COLLECTED & CONSIDERED
Collected & Considered
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Cover of The AI-Driven Leader

The AI-Driven Leader

by Geoff Woods

Leadership, Business & Money

Added to the collectionJuly 19, 2026

Selected Passages

Selected passages

Instead of just asking AI questions, turn the tables and have it ask you the right questions.

AI won’t replace you; those who harness AI will replace those who don’t.

To unlock AI as your Thought Partner, ask it to interview you to gather all the necessary information and then complete a task. One pro tip: make sure to tell it to ask you one question at a time. Otherwise, it may overwhelm you with several questions at once.

My favorite prompt recipe for strategic thinking is CRIT™: Context - Role - Interview - Task.

AI can help you weigh the opportunity cost by asking you, “If you focus on this, what will you have to say no to?”

“Standards without consequences are merely suggestions.” —Gene Rivers

Once you are happy with the result, do not stop there. Ask AI to switch roles: Now I want you to act as the Challenger. You are world-class at stress testing the insufficiency of a plan. Tell me what you like about this, what you don’t like, and the top changes I would need to make to ensure this plan is bulletproof.