Questions to ask any AI vendor
Increasingly the AI in your business won't be a chat tool at all. It'll be a feature your existing software turned on. These are the questions for that conversation.
Reviewed September 2026. This page names fast-moving vendor detail, so it carries a review date.
The nine
- Which model provider sits behind this feature, and is that in writing?
- Is our content used to train or improve any model, theirs or a third party's?
- What's retained, for how long, and what does deletion actually delete?
- Where is it processed and stored, and which jurisdictions can compel access?
- Who can review our content, under what circumstances, and is it logged?
- Can we turn the feature off per user, and does that stop processing or just hide it?
- What happens to our data if we leave, or if you're acquired?
- What does the contract say about breach notification, and on what timeline?
- Has this been assessed against the Australian Privacy Principles, and can we see it?
How to use them
Send them before the demo. A vendor whose answers are specific, written and quick has done the work. A vendor whose answers arrive as reassurance rather than detail has told you something useful too.
For regulated settings
In health, NDIS and legal work these questions sit alongside your own obligations rather than replacing them. A vendor's compliance is not your compliance, and their assessment is not yours.
Get the list
There is a printable version in resources, free, no email required.
Beyond the two we teach
Every month brings another AI product aimed at your industry, usually a wrapper around one of the big models with your sector's vocabulary on the front. Some are genuinely useful. The questions that separate them:
- Whose model is underneath, and does the answer change? If a vendor won't say, your data answer is unknowable.
- What happens to our content — the same five questions as any tier, applied to the wrapper and to the model underneath.
- Where does it sit when you stop paying? Setups, templates and history — exportable, or stranded?
- What does it do that a general tool plus a good setup doesn't? Sometimes a real answer. Often the answer is a nicer interface for something you could build in an afternoon.
- Who is accountable for a wrong output in a regulated context? Read that clause before the pricing.
The industry-specific wrapper question
A tool built for your profession can be worth paying for when it carries genuine domain structure — the forms, the codes, the report formats a regulator expects. It's worth less when the domain knowledge is a prompt you could write yourself, and you're paying a subscription for vocabulary.
The test we suggest: ask what it does that you couldn't reproduce in a setup in an hour. A confident, specific answer is a good sign. A vague one is the answer.
There's a free vendor checklist you can take into the call — no email required.
Assessing a specific tool right now? Advisory conversations often start exactly here.
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