“AI readiness assessment” sounds like something that comes with a 40-page deck and a workshop where everyone gets sticky notes. It should not. A real one is closer to a home inspection: someone who builds things walks through how your business actually runs and tells you, in plain language, what is worth doing and what is not.
Here is what a good one actually looks at, and what it should cost in Canada.
1. Where the hours actually go
Not your org chart. Your Tuesdays. A real assessment starts by building an inventory of the tasks that eat your team’s week, and unlike a form you fill out, a good assessor digs for the ones nobody thinks to mention because “that is just how we do it.” Each task gets priced in hours, because that is the number every later decision hangs on. Without it, nobody can tell you what AI is worth to you.
2. What your data and tools can support
AI automation earns its keep by connecting the tools you already have, not by replacing them. So the assessment looks at where your information lives: email, spreadsheets, your CRM, your accounting software, your booking system. Can they talk to each other? Is the data clean enough to trust? A task might be a perfect automation candidate on paper and a bad first project because the data behind it is a mess. Better to know that on day one.
3. Which tasks are actually automatable
The honest split: work that follows a mostly predictable pattern is automatable, work that needs real judgment is not, and most tasks are a mix. A quote that follows your pricing rules: great candidate. A judgment call about whether to take on a difficult client: keep the human. A useful assessment sorts your whole task list into those buckets instead of promising that AI does everything. (If you want to try the sorting yourself first, our plain-English automation guide walks through it.)
4. Where the humans stay in the loop
For every candidate on the list, the report should mark where a person stays in charge: who approves what goes out, and which cases get routed to a human instead of handled automatically. This is also where privacy and compliance live, because letting software read your inbox is a decision, not a default. If an assessment never mentions human approval points, that is a seller talking, not a builder.
5. The dollars, written down
The deliverable that matters: a short written list, three to five items, each with what it costs you today in hours, what it would cost to build, and roughly when it pays for itself. Plus, just as important, the list of things to skip and why. If the report cannot say “this one is not worth it,” it is a sales document, not an assessment.
What it should cost in Canada
Honest ranges. An introductory assessment, a call plus a written list of the top opportunities, should be free or close to it; it is how a builder earns the right to quote real work. A deep version for a larger operation, with discovery sessions across billing, intake, and operations, runs as a flat fee in the low four figures. Be suspicious of open-ended “AI strategy” retainers where the deliverable is a roadmap to buy more roadmap, and of anyone charging a percentage of projected savings on numbers they made up themselves.
Three red flags
No dollar figures. If the report speaks in “transformation potential” instead of hours and dollars, you cannot act on it.
Nothing to skip. A list where every item is a “great AI opportunity” was written to sell, not to inform.
Nobody who builds. If the assessor cannot build what they recommend, the report ends where it should begin, and you get to start over with whoever actually does the work.
The plain version
A good AI readiness assessment tells you exactly where to start and in what order, in dollars, on one page you can hand to your accountant. That is the standard. Ours is the free version of exactly that: one call, one honest look at how your business runs, one written list. It is the first step of our AI automation consulting, and if the honest answer is “AI is not worth it for you yet,” the report says that too. Get your free AI audit here.
Before any assessment, put a number on it: the automation ROI calculator comes pre-loaded with the hand-built reports example from this article.
