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ARTICLE · 30 OCTOBER 2025

Trick Or Treat Contracts: Avoiding AI Vendor Horror Stories

Ward and Smith, P.A
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Before adopting AI tools, businesses should follow a structured evaluation process that goes beyond feature comparisons and vendor demonstrations.

United StatesTechnology
Angela P. Doughty
Angela P. Doughty

Ed. Note: This is the fifth article in our series, "Conjuring Competitive Advantage: An AI Spellbook for Leaders," focused on unlocking AI for business with practical steps and insights. Read Part 1, Part 2, Part 3, and Part 4.

Before adopting AI tools, businesses should follow a structured evaluation process that goes beyond feature comparisons and vendor demonstrations.

AI tools can expose businesses to regulatory violations, data breaches, competitive disadvantages, and reputational damage if not properly vetted.

The AI Tool Evaluation Considerations

  1. Develop clear use cases and requirements: Understand precisely what problem you're trying to solve and whether AI is necessary or merely fashionable. Document specific functional requirements, performance expectations, and success criteria. Consider regulatory requirements and whether the proposed use creates a high-risk system under applicable AI regulations. Evaluate whether simpler, non-AI solutions

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