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Jun 12, 2026 · 7 min readRead
Technology Strategy
Executive AI readiness in five questions
The diagnostic we run with every executive team in our first thirty minutes. Honest answers reveal the right next move.
HiddenLeaf Strategy TeamMay 28, 20265 min read
Article
The five questions
1) Which two decisions in your business are worth automating? 2) Where is your data actually trustworthy today? 3) Which team owns the outcome, not the technology? 4) What is the cost of getting an answer wrong? 5) How would a competitor use AI against you in the next 18 months?
Reading the answers
Most executive teams find the exercise clarifying because the answers are usually uneven — the strategy is clear, but the data foundations are weaker than expected, or the reverse. The diagnostic surfaces the mismatch before a single dollar is committed.
What to do next
The right first move almost always involves two things: strengthening the weakest foundation on the list, and picking one high-conviction bet where AI clearly moves a needle the business already cares about.
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