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cross-examine-me

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Stress-test a decision or claim through a sharp, fair Q&A — the questions a good lawyer or skeptical friend would ask before you commit. Use when asked to cross-examine me, ask me hard questions about this, interrogate my plan, or make me defend this. Produces a sequenced line of probing questions (from clarifying to challenging to the killer question), space to answer, and a debrief on where your answers were strong, evasive, or exposed a gap — so weaknesses surface in private before they surface in public.

plugins/pm-thinking/skills/cross-examine-me/SKILL.md

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Nov 10, 2026
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# Cross-Examine Me

The fastest way to find the weak point in a decision is to be questioned about it by someone sharp. This runs that cross-examination: a sequence of questions that starts by clarifying, moves to challenging, and builds to the one question you least want to answer — then debriefs where you held up and where you cracked. Better to face it here than in the meeting, the pitch, or the argument.

## What This Skill Produces

- **A question sequence** — clarifying questions first, then challenging ones, building to the killer question
- **Room to answer** — it asks, you respond (interactively, or it models likely weak answers)
- **The debrief** — where your answers were solid, where they were evasive or hand-wavy, and where a real gap got exposed
- **The question to prepare for** — the one you struggled with, which others will ask too

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