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ChatGPT as a Thinking and Planning Partner

Lesson 2: Pre-Mortem Analysis and Devil’s Advocate Thinking

Lesson Objectives

By the end of this lesson, students should be able to:

  • Apply the pre-mortem technique to surface failure modes before they occur
  • Use ChatGPT as a structured devil's advocate without confirmation bias filtering
  • Respond productively to ChatGPT's challenges rather than defensively
  • Distinguish critiques worth incorporating from those that do not apply

Lesson Content

The pre-mortem technique.

"I am planning to [your plan]. Imagine it is 12 months from now and this plan has failed badly. 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."

"Without being asked to stay positive" is essential – without it, ChatGPT often balances each critique with encouragement, diluting the analytical value.

Devil's advocate.

"I believe [your position]. 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."

"Do not agree with me at the end" overrides ChatGPT's default to balanced, diplomatically framed responses. For devil's advocate to be useful, you need a genuine challenge.

Responding productively to challenge.

  • Curiosity over defensiveness: "What is true about this critique that I have not wanted to acknowledge?"
  • Distinguish applicable from inapplicable critiques: engage with the ones that reveal real weaknesses
  • Update when warranted: if a critique is compelling, change your plan

The important limitation.

ChatGPT constructs critique from general knowledge and your description – not from knowledge of your industry specifics, your team's actual capabilities, or your real market. Supplement ChatGPT's analysis with critique from people who have direct knowledge of your context.

Jamie Practice Lab

Before moving to the quiz, complete this short applied exercise:

  1. Write one realistic ChatGPT prompt that applies the main idea from Pre-Mortem Analysis and Devil's Advocate Thinking to your own work, learning, or daily life.
  2. Add one safety or verification step you would take before acting on ChatGPT's response.
  3. Revise the prompt once to include clearer context, constraints, or success criteria.

Instructor check: A strong answer should show practical use, human review, and awareness that ChatGPT output is assistance – not automatic truth or professional advice.

Added Quiz Enhancement

question_id: auto-enhancement-pre-mortem-analysis-and-devil-s-advocate-thinking-qjamie001 question_type: short_answer difficulty: applied question: Write one prompt you could use after this lesson, then name one verification or human-review step you would apply before relying on the result. correct_answer: Answers will vary; a strong answer includes a clear task, relevant context, at least one constraint or desired format, and a realistic verification or human-review step based on the stakes of the task. answer_explanation: This applied question checks whether the student can transfer the lesson into real use while maintaining responsible AI habits.

Lesson Quiz

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