What questions should I ask before signing an AI contract?

Executives tell me constantly that they are getting pitched AI tools every day and have no idea how to evaluate them. We see it in our own inbox. Another assistant, another automation platform, another tool promising large productivity gains. It is noise.

The biggest mistake companies make is buying tools before clearly defining the problem they are trying to solve.

Question one is the filter that eliminates most of the field. If you cannot state the problem in one sentence without using the vendor's language, you are not ready to buy anything. The test is harder than it sounds, because a good pitch supplies you with vocabulary that feels like clarity. Try describing the problem to someone in your own company who was not in the meeting.

Question two protects you a year from now. If nobody defines success before deployment, nobody can defend the investment when budgets tighten, and the initiative disappears without anyone deciding to end it. Write the number down before you sign, and make sure it is a business number rather than a usage number.

Question three is about the run, not the build. Ask for ongoing operating cost at the volume you would reach if this actually worked, because usage-based pricing means success raises your bill. Add the data preparation nobody scoped and the training that determines whether anyone adopts it.

Question four matters more than most executives realize, and it matters most in professional services. Where does your information go, who can see it, is it used to improve the vendor's product, and what happens to it if you leave? For a firm with client confidentiality obligations, that last part is not an IT question.

Question five is the one nobody asks in an enthusiastic first meeting. If this does not work in nine months, what does it cost to leave, and what do you take with you?

Do not start with the tool. Start with the assessment. Sometimes the answer is AI. Sometimes it is a simple process fix.