Teams hit every metric—green dashboards, perfect scores. But customers were frustrated and critical incidents kept happening. Here's why: people spent more time proving they had impact than actually having it. Measurement systems don't just fail, they twist the work they measure.

Southwest Airlines lost $825 million in ten days because of a crew scheduling system from the 1990s. Pilots had warned management for years. This wasn't a technical failure—it was a leadership failure. Technical debt isn't a technical problem. It's a business problem disguised as an IT issue.

A company spent $20M on software that didn't work. They picked tools first, then tried to solve problems. After 20 years at Microsoft, I learned to ask three questions before any tech decision. Start with problems, not solutions.