The Question Nobody Asks Their AI Vendor

In every AI vendor evaluation, teams ask what the tool does, what it costs, and how fast it deploys. Almost nobody asks the question that matters most on the worst day: when we leave, how do we get our data out, and what happens to what's left behind?

Ask it now, while everyone is friendly. Can we export our data in a usable format, or only as PDFs designed to be unreadable? How long does export take for an account our size? After we leave, is our data deleted — and does "deleted" include backups, logs, and training pipelines? Get the answers in the contract, not in a sales call.

Vendors who have good answers will give them proudly. Data portability is a sign of a mature product. Vendors who squirm are telling you something important about how they view your data: as theirs.

I watched this exact dynamic in systems work years ago, with databases far less glamorous than AI. The organizations that negotiated their exit on day one left cleanly. The ones that didn't paid for the lesson in migration fees and lost history.

Ask the uncomfortable question early. It's only uncomfortable once.

I explain frameworks; I don't give legal counsel.