Free Guide
The 5 Questions That Separate Smart AI Investments from Expensive Mistakes
A free guide for executives evaluating AI — from someone who's watched billions get spent on both.
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Most AI investments fail before the contract is signed.
Not because the technology doesn't work. Because nobody asked the right questions.
87% of AI pilots never reach production. The ones that do almost always share one thing: someone asked hard questions early.
5 questions. 10 minutes.
A completely different approach to AI investment.
What specific task does this replace or improve?
Why most AI projects fail the "Monday morning test" — and the 2-sentence reframe that fixes it.
What does it get wrong, and what happens when it does?
The accuracy math that changes decisions: why "95% accurate" can mean $2.6M/year in error costs.
What's the total cost — not the vendor quote?
The 5-layer cost stack and the 2.5-3x multiplier rule. With a real example: $380K quote → $1.1M actual.
How do we measure success in 90 days?
Good metrics vs. bad metrics, and why "improved efficiency" gets you fired while "reduced processing time from 4 hours to 30 minutes" gets you funded.
What's our exit plan if this doesn't work?
The 3 lock-in traps and 5 contract clauses that protect you — because after signing, your leverage is gone.
From someone who's been in the room.
Vance Sterling has spent 20 years in banking technology — leading AI implementations from proof-of-concept to production at institutions managing billions in assets. He's seen what a $380K vendor quote actually costs ($1.1M). He's watched a 47-page AI proposal die in committee while a one-page brief got approved in a single meeting.
Stop evaluating AI with your gut.
Start with 5 questions.
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