code Missed.The story of a real data quality bug, how it got caught, and what it means for data engineering.
Joshua McDonaldApr 21, 2026The Prototype Got Cheap. The Product Didn’t.On the widening distance between a working prototype and a production system.
Joshua McDonaldApr 16, 2026A Spring Break Commute, Five Dollars, and the State of Multilingual Text-to-SpeechMost people’s mental model of AI stops at the chat window. Type a question, get an answer, move on. That framing made sense in 2023 when a…
Joshua McDonaldApr 7, 2026When You Can Build Anything, How Do You Decide What to Build?Every engineering team eventually faces this question, and fifty years of business theory offer some guidance on how to answer it.
Joshua McDonaldApr 2, 2026Spec Driven Development and Managing software projects in 2026 using AI development toolsBottom Line Up Front: AI tools now generate code faster than teams can review it, and the old process of catching mistakes in pull requests…
Joshua McDonaldMar 31, 2026Building a Local AI Coding Assistant: VS Code + Ollama + Small Language ModelsWhy Build This (And Why You Probably Shouldn’t)
Joshua McDonaldMar 26, 2026Nudge Theory Revisited: Writing Tickets for Humans and MachinesUsing ideas from behavioral economics to improve ticket writing, especially now that large language models are reading your tickets as…
Joshua McDonaldMar 23, 2026Your Team Doesn’t Need Well-Rounded Engineers. It Needs a Well-Rounded Team.Most engineering managers follow a familiar routine during performance reviews. You meet with a team member, recognize some things they do…
Joshua McDonaldMar 19, 2026Purpose Is EverythingHow to Set a North Star and Then Actually Deliver on It
Joshua McDonaldMar 17, 2026I Built a DC Transit Companion with AI on My Commute using my iPhone. Here’s what I learned.I built a DC Metro companion app called “What’s Up Metro DC” in nine days, using only my iPhone during my commute from Shady Grove to…
Joshua McDonaldMar 12, 2026The Best Engineering Leaders I’ve Seen All Have One Thing in Common: They’re Calm When Everything…There’s a moment in every engineer’s career when the pager goes off, and the world feels like it’s ending. The dashboard is a wall of red…
Joshua McDonaldMar 10, 2026How AI Dev Tools Can Turn Your Cloud Bill Into Useful InsightsYou manage a service team that owns a few services running in your organization. It’s Tuesday morning. A budget alert lands in your inbox…
Joshua McDonaldMar 4, 2026When Every Engineer Is a ManagerEvery new engineering manager experiences what I call The Backseat Driver moment. You know the feeling: someone else is driving, and you…
Joshua McDonaldMar 2, 2026n(n−1)/2Why Your Team Is Drowning in Conversation and How Math Explains Everything
Joshua McDonaldFeb 23, 2026Why Every Engineering Team Needs a Monthly Business ReviewImagine it’s the end of the quarter. Leadership is preparing the board deck, and someone asks, “What did engineering actually ship this…
Joshua McDonaldFeb 19, 2026Understanding Directed Acyclic Graphs (DAGs) with a Baseball AnalogyStop struggling with complex tech jargon, Learn what a Directed Acyclic Graph (DAG) is through the lens of a high stakes baseball play.
Joshua McDonaldFeb 16, 2026The Efficiency Illusion: Why Your AI Strategy is Accelerating Inefficiency, and How to Pivot to…Stop making your inefficiencies faster. Automating a broken workflow doesn’t create value; it just accumulates technical debt at machine…
Joshua McDonaldFeb 5, 2026Build Your Own AI General Contractor: A Practical Simulation Implementing Deterministic Guardrails…In my previous article, I explained why the time of the “Handyman AI”, one model trying to do everything, is over. I suggested that…
Joshua McDonaldJan 22, 2026Stop Hiring “Handyman” AI: Why Production Requires a General ContractorIf you want to go from basic prototypes to systems that work at scale, you need more than better prompts. You also need a new way to…
Joshua McDonaldJan 18, 2026Why Your AI Sounds Like a Corporate HR Department (And How to Fix It)Note: This is an excerpt from my new book, THE ART OF WHISPERING TO MACHINES, available now on Amazon.
Joshua McDonaldJan 17, 2026Why Your AI Feels Slow: The “Baggage Claim” Theory of LatencyWhen Houston Airport first opened, executives faced a big problem. Passengers were upset about how long they had to wait for their bags…
Joshua McDonaldJan 16, 2026How to Stop AI Hallucinations by Teaching It to Say “I Don’t Know”Your AI isn’t lying to deceive you. It’s lying to please you. Here is the engineering fix.
Joshua McDonaldJan 15, 2026Why Most AI Models Can't Count the Letter "R" in StrawberryA non-technical guide to Tokenization: why AI fails at simple math and spelling.
Joshua McDonaldJan 13, 2026Stop Treating AI Like a Brain. Treat It Like a Stadium.Why your prompts are failing and the single mental shift that fixes them.
Joshua McDonaldNov 20, 2025What a trip to the supermarket can teach you about writing security tickets that engineers actually…This is a story about connecting threads and combining ideas from different experiences, as much as it is about engineering, security, or…
Joshua McDonaldOct 16, 2025Engineering Teams in the Age of Agentic AIFor years, the default approach to building ML products that solved business problems was to establish a research-heavy organization, with…
Joshua McDonaldApr 19, 2021On testing softwareI’ve taught some college courses and have always been asked to provide a teaching philosophy as a guide to both students, but also the…
Joshua McDonaldJun 29, 2020Laid Off — What to Do When You Don’t Know What to DoPractical tips for anyone looking for work
Joshua McDonaldJan 6, 2020ComplectedI just finished reading a book that was recommended to me by a coworker. The book, titled the Unicorn Project by Gene Kim, outlines…
