Essays
Field-tested thinking on AI org design, AI-augmented teams, and what comes after middle management.
AI team structure: the five functions every team working with AI agents has to cover
// Structure the team around the work, not the tools: the five ORBIT functions, the coverage rule, and the three AI team structures that fail.
Will AI replace middle managers? What actually goes, and what a 50-person company should do about it
// Middle management is two jobs in one title. AI takes the routing half. Cut the layer as one headcount line and you delete both.
The AI rollout plan for a 20 to 200-person company: phases, sequence and what to do in week one
// Five phases, the tool decision last, an exit written in. The plan after the diagnosis, with a week-one checklist to run without a vendor.
AI readiness assessment for founder-led companies: 12 questions about structure, not tools
// Vendor readiness assessments measure what vendors sell. These 12 questions measure whether your org chart, handoffs and decision rights can absorb AI.
What does a Chief AI Officer do? The job description, the fractional version, and when a small company needs one
// The Chief AI Officer owns how the company gets redesigned around AI, not which tools it buys. The job, the fractional version, three signals.
Why AI Rollouts Fail: It's Your Org Chart, Not Your Tools
// Five different post-mortems, one cause. You bought a tool and kept the structure, and the structure decides whether the tool becomes how work happens or something people do on the side.
Why Your AI Training Isn't Sticking (And What to Do Instead)
// Your team passed the quiz and nobody uses the tool. That is not an education problem. You ran a curriculum against a workflow problem, in the wrong order.
The Apprenticeship Crisis: How AI Removed the Rung People Climbed
// The bottom rung was never only work. It was the training ground. Automate it and you remove the mechanism that manufactures the seniors you will be trying to hire in 2032.
The Co-Pilot Zone: Replace, Augment, or Refuse
// Every workflow in your company belongs in one of three zones. Almost nobody makes the call out loud, so everything defaults to the middle one, the only answer that requires nothing to change.
The Third Great Restructure: How Many Managers You Actually Need
// Management is two jobs sharing one title. AI is automating one and making the other harder. Cut the layer as a single budget line and you delete both.
ORBIT: The Five Functions Every AI-Augmented Team Needs (And Why Most Are Missing Two)
// Every AI-augmented team needs five functions covered: Orchestrate, Run, Build, Influence, Translate. Most are running with two or three. Here is the full framework.
The Hourglass Collapse: Why Middle Management Cannot Survive the Bottom Layer's Disappearance
// The bottom layer of white-collar work is being automated. Middle management was always load-bearing on it. Here is the org chart that comes next.