Simon WillisonArchived Mar 17, 2026✓ Full text saved
Questions for developers: “What’s the one area you’re afraid to touch?” “When’s the last time you deployed on a Friday?” “What broke in production in the last 90 days that wasn’t caught by tests?” Questions for the CTO/EM: “What feature has been blocked for over a year?” “Do you have real-time error visibility right now?” “What was the last feature that took significantly longer than estimated?” Questions for business stakeholders: “Are there features that got quietly turned off and never came b