Archive • Critical Path • Buttondown

Archive

2026-10-09 Stop asking when it ships. Track the decisions that block it.
2026-10-08 A reorg is a communication plan with an org chart attached
2026-10-07 Most programs run one diamond. That's why they ship the wrong thing.
2026-10-06 Your AI bill has no owner. Name one before the invoice does.
2026-10-05 AI broke your delivery dashboard. Measure the review queue instead.
2026-10-04 The connective-tissue job is ending. Become the judgment layer.
2026-10-03 Your Staff archetype is a season, not a title
2026-10-02 Every meeting should close a decision. Cancel the ones that can't.
2026-10-01 Flattening didn't kill middle management. It made it a polarity.
2026-09-30 Your plan assumes the problem is merely complicated. Check first.
2026-09-29 Your agents don't need a manager. They need a delegation board.
2026-06-11 Stop chasing "influence without authority." Design decision rights instead.
2026-06-10 Diagnose the program with Cynefin before you write a single milestone
2026-06-09 If you can't write the eval, you can't ship the AI feature
2026-06-08 Stop reporting DORA. Start interpreting it.
2026-06-07 Treat agents as headcount, or watch your org chart break
2026-06-02 AI features fail at the handoff, not the model.
2026-06-01 Every AI throughput metric needs an instability twin
2026-05-31 Stop measuring scope in headcount. Start measuring it in decisions per week.
2026-05-28 Let AI do the cheap glue work. Defend the expensive kind.