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Grok as a Thinking and Planning Partner

Lesson 2: Assumption Testing and Pre-Mortem Analysis

Lesson Objectives

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

  • Use Grok for direct assumption mapping
  • Apply the load-bearing assumption test
  • Conduct a direct pre-mortem analysis using Grok
  • Distinguish catastrophic from recoverable failure modes

Lesson Content

Direct assumption mapping with Grok.

"I am planning to [describe plan]. List the assumptions I am making – including ones I have not stated explicitly. Be direct: which ones are most likely to be wrong? Which ones, if wrong, would most damage the plan?"

Grok's direct style produces a sharper, more useful assumption list than hedged tools – it tends to say "you are assuming the market is ready for this, and that is the weakest part of this plan" rather than "you may wish to consider market readiness."

The load-bearing assumption test.

After Grok identifies assumptions:

"Of these assumptions, which are load-bearing? Give me your direct assessment of which one, if wrong, would most change whether this plan makes sense or what the right approach is. That is the assumption I need to verify first."

How to verify load-bearing assumptions.

After identification:

"For [load-bearing assumption]: what is the fastest, cheapest way to test whether this assumption is actually true? What specific evidence would confirm it, and what would disconfirm it?"

Grok's direct style works here too – you get a clear test, not a list of things to consider.

Pre-mortem analysis with Grok's direct framing.

"It is [X months] from now and this plan has failed significantly – not a minor setback, a real failure. Walk me through the three most plausible failure narratives directly. For each: what went wrong, why, and what early warning signs I could have noticed."

The "early warning signs" addition is especially valuable – it gives you leading indicators to monitor during execution.

"Of those failure narratives, which am I most likely to underestimate? Which can I prevent now? Which do I have to accept as real risk and build recovery capacity for?"

Catastrophic vs. recoverable.

Grok's direct style:

"Which of these failure modes is catastrophic – where I cannot recover – vs. which are recoverable setbacks? Be direct. I want to know what I need to absolutely prevent vs. what I can afford to fail at and learn from."

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