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.

Ask for one visible outcome, not a org chart. “What will be different for customers in ninety days?” If the answer is only headcount and workshops, you have permission to stay skeptical out loud—politely.

Protect your team’s calendar. Offer a small slice of capacity for experiments with a written stop rule. Everything else stays on the roadmap you can explain to your own manager.

Find one ally in the new office who will say no to nonsense. Transformation offices fail when they only produce heat. One honest partner beats a hundred steering meetings.

You do not have to love the reorg to keep building things that work. You do have to name what “working” means before the fog becomes permanent.

— 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.