The Executive's Guide to AI Vendor Evaluation

Tie evaluation to a specific use case

Describe the workflow, users, data, and expected outcome before comparing providers. Otherwise, the evaluation becomes a contest of features rather than a decision about business fit.

Build a test set that reflects ordinary work and difficult cases. Include incomplete inputs, ambiguous requests, and examples that should be refused or escalated. Use approved or appropriately de-identified data, not sensitive records sent casually for a trial.

Verify data and security commitments

Ask where data is processed and stored, how it is retained and deleted, whether it is used for model training, and which subprocessors participate. Confirm commitments in contracts and configuration options, not only in sales materials.

Request relevant security evidence and understand its scope and date. A report covering one service or environment does not necessarily cover the product you are buying. Check identity controls, permissions, incident notification, and logging needs.

Understand operations and model changes

Determine how the vendor communicates model updates, service changes, and known limitations. Ask whether your team can evaluate changes before they affect a production workflow, and how failures are diagnosed.

Calculate total cost at realistic volumes. Include integration, support, review, training, storage, and usage charges. Understand how output quality and service availability will be measured and what remedies the agreement actually provides.

• Test the intended workflow with representative cases.
• Confirm retention, training use, and deletion terms.
• Review security evidence for the specific service.
• Document update handling, support, costs, and exit arrangements.

Plan the exit before signing

Establish how you will export data, remove access, delete retained information, and transition the workflow. Check which configurations or integrations are portable and which must be rebuilt.

Treat selection as a recorded risk decision. Summarize the evidence, unanswered questions, compensating controls, and approval conditions so future leaders can understand why the provider was chosen.