Copilot as a Thinking and Planning Partner By the end of this lesson, students should be able to: The pre-mortem technique. Gary Klein's pre-mortem inverts the typical planning question from "how do we succeed?" to "imagine we have failed – why did we fail?" This mental flip unlocks critiques that feel inappropriate to raise during forward-looking planning. "I am planning to [your plan]. Imagine it is 12 months from now and this plan has failed badly. We did not achieve the goal, the effort was wasted, and we have regret. Without being asked to 'stay positive,' tell me the five to seven most realistic reasons this failure might have occurred. Be specific – not generic risks, but the specific failure modes most likely given what I have told you about this plan." Why "without being asked to stay positive" matters. Without this instruction, Copilot will often balance every critique with encouragement – which dilutes the analytical value. You need the risks identified clearly, not softened. Devil's advocate: arguing the other side. When you are confident in a conclusion: "I believe [your position]. Please argue the strongest version of the opposite position. Do not agree with me at the end – I want a genuine critique of my position, not a 'but on the other hand' conclusion. Find the weakest points in my reasoning and attack them." The instruction "do not agree with me at the end" is important because Copilot defaults to balanced, acknowledging responses. For devil's advocate to be useful, you need a genuine challenge, not a diplomatically framed echo. Responding productively to challenge. The value of pre-mortem and devil's advocate analysis depends entirely on how you respond: The important limitation. Copilot constructs critique from general knowledge and your description of the plan – not from knowledge of your industry specifics, your team's actual capabilities, or your real market. The most important risk in your plan might be one Copilot cannot surface because it requires context you have not shared. Supplement Copilot's analysis with critique from people who have direct knowledge of your context. A nonprofit director is confident in a new fundraising strategy. She runs a pre-mortem: Copilot generates seven failure modes. Six she has anticipated. The seventh – that the strategy depends on maintaining a specific corporate donor relationship, and she has not yet re-confirmed that relationship for the next year – she has not thought about. She adds a "confirm primary donor relationship" action to her Q1 priorities. The entire value of the pre-mortem came from that one finding. Log in and enroll to access lesson quizzes.
Lesson 2: Pre-Mortem Analysis and Devil’s Advocate Thinking
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Practical Example