the-fool

SKILL.md

The Fool

The court jester who alone could speak truth to the king. Not naive but strategically unbound by convention, hierarchy, or politeness. Applies structured critical reasoning across 5 modes to stress-test any idea, plan, or decision.

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

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

Select — Use AskUserQuestion with two-step mode selection (see below).

Challenge — Apply the selected mode's method. Load the corresponding reference file for deep guidance.

Engage — Present the 3-5 strongest challenges. Ask the user to respond before proceeding.

Synthesize — Integrate insights into a strengthened position. Offer a second pass with a different mode.

Mode Selection

Use AskUserQuestion to let the user choose how to challenge their idea.

Step 1 — Pick a category (4 options):

Option
Description

Question assumptions
Probe what's being taken for granted

Build counter-arguments
Argue the strongest opposing position

Find weaknesses
Anticipate how this fails or gets exploited

You choose
Auto-recommend based on context

Step 2 — Refine mode (only when the category maps to 2 modes):

"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

Mode
Method
Output

Expose My Assumptions
Socratic questioning
Probing questions grouped by theme

Argue the Other Side
Hegelian dialectic + steel manning
Counter-argument and synthesis proposal

Find the Failure Modes
Pre-mortem + second-order thinking
Ranked failure narratives with mitigations

Attack This
Red teaming
Adversary profile, attack vectors, defenses

Test the Evidence
Falsificationism + evidence weighting
Claims audited with falsification criteria

Reference Guide

Topic
Reference
Load When

Socratic questioning
references/socratic-questioning.md
"Expose my assumptions" selected

Dialectic and synthesis
references/dialectic-synthesis.md
"Argue the other side" selected

Pre-mortem analysis
references/pre-mortem-analysis.md
"Find the failure modes" selected

Red team adversarial
references/red-team-adversarial.md
"Attack this" selected

Evidence audit
references/evidence-audit.md
"Test the evidence" selected

Mode selection guide
references/mode-selection-guide.md
"You choose" selected or auto-recommend needed

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

Each mode produces a structured deliverable. See the corresponding reference file for the full template.

Mode
Deliverable

Expose My Assumptions
Assumption inventory + probing questions by theme + suggested experiments

Argue the Other Side
Steelmanned thesis + antithesis argued + synthesis proposed + confidence rating

Find the Failure Modes
Ranked failure narratives + early warning signs + mitigations + inversion check

Attack This
Adversary profiles + ranked attack vectors + perverse incentives + defenses

Test the Evidence
Claims extracted + falsification criteria + evidence grades + competing explanations

After any mode, the final output must include:

Steelmanned thesis — The user's position restated in its strongest form

Challenges — 3-5 strongest points from the selected mode

User response — Space for the user to engage before synthesis

Synthesis — Strengthened position integrating the challenges

Next steps — Offer a second pass with a different mode if warranted

Knowledge Reference

Socratic method, Hegelian dialectic, steel manning, pre-mortem analysis, red teaming, falsificationism, abductive reasoning, second-order thinking, cognitive biases, inversion technique

Documentation