Sleepless over an AI reorg

— Sleepless in Seattle

Published 2026-04-22

The letter

Dear Issy,

Our company just created an “AI transformation office” overnight. Six people with new titles, a deck full of arrows, and a mandate to “accelerate AI across the enterprise.” My team builds the products. Now we report to someone who used to run sales enablement.

I’m not against change. I’m against fog. How do I stay useful without letting my team get absorbed into slide theater?

— Sleepless in Seattle

Issy replies

Fog is exhausting because it asks you to perform certainty you do not have. Your insomnia is data, not weakness. An overnight “AI transformation office” with new titles, arrows on a deck, and a mandate to accelerate everything is a political event first. Someone needed a structure they could point to. Your team still has to ship products. Reporting to a former sales-enablement leader does not make the mandate wrong—but it does explain why the fog feels thick.

Ask for one visible outcome, not another org chart. “What will be different for customers in ninety days?” If the answer is only headcount and workshops, you have permission to stay politely skeptical. Skepticism is not disloyalty when you are paid to build things that work.

Protect your team’s calendar. Offer a small, written slice of capacity for experiments with an explicit stop rule. Everything else stays on the roadmap you can defend to your own manager. Transformation offices fill their calendars with other people’s people. You do not have to feed that hunger with your entire roadmap.

Find one ally in the new office who will say no to nonsense. Offices like this fail when they only produce heat—steering meetings, status templates, and language nobody believes. One honest partner who respects delivery beats a hundred slides that redraw accountability without changing it.

You do not have to love the reorg to keep building. You do have to name what “working” means before fog becomes the permanent culture. Ask for clarity in public. Protect craft in private. Stay useful without becoming a prop in someone else’s theater.

— 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.