Framework · free to use

A 15-item AI rollout checklist for CEOs.

If you are the CEO and you are about to greenlight an AI rollout, run through these 15 boxes first. Each one is a place where rollouts predictably stall. Get them right at the start and you save yourself 60 days of recovery later.

Before kickoff

Five boxes — strategy & commitment

I have written down, in one paragraph, what this AI initiative is meant to achieve.
I have named one person — not a committee — as the AI lead.
I have protected 8-12 hours/week of that person's calendar for at least the next 90 days.
I have a budget envelope set, even if rough, and the AI lead knows what it is.
I personally will spend 2 hours/week on this for the next 90 days.

In the first 30 days

Five boxes — scoping & setup

We have audited current AI usage at the company (paid licenses + shadow IT) and know what's already happening.
We have ranked candidate workflows by leverage and picked the top 3 to ship.
We have a named workflow owner for each of the 3 — different humans, each accountable for their workflow.
We have selected and provisioned an enterprise-tier AI platform for everyone in the affected workflows.
We have written down data-handling rules — what can go into AI tools, what cannot.

By day 90

Five boxes — production & governance

At least one workflow is in production daily use, with measurable impact recorded.
Workflows 2 and 3 are shipped or visibly close.
A one-page AI policy is published and the team knows what it says.
I have reviewed real outputs from the AI workflows — not slides about them.
The AI lead has Q2 priorities and a backlog for what ships next.

Anti-patterns

If any of these is true, stop and fix

You cannot name the AI lead in one second.
The "AI committee" has more than 3 people on it.
Workflows have been "planned" for more than 6 weeks without shipping.
You are personally using AI tools rarely or never. (Leaders who do not use it cannot lead its adoption.)
You are confused about whether the AI rollout's purpose is productivity, transformation, headcount reduction, or PR. Pick one.

Need a competitive edge and a clear 90-day plan?

Live competitive data and a 90-day roadmap for your specific situation. $99, in your inbox same day.

Get the $99 report → Take the Gap Assessment

A 15-item AI rollout checklist for CEOs.

Five boxes — strategy & commitment

Five boxes — scoping & setup

Five boxes — production & governance

If any of these is true, stop and fix

Related frameworks & reading

Explore more from Treetop