Choosing documentation AI for a clinical practice comes down to six questions: who stays the author, where the data actually goes, whether the output matches your structure, what it costs at your real volume, how hard it is to leave, and what the vendor refuses to claim. Everything else in a demo is decoration.
I build one of these tools, so read this with that in mind. I've deliberately written it without naming any product, including ours, and I've included the criteria where we'd come out badly — because a buyer's guide that only contains the tests its author passes isn't a buyer's guide.

Most of what separates these tools isn't visible in a demo. It shows up in month two.
Who stays the author?
This is the first question and it's close to disqualifying. Every psychologist I've spoken to draws the same line: the clinical judgment in a document has to be theirs, and their name on it has to mean something.
So look at what the tool does at the point of judgment. Does it produce a draft you edit and sign, or does it produce conclusions? Does it ever fill in an interpretation you didn't make? Can you tell, looking at the output, which parts came from you?
The Canadian Psychological Association's guidance on artificial intelligence and psychology is worth reading before any demo, precisely because it frames the professional-responsibility side rather than the feature side. And "you review and sign" is a phrase every vendor uses, so press on what it means operationally: reviewing a draft you can actually check against the source is a different act from approving prose you'd have to re-derive.
Where does the data actually go?
Not "is it secure." Which jurisdictions, at which step, and for how long.
Ask for the path: where it's processed, where it's stored, whether any step leaves the country, what's retained, for how long, and whether anything is used to train or improve the product. Get the retention figure as a number and ask where that number is written down.
The reason this matters more than a security badge is that the obligation doesn't transfer, and it's worth reading the plain guide to what PIPEDA actually says before you take any vendor's word on this. The Office of the Privacy Commissioner states plainly that "an organization is responsible for personal information in its possession or custody, including information that has been transferred to a third party for processing." You are choosing on your own behalf, permanently.
Two specific things to be sceptical about. De-identification is a technique, not a guarantee — the privacy literature has been blunt about the limits of anonymisation, and a vendor who presents it as a guarantee is either not reading carefully or hoping you aren't. And a Canadian company is not automatically Canadian hosting — ownership, incorporation and where the servers sit are three separate claims.
If you're in Ontario, the Information and Privacy Commissioner's material on AI scribes in the health sector is the most directly relevant public document I know of, and it reads like a list of questions to bring.
Does the output match how you already work?
This is the criterion most demos are designed to obscure, and the one that decides whether the tool survives contact with your practice.
Bring your own material. Ask to run the tool against the kind of document you actually produce — your section order, your length, your phrasing — rather than the vendor's sample. Then read the output as though you were about to sign it, and count the edits.
The number that matters isn't "does it produce something." It's how long from draft to signed, compared with your current baseline. If a vendor won't let you test that with your own structure before you buy, that's an answer.

Test it on your own documents, at your own length. A vendor's sample is chosen to flatter the vendor.
What does it cost at your actual volume?
Pricing models behave very differently as volume grows. Per-seat is predictable and punishes small part-time teams. Per-document rewards low volume and gets expensive exactly when the tool is working. Per-minute makes long assessments cost more than short sessions.
Work out your real annual volume and price all the models against it, not against the headline. Then ask the questions the pricing page doesn't answer: what happens in a month where you do double, is there a minimum, what does a second reader or an administrator seat cost, and does anything change at renewal.
How hard is it to leave?
Ask on day one, not on the day you want out. Can you export your documents in a format that's useful somewhere else? Do you get the underlying content or only rendered files? How long do they keep things after you cancel, and can you get that in writing?
A vendor with a clean answer here is telling you they expect to be kept for good reasons.
What won't the vendor claim?
I've come to think this is the most diagnostic question in the whole list, and it's the one nobody asks.
Ask directly: what have you not certified? What does your tool do badly? Where would you tell me not to use it? A vendor who can answer those crisply is a vendor who knows their own product. A vendor for whom everything is a strength is describing a brochure.
Here's ours, so the question is fair. Our documentation runs on edge infrastructure in Montreal, with a single step in report drafting where content transits a large-model provider outside Canada — I'd rather write that down than let a maple leaf on a marketing page imply otherwise. And we don't name competitors, which means this guide can't tell you we beat them; it can only tell you what to measure.
Putting it together
A short, honest scorecard: authorship, data path, structural fit measured on your own documents, cost at your real volume, exit terms, and the vendor's own stated limits. Score every tool on the same six and the field usually sorts itself out quickly.
If you want to see how one of them answers, our report drafting keeps the clinician as the author who reviews and signs. But run your own six-question scorecard first — including on us. I'd rather be chosen by someone who tested than persuaded by a demo.
— Ian
