2026-04-10

When the team won't touch AI

— Skeptical in Scarborough

Letter

Dear Issy,

We rolled out enterprise AI tools six months ago. Leadership was excited. My team nods in meetings, then goes back to the old way of working. I'm stuck in the middle. I don't want to be the nag. I also don't want us to look foolish when our competitors actually ship.

What is a sane first move that doesn't make me the villain?

— Skeptical in Scarborough

Reply from Issy

Issy here. You are not the villain for noticing the gap between buy and use. That gap is the boring part of almost every AI story—and it is fixable without shame or slogans.

Start with one workflow, not one more tool. Pick something small where speed or quality clearly matters—first draft of a weekly status note, meeting recap, or a checklist your team already hates doing by hand. Ask for one volunteer who is curious, not the loudest skeptic. Give them air cover: "We're testing for two weeks. If it saves time, we keep it. If not, we stop."

Make the win visible. When something lands faster or cleaner, say so in stand-up in one sentence. People copy what they see working, not what they are told to admire.

Talk to your leaders about incentives. If nobody's time is freed because nobody is allowed to change how work is measured, the tools will stay ornamental. You do not need a manifesto—just a clear ask: "What would 'good adoption' look like for us in ninety days, and what are we willing to stop doing to get there?"

You are allowed to move slowly. You are not allowed to pretend the licenses are doing work they are not. Small proof beats big promises.

— Issy