Framework · free to use

Are you ready to roll out AI?

Before you sign vendor contracts or write a roadmap, run through this 25-question readiness checklist. Each "no" is either a fix-it-first item or a reason to scope smaller. None of these are technology questions — they are organization questions, which is where AI rollouts actually live or die.

Use this before you build the roadmap

Answer honestly

Score yourself 0 or 1 on each. Anything 0 needs attention before — or alongside — rollout. Total score of 18+: you are ready. 12-17: ready with caveats. Below 12: fix the foundations before scaling AI usage.

Strategy & leadership (5 questions)

Does the executive layer back this?

The CEO has stated, in writing, what AI is meant to accomplish at this company.
There is a named human (not a committee) responsible for the AI rollout.
That person has at least 8 hours per week of calendar dedicated to it.
The exec team agrees on the top 3 outcomes that matter — and they are NOT "adopt AI."
There is a budget envelope set (even if rough) for tools, training, and external help.

Operations (6 questions)

Can the company absorb new tools?

There is at least one repeatable workflow documented per major function (sales, marketing, ops).
We can name the 5 highest-leverage workflows where AI might help.
We have a way to measure outcomes (cycle time, output volume, hours saved) — even crude.
We have shipped at least one internal tool/process change in the last 12 months that the team adopted.
Our team understands what "in production" means — i.e., the difference between a demo and a daily-use tool.
We have at least one person who can write a clear prompt and refine it iteratively.

Data & security (5 questions)

Can your data go into AI tools?

We know what data classes exist in our company (public, internal, confidential, regulated).
We have written rules — even simple ones — for what data can go into external tools.
Our IT/security person knows what an enterprise AI platform's data handling looks like.
We are not currently in active remediation for a security incident.
If regulated (HIPAA, SOC 2, PCI, etc.), we know which AI platforms have the appropriate attestations or agreements.

Tools & access (4 questions)

Can people actually use the tools?

Everyone in the affected workflows can be given an enterprise AI seat without procurement gymnastics.
Our IT setup will not block paste, file upload, or browser extensions the tools require.
Our SSO supports adding new SaaS tools without a 6-week IT project.
We are willing to pay for enterprise AI tier, not just free tiers.

Culture & change (5 questions)

Will the team adopt this?

The team has been told (truthfully) that AI is meant to remove drudgery, not headcount.
Workflow owners are willing to change how they work — not just add a tool on the side.
We have a forum (Slack, regular standup, office hours) where prompts and tactics get shared.
We are willing to publish a one-page AI policy and ask people to follow it.
Senior leaders are willing to use the tools themselves — visibly — not just sponsor the work.

What to do with your score

Three readiness levels

18-25 — Ready to scale

You have the foundations. Go straight to a 90-day rollout plan with three workflows running in parallel.

12-17 — Ready with caveats

Pick one workflow, ship it well, and use the experience to build the foundations you are missing. Do not roll out everywhere yet.

Below 12 — Fix foundations first

Spend 30-60 days on the missing foundations before adding AI scope. Almost always: assign a named owner, write the data rules, and ship one small thing.

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