The "Flip the Script" Vendor Challenge: 12 Questions That Make AI Salespeople Tell the Truth

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Yesterday's Pitch Deck Decoder showed you what to look for in AI vendor presentations. Today, I'm sharing something even more powerful: the exact conversation template I use to cut through the hype and expose the reality.

I've refined these questions through hundreds of vendor evaluations. They're designed to be non-technical but impossible to dodge with prepared talking points.

Print this out before your next vendor meeting and watch what happens.

The Setup: Creating Psychological Safety for Truth

Start with: "We're excited about the potential of your solution, but to make a responsible decision, we need to understand its real capabilities and limitations. I have a few direct questions that will help us determine if this is the right fit."

This phrasing is important. It:

1. Shows you're a serious buyer

2. Creates space for honest answers

3. Frames limitations as compatibility issues, not deficiencies

The Core Questions: What They Reveal and Why They Work

1. "Walk me through your last three failed implementations – what went wrong?"

Why it works: Every solution has failed implementations. Vendors who claim otherwise are lying. Honest vendors have learned from failures and can discuss them transparently.

Red flags: "We haven't had any failed implementations" or vague references to "client issues."

Green flags: Specific examples with clear lessons learned and changes made to their approach.

Real example: A vendor candidly described a failed healthcare implementation where they discovered their model couldn't handle the complexity of medical abbreviations. They subsequently developed a medical-specific preprocessing layer. We hired them.

2. "If we had to implement a non-AI solution to solve this problem, what would you recommend?"

Why it works: Forces vendors to acknowledge simpler alternatives and reveals their understanding of the actual business problem.

Red flags: "There's no way to solve this without AI" or dismissive answers about "outdated approaches."

Green flags: A thoughtful explanation of alternatives with a clear articulation of why their AI approach provides incremental value.

Real example: An "AI-powered document processing" vendor admitted that for 70% of document types, template-based extraction would work fine. Their AI provided value only for the 30% of unstructured documents. This honesty led to a more targeted, cost-effective implementation.