The Pilot Graveyard
Enterprise AI is not failing in some glamorous science-fiction way. It is failing in the most corporate way imaginable: in pilots, in procurement decks, in badly measured call-center promises, in botched integrations, and in executive fantasies about replacing human friction with software confidence. The models are often not the main problem. The problem is that companies keep deploying them into messy organizations as if a product demo were the same thing as an operating model. The result is a growing museum of avoidable fiascos, from drive-thru systems that cannot reliably hear a food order to customer-service bots that trigger rehiring, screening tools that misclassify applicants, and medical systems that look intelligent right up until the moment they become unsafe. The real story is not that AI sometimes breaks. It is that institutions keep acting shocked when a probabilistic system collides with bad data, weak governance, fantasy ROI assumptions, and a management culture addicted to shortcuts.