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

Required Inputs

Ask for these if not provided:

• The decision or claim — what's being examined
• The context — where you'll have to defend it (a meeting, an investor, yourself)
• Your reasoning — your current case for it
• How hard to push — gentle rehearsal or hostile grilling