Kuber Sharma.

The Pilot Trap: the five-stage model for why enterprise AI pilots die before production

Note on the name: "The Pilot Trap" is also the title of a 2026 book by Vijayan Seenisamy. The five-stage model on this page is a separate framework and is not affiliated with that book.

Fig. 01: Lifecycle of a doomed pilot Time →

An executive returns from a conference. Budget appears with unusual ease; the room is warm.

Enthusiasm meets the org chart. A use case is chosen for visibility, rarely for value.

The trap. Sandbox success is mistaken for product readiness; production debt accrues unobserved.

A question arrives from legal, security, or the system-of-record team. Meetings move to fortnightly.

The pilot is not cancelled. It is omitted from the next planning cycle. Weights sit on a disk.

The trap springs at Sandboxing: when the pilot works beautifully and nobody has told IT security, procurement, or legal that it exists. The pull quote
The antidote

Put IT security, procurement, and legal in the room at Scoping.

The fastest way to reach me is [email protected]. I read it. I write back, eventually.

© 2026 Kuber Sharma · All writing my own Set in Newsreader, Inter & JetBrains Mono · Made in Seattle