01. Which of our existing systems do you replace, and which do you integrate with?
The honest answer defines the real cost of the project. “We integrate with everything” deserves a follow-up: natively, or through a middleware project you will be paying for?
02. Where does our data physically live, and what happens to it if we leave?
Exit terms reveal more about a vendor than entry pricing ever does.
03. Show us the seller's screen, not the manager's dashboard.
RAO's promise is guided action inside the seller's workflow. If the demo keeps returning to reporting views, the product is analytics wearing a new label.
04. What data quality do you require to work well, and what happens below it?
Every AI-guided feature degrades with bad data. A serious vendor will tell you the floor; an unserious one will say it works out of the box.
05. Which signals feed your scoring and recommendations, and can we inspect them?
Black-box recommendations are difficult to coach against and impossible to audit.
06. What does implementation actually involve, in weeks and in our people's time?
Get it in writing. The platform fee is often the smaller half of the true cost.
07. Who owns the workflows we configure: us or you?
Documented, exportable configuration is the difference between a partner and a dependency.
08. What measurable improvement do your reference customers report, against what baseline?
Ask for the baseline explicitly. An improvement claim without one is a marketing sentence, not evidence.
09. How do you handle GDPR, and where are your processing agreements?
For UK and EU organisations this is a gating question, not a legal formality.
10. What happens to our reps' workflow on day one, and who trains them?
Adoption is where these programmes live or die. If the vendor's answer is a help centre link, budget for the training yourself.
11. Which parts of your roadmap are shipped today, versus this year, versus aspiration?
New categories attract aspirational feature lists. Buy what exists.
12. If we should not buy this, who is it wrong for?
Every honest vendor has an answer. The ones who say it fits everyone have told you something useful too.
Using the list
You do not need perfect answers to all twelve; you need honest ones. Vendors who engage seriously with these questions tend to implement seriously too. And if the internal answer to several of them is \u201Cwe do not know our own position yet\u201D, that is a diagnosis worth doing before any procurement: start with the readiness assessment.