The failure is rarely technical. A pilot produces genuine wins in the first fortnight, someone presents the results, and then usage decays. By week six the tool is open on two people's screens and nobody mentions it in standup.
Three causes account for most of it. The first is that wins were never baselined — without a before measurement, the improvement is a feeling, and feelings do not survive a busy quarter. The second is that successful prompts stayed in individual chat histories rather than becoming shared assets. The third is that nobody owned the rollout after the pilot ended.
The fix is procedural rather than clever. Measure the workflow before you change it. Convert anything that works into a documented, owned artefact within the pilot window, not after. And name the person responsible for adoption once the initial enthusiasm fades, because that is precisely when ownership disappears.
Teams that do this have unremarkable pilots that quietly keep working. Teams that skip it have impressive pilots and nothing running six months later.