Lesson 2121 of 2244
Using AI to Sharpen Strategic Thinking and Pre-Mortems
AI as a Devil's-advocate sparring partner for plans, strategies, and decisions.
Adults & Professionals · Careers & Pathways · ~7 min read
The premise
The most underused AI mode at work is asking it to disagree with you. Used as a red-team partner, AI surfaces failure modes you missed and questions assumptions you had not noticed you were making.
What AI does well here
- Running a structured pre-mortem on a plan you are about to commit to
- Listing the strongest objections to your strategy from a named perspective
- Identifying load-bearing assumptions that, if wrong, sink the plan
- Comparing your plan against well-known reference cases or frameworks
What AI cannot do
- Replace the political and human context of how the strategy will land
- Know what your specific organization will tolerate or resist
- Predict second-order consequences in a complex system
Key terms in this lesson
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