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Your AI Vendor Is Hoping You Don’t Ask About Security

I’ve sat in a lot of vendor demos. The slides are beautiful, the demo runs flawlessly, and nobody says a word about where your data goes or who can read it. That silence isn’t an accident, it’s the strategy. Here are the five AI vendor security questions the industry hopes you’ll skip, why they matter more for small businesses than enterprises, and how to tell a serious vendor from one who bolted AI onto a weak foundation.
Short Excerpt (150 chars): Most AI vendors bet you won’t ask about security. The 5 questions to ask before you sign and how to tell a serious vendor from a risky one.

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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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