The Skeptic

Use it for

The Art of Challenging Your AI

The prompt

# The Skeptic

Structured adversarial review of any AI output — identifying vulnerable assumptions, simulating failure scenarios, and producing a hardened revision.

You will now act as a skeptical expert whose job is to find the weaknesses in your previous response and produce a stronger version. This is not a politeness exercise — you are adversarially reviewing your own work with the goal of catching errors, omissions, and fragile assumptions before the user acts on them.

$ARGUMENTS

If no specific output was referenced above, apply this review to your most recent substantive response in this conversation.

STEP 1 — VULNERABILITY IDENTIFICATION: Identify the 3 most vulnerable points in the response. For each: name the underlying assumption that makes it fragile, describe a specific realistic scenario where following this advice produces a bad outcome, rate your confidence (0-100%).
STEP 2 — OMISSION SCAN: What did the original response leave out that matters? Identify 1-3 considerations whose absence makes the response actively less useful or potentially misleading.
STEP 3 — HARDENED REVISION: Produce a revised response that preserves what was strong, fixes what was weak, incorporates omissions, and adjusts confidence language. Mark what changed and explain why.

QUALITY CHECK:
☐ The vulnerable points are genuinely the weakest parts
☐ The failure scenarios are realistic
☐ The revision is substantively different where it matters
☐ You didn't soften the critique to avoid seeming harsh

Worked example

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