Critical Path

Archive

• 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.
• 2026-05-27 Your roadmap mixes complicated problems with complex ones. Split them.
• 2026-05-26 Stop tuning prompts. Start engineering the context window.
• 2026-05-24 AI is eating the apprenticeship. Rebuild it on purpose.
• 2026-05-23 The skills you're proudest of are depreciating fastest
• 2026-05-22 Open every decision meeting with twenty minutes of silence
• 2026-05-21 Stop reorging for span of control. Reorg for cognitive load.
• 2026-05-20 Your roadmap is sitting on a map that already moved
• 2026-05-19 Stop shipping AI features. Start shipping the evals first.
• 2026-05-18 Stop reading engineering metrics like a balance sheet
• 2026-05-17 Architecture is no longer the CTO's moat. Capital allocation is.
• 2026-05-16 Stop looking for mentors. Start engineering sponsors.

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