Operating Notes/Operating Note

AI Has No Go-Live Date

June 30, 2026·6 min readAndrew Cherry

Traditional software launches. AI-enabled work is cultivated. Confusing the two is the most expensive category error agencies are making right now.

Editorial summary

A working précis of the argument. The full note ships to Regesta Briefing subscribers.

Every agency leader has been trained by two decades of software rollouts to expect a go-live date. A configuration weekend, a training session, a Monday morning with a new system. AI-enabled work does not behave that way.

The first useful assistant does not replace a workflow. It sits alongside one, generating drafts a person edits, surfacing context a person confirms. Its usefulness compounds only when the workflow around it is redesigned to reward the new capability and absorb its errors.

That redesign is not a project plan. It is a practice. Which is why the agencies moving fastest right now are not the ones with the biggest AI budgets. They are the ones with a shared operating rhythm for noticing what the assistant did well, what it did poorly, and what the workflow around it should now do differently.

There is no launch date. There is only the next observation.

The agencies moving fastest do not have the biggest AI budgets. They have the shortest feedback loop between the assistant and the workflow.
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