Insights on software delivery, AI, and building tech organizations that ship.
An engineer was asked to add a retry policy to a payment call. Prompt, red. Fix it, red. Make the tests pass, green, merged. Lines read by a human: zero. The diff had the retry, a swallowed timeout, and one fewer test than that morning. Rerolling is not iteration, and volume of attempts is the cheapest signal in software.
He reads every line the machine produces and rejects most of them, fourteen times, in escalating tones. What he has never done is write down what he wanted. The Hostage Negotiator treats a tool with a spec as a colleague with feelings, and the thing being negotiated is his own uncertainty. If you cannot write the acceptance criteria, you cannot outsource the work. That was true before the machine.
Careers are expeditions, not escalators. Nobody summits alone.
Only this seriesA good engineer asked what she needed to do to make Senior, and the honest answer was that nobody had ever written it down. Most organizations do not have a career path. They have an escalator: the quiet belief that time served moves people upward on its own. Your strongest people are the ones most capable of noticing it is not real.
A résumé is a marketing document about somebody's past. A scorecard is a contract about their future: a mission, four to six measurable outcomes, and the competencies required to hit them, written before you meet a single candidate. On hiring for the climb rather than the credential, and on why unwritten standards are never neutral.
Every organization has a Dave, eleven years in, who is also the entire map. We call that tribal knowledge, which means folklore, which means we never wrote it down. On turning it into a real map of knowledge bases, areas, and topics, and on why you train the rope team rather than the climbers, because delivery failures live in the seams.
Ask why one engineer was promoted and the other was not, and you get adjectives. Ask what the second would have to do differently and you watch a competent adult discover that they cannot say. Educators solved this fifty years ago: describe mastery with verbs, order the verbs into levels, and write acceptance criteria for people the way you already do for stories.
An organization can build honest scorecards, a real knowledge map, and written behavior levels, and still lose its best people, because the whole apparatus got administered at them from a distance. Structure without care is administration. Care without structure is sentiment. Neither one gets anybody up a mountain.
Diagnosis is the easy part. This is the playbook: a six step order of operations and a 90/180/365 day roadmap, in which the org chart never appears and Step 0 is do not reorganize the titles. A written job, a written map, written expectations, and a leader who shows up. Four unglamorous things, none of which build themselves.
What has to be true before you let AI off the leash. Measure twice, prompt once.
Only this seriesEveryone bought the world's fastest power tool—generative AI—and forgot the blueprint. AI doesn't fix a broken delivery shop; it accelerates it. Meet the Magic Intern and the five foundations that must be true before you let the machine off the leash.
The most expensive thing in software is building the wrong thing efficiently. And AI is the most efficient wrong-thing-builder ever invented. Run the Program before you run the robots: humans decide what, the machine helps with how, and you distill what you learn instead of dumping it.
Two ways to be wrong about a power tool: think it's magic, or think it's possessed. Both end with no furniture. How AI actually works, why it must stay human-governed and never autonomous, and why a crew of checkable specialists beats one godlike robot.
“AI made us faster” is half a sentence; the other half has a dollar sign in it. The bill has three faces: the machine, the infrastructure, and the human review AI creates. Count all three and AI becomes a tool with a knowable cost and a knowable return.
The inspector always comes, and never at a convenient time. Build audit in, not on: every decision records itself, every claim carries its provenance, nothing is ever deleted. Then “show me the audit trail” stops ruining your Friday and becomes a query.
Diagnosis is easy; this is the playbook. A six-step order of operations and a 90/180/365-day roadmap for the AI era, where the machine shows up at Step 4 of 6. Pour the foundation before you pick up the fastest tool ever invented.
Why your technology organization is upside down, and how to flip it.
Only this seriesEvery organization has three layers: revenue drivers, builders, and support teams. Stack them wrong and gravity crushes your business. Here's how to tell if your pyramid is upside down—and what to do about it.
Every technology organization is shaped by its leader. The control vs. enable mindset, the incentive trap, and why modern organizational theory matters more than your tech stack.
Every support team optimizes for its own survival instead of delivery outcomes. Here’s how Cyber, QA, PMO, EA, and Infrastructure become disconnected silos—and what a unified foundation actually looks like.
Every audit cycle feeds the beast: new findings, new controls, more overhead, less delivery. Here’s how the flywheel works, what it actually costs, and how to break it with continuous compliance and automation.
The upside-down pyramid doesn’t just slow delivery—it drives away your best engineers, breeds Shadow IT, and hollows out the people who stay. Here’s what the dashboards miss.
The complete, practical guide to transforming your technology organization. Five steps, a full maturity assessment framework, a 90/180/365-day roadmap, and how to make the case to the board.
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