How to use this checklist

Go through the five areas in order: ownership, tools and accounts, information rules, people and skills, and the first task. Write your answer next to each question. "Unclear" is a useful answer. It usually means two people would answer differently, which is a gap in itself.

This is a planning aid, not a certification, a formal audit or a score. A business with three "not yet" answers in the right places can be in better shape than one with fifteen "yes" answers on paper.

Free downloadWant the short version for your team? Get the free AI guide (PDF).

1. Ownership

Ask yourself	If the answer is not yet
Is one named person responsible for how AI is used here?	Name one. It doesn't need to be technical. It needs to be someone people will ask.
Does that person have time set aside for it this quarter?	Agree a few hours a month, or the role exists only on paper.
Do managers know what is expected of their teams?	Tell them in one paragraph: which tool, which rules, who to ask.
Do people know where to raise a problem or a mistake?	Pick one channel and say that reporting a mistake is never punished.

If nobody owns it, stop here. Rolling out a tool with no owner is how personal accounts and unapproved add-ons multiply.

2. Tools and accounts

Ask yourself	If the answer is not yet
Do you know which AI tools people use for work, including free and personal ones?	Ask, anonymously. See how to reduce AI tool sprawl.
Is there one approved tool on business accounts your organization controls?	Check what you already pay for. Microsoft 365 and Google Workspace business plans often include an AI assistant.
Do you know which AI features are switched on in the software you already use?	Ask your admin to check the admin centre for Microsoft 365 or Google Workspace, and your other main systems.
Can you see which apps are connected to work email, calendars and files?	Have your admin review connected apps. Remove any nobody can explain.

3. Information rules

Ask yourself	If the answer is not yet
Is there a written list of information that never goes into an AI tool?	Write one page. Start with the template.
Do people know what to do if they paste the wrong thing?	Add a "same day, tell this person" line to the policy.
Do you know which privacy laws and professional rules apply to the information you hold?	Ask whoever handles privacy for you. Outside Quebec, Alberta and BC, most businesses fall under PIPEDA. Clinics in Ontario also have PHIPA.
Do your client contracts say anything about AI or subcontracting?	Check your three biggest client agreements before you use AI on their work.

For the detail behind these questions, see what information should not go into AI.

4. People and skills

Ask yourself	If the answer is not yet
Have the people who will use AI practised on tasks like their own?	Access isn't skill. Plan a hands-on session, not a demo.
Do they know how to check an answer before using it?	Teach checking as a skill: facts, figures, names, anything added.
Have managers used the tool on their own work?	Managers go first. They can't coach something they haven't tried.
Is there someone people can ask the week after training?	Name a go-to person and a shared document of prompts that work.

See how to train employees to use AI for a session plan and a 30-day follow-up.

A next stepWant help reading your answers? Book a free 30-minute call, or see what the AI Readiness Assessment covers.

5. The first task

Ask yourself	If the answer is not yet
Have you picked one task that happens often and involves reading or writing?	Ask the team which part of their week is the most repetitive. Pick from that list.
Can a person check the result quickly?	Choose something easier to check. Drafts and summaries are easier than decisions.
Can you try it without sensitive information, or with information your approved tool is cleared for?	Pick a different task, or practise on fictional examples first.
Do you know roughly how long the task takes today?	Time a few normal examples now, so you can compare later.

How to read your answers

Mostly yes: pick the task from section 5, run it for 30 days, then decide whether to keep, change or stop it.
Gaps in one area: fix that area before you expand. A trained team with no information rules is a risk. Rules with no training get ignored.
Mostly unclear: the people who should agree don't. Get them in a room for an hour and go through the list together.

If most answers are not yet, do this first

Name an owner (section 1).
Choose one approved tool on business accounts, ideally one you already pay for (section 2).
Write a one-page information rule and walk the team through it (section 3).
Give people a short hands-on session on one real task (section 4).
Pick one task and run it for 30 days before adding anything else (section 5).

That order matters. Training before there's an approved tool teaches people to use personal accounts. A policy without an owner is out of date by the next software update.

Where Hero fits

You can work through this list on your own. If you'd like it done with you and written down, Hero's AI Readiness Assessment is this conversation, plus a readiness report and a written 90-day roadmap with an owner for each step, from C$1,500. If your main worry is what staff are already pasting into AI tools, start with the AI security assessment instead. Prices are on the pricing page.

AI readiness checklist for owners and managers