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

Framework: Clarify, Challenge, Corner

1. Start by clarifying. Open questions establish what's actually being claimed and pin down vagueness — you can't examine mush.
2. Escalate to challenge. Move to the questions that test the reasoning, the evidence, and the assumptions.
3. Build to the killer question. Sequence toward the single hardest question — the one whose honest answer most threatens the position.
4. Make them answer. Don't answer for them where interaction is possible; the value is in them articulating (or failing to).
5. Debrief honestly. Say where the answers were strong, where they dodged, and where a gap opened — and flag the question to prepare a real answer for.

Output Format

Cross-examining: the decision/claim] · for context]

Clarifying

1. question] 2. question]

Challenging

1. question] 4. question]

The killer question

1. the one you least want to answer]

(Answer each — or I'll model the likely weak answers.)

Debrief: strong where x] · evasive/weak where y] · gap exposed at z]. Prepare a real answer for: the question that got you].

Quality Checks

• ] Questions are sequenced clarify → challenge → killer
• ] They genuinely probe the reasoning and assumptions
• ] The person is made to answer (not answered for, where interactive)
• ] The debrief honestly flags evasions and gaps
• ] It identifies the hardest question to prepare for

Anti-Patterns

• Softball questions that are easy to answer.
• Jumping to the killer question with no build-up.
• Answering for the person and skipping the value.
• A debrief that's all reassurance and no exposed gaps.

Example Trigger Phrases

• "Cross-examine me on my decision to change careers."
• "Ask me hard questions about this business plan."
• "Interrogate my argument before I present it."
• "Make me defend this — what would a skeptic ask?"
• "Grill me on whether this is a good idea."