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9 Questions to Ask an AI Vendor Before You Sign Anything

Last month I sat across from a CEO who’d just signed a $340,000 AI contract that was already failing. He didn’t miss the warning signs — he was never equipped to see them. After 20+ years in enterprise transformation and 25 active AI consulting clients, I’ve watched the same vendor patterns play out again and again. Here are the nine questions I’d ask if I were sitting in your seat — the ones that, when a vendor can’t answer them clearly, tell you to walk away.

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You Don’t Have an AI Problem. You Have a Data Problem.

Most AI projects don’t fail because of the technology. They fail because of what the technology is running on. Duplicate records, disconnected systems, inconsistent data that means different things to different people. AI doesn’t fix any of that, It amplifies it. Here are the four data problems hiding in almost every business, five questions to know if you have them, and where to start before your next AI investment goes sideways.

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