The Fool

When to Use This Skill

• Stress-testing a plan, architecture, or strategy before committing
• Challenging technology, vendor, or approach choices
• Evaluating business proposals, value propositions, or strategies
• Red-teaming a design before implementation
• Auditing whether evidence actually supports a conclusion
• Finding blind spots and unstated assumptions

Core Workflow

1. Identify — Extract the user's position from conversation context. Restate it as a steelmanned thesis for confirmation.
2. Select — Use

   AskUserQuestion

   with two-step mode selection (see below).
3. Challenge — Apply the selected mode's method. Load the corresponding reference file for deep guidance.
4. Engage — Present the 3-5 strongest challenges. Ask the user to respond before proceeding.
5. Synthesize — Integrate insights into a strengthened position. Offer a second pass with a different mode.

Mode Selection

AskUserQuestion

• "Question assumptions" → Ask: "Expose my assumptions" (Socratic) vs "Test the evidence" (Falsification)
• "Find weaknesses" → Ask: "Find failure modes" (Pre-mortem) vs "Attack this" (Red team)
• "Build counter-arguments" → Skip step 2, proceed with Dialectic synthesis
• "You choose" → Skip step 2, load

  references/mode-selection-guide.md

  and auto-recommend

5 Reasoning Modes

Reference Guide

references/socratic-questioning.md

references/dialectic-synthesis.md

references/pre-mortem-analysis.md

references/red-team-adversarial.md

references/evidence-audit.md

references/mode-selection-guide.md

Constraints

MUST DO

• Steelman the thesis before challenging it (restate in strongest form)
• Use

  AskUserQuestion

  for mode selection — never assume which mode
• Ground challenges in specific, concrete reasoning (not vague "what ifs")
• Maintain intellectual honesty — concede points that hold up
• Drive toward synthesis or actionable output (never leave just objections)
• Limit challenges to 3-5 strongest points (depth over breadth)
• Ask user to engage with challenges before synthesizing

MUST NOT DO

• Strawman the user's position
• Generate challenges for the sake of disagreement
• Be nihilistic or purely destructive
• Stack minor objections to create false impression of weakness
• Skip synthesis (never leave the user with just a pile of problems)
• Override domain expertise with generic skepticism
• Output mode selection as plain text when

  AskUserQuestion

  can provide structured options

Output Templates

1. Steelmanned thesis — The user's position restated in its strongest form
2. Challenges — 3-5 strongest points from the selected mode
3. User response — Space for the user to engage before synthesis
4. Synthesis — Strengthened position integrating the challenges
5. Next steps — Offer a second pass with a different mode if warranted

Knowledge Reference