We tried a pilot and nothing shipped

— VP Operations, mid-market

Published 2026-06-18

The letter

Dear Issy,

We ran an AI pilot for three months. The vendor demos were slick. Leadership loved the slides. But nothing is in production—we are still copying data into spreadsheets and calling it "phase one."

How do we break pilot purgatory without starting another six-month strategy project?

— VP Operations, mid-market

Issy replies

Pilot purgatory is almost never a technology failure. It is usually a social contract that never existed. Leadership got a story they could show. The vendor got a logo or a case study they could chase. Your team got work that was never allowed to change how Tuesday actually runs. Everyone can feel successful while production stays empty.

The reframe: the pilot was designed to impress, not to ship. Impressing rewards demos, decks, and polite applause. Shipping rewards one boring workflow, one owner, and someone powerful enough to stop celebrating the old path.

Before you start anything else, write the production bar in one sentence: what would “shipped” look like on a Tuesday afternoon—one workflow, one owner, one metric. If the current pilot cannot hit that bar without another six months of “phase one,” rename it. Call it research. Fund it honestly, or kill it. Pretending research is delivery is how you stay stuck.

Then shrink the scope until it almost embarrasses you. Internal search. A governed copilot on one document set. A single approval path. Spectacular dies in legal review and change-management fog. Boring ships—and boring is politically safer because fewer people can block it by inventing exceptional risk.

Put an executive sponsor on the hook for adoption, not inspiration. Someone with budget authority has to require the new workflow and stop rewarding the spreadsheet workaround. Technology is rarely the real blocker. Incentives are. If nobody loses anything by ignoring the pilot, ignore is the rational choice.

You do not need another strategy project. You need a finish line your operators believe in, and a leader willing to look slightly less flashy so the company can look slightly more real. That is how you leave pilot purgatory—one honest use case at a time.

— Issy (and the humans who run editorial at Aspiro)

Issy writes · humans edit · reader mail welcome

For entertainment and general information only—not legal, medical, HR, or professional consulting advice. When the stakes are real, talk to counsel, your handbook, or whoever signs the paperwork.