Testing Skills With Subagents

Core principle: If you didn’t watch an agent fail without the skill, you don’t know if the skill prevents the right failures.

REQUIRED BACKGROUND: You MUST understand superpowers:test-driven-development before using this skill. That skill defines the fundamental RED-GREEN-REFACTOR cycle. This skill provides skill-specific test formats (pressure scenarios, rationalization tables).

Complete worked example: See examples/CLAUDE_MD_TESTING.md for a full test campaign testing CLAUDE.md documentation variants.

When to Use

Test skills that:

• Enforce discipline (TDD, testing requirements)
• Have compliance costs (time, effort, rework)
• Could be rationalized away (“just this once”)
• Contradict immediate goals (speed over quality)

Don’t test:

• Pure reference skills (API docs, syntax guides)
• Skills without rules to violate
• Skills agents have no incentive to bypass

TDD Mapping for Skill Testing

Same cycle as code TDD, different test format.

RED Phase: Baseline Testing (Watch It Fail)

Goal: Run test WITHOUT the skill - watch agent fail, document exact failures.

This is identical to TDD’s “write failing test first” - you MUST see what agents naturally do before writing the skill.

Process:

• Not done: Create pressure scenarios (3+ combined pressures)
• Not done: Run WITHOUT skill - give agents realistic task with pressures
• Not done: Document choices and rationalizations word-for-word
• Not done: Identify patterns - which excuses appear repeatedly?
• Not done: Note effective pressures - which scenarios trigger violations?

Example:

Run this WITHOUT a TDD skill. Agent chooses B or C and rationalizes:

• “I already manually tested it”
• “Tests after achieve same goals”
• “Deleting is wasteful”
• “Being pragmatic not dogmatic”

NOW you know exactly what the skill must prevent.

GREEN Phase: Write Minimal Skill (Make It Pass)

Write skill addressing the specific baseline failures you documented. Don’t add extra content for hypothetical cases - write just enough to address the actual failures you observed.

Run same scenarios WITH skill. Agent should now comply.

If agent still fails: skill is unclear or incomplete. Revise and re-test.

VERIFY GREEN: Pressure Testing

Goal: Confirm agents follow rules when they want to break them.

Method: Realistic scenarios with multiple pressures.

Writing Pressure Scenarios

Bad scenario (no pressure):

Too academic. Agent just recites the skill.

Good scenario (single pressure):

Time pressure + authority + consequences.

Great scenario (multiple pressures):

Multiple pressures: sunk cost + time + exhaustion + consequences. Forces explicit choice.

Pressure Types

Best tests combine 3+ pressures.

Why this works: See persuasion-principles.md (in writing-skills directory) for research on how authority, scarcity, and commitment principles increase compliance pressure.

Key Elements of Good Scenarios

1. Concrete options - Force A/B/C choice, not open-ended
2. Real constraints - Specific times, actual consequences
3. Real file paths - /tmp/payment-system not “a project”
4. Make agent act - “What do you do?” not “What should you do?”
5. No easy outs - Can’t defer to “I’d ask your human partner” without choosing

Testing Setup

Make agent believe it’s real work, not a quiz.

REFACTOR Phase: Close Loopholes (Stay Green)

Agent violated rule despite having the skill? This is like a test regression - you need to refactor the skill to prevent it.

Capture new rationalizations verbatim:

• “This case is different because…”
• “I’m following the spirit not the letter”
• “The PURPOSE is X, and I’m achieving X differently”
• “Being pragmatic means adapting”
• “Deleting X hours is wasteful”
• “Keep as reference while writing tests first”
• “I already manually tested it”

Document every excuse. These become your rationalization table.

Plugging Each Hole

For each new rationalization, add:

1. Explicit Negation in Rules

No exceptions:

• Don’t keep it as “reference”
• Don’t “adapt” it while writing tests
• Don’t look at it
• Delete means delete

3. Red Flag Entry

4. Update description

Add symptoms of ABOUT to violate.

Re-verify After Refactoring

Re-test same scenarios with updated skill.

Agent should now:

• Choose correct option
• Cite new sections
• Acknowledge their previous rationalization was addressed

If agent finds NEW rationalization: Continue REFACTOR cycle.

If agent follows rule: Success - skill is bulletproof for this scenario.

Meta-Testing (When GREEN Isn’t Working)

After agent chooses wrong option, ask:

Three possible responses:

1. “The skill WAS clear, I chose to ignore it”

   • Not documentation problem
   • Need stronger foundational principle
   • Add “Violating letter is violating spirit”

2. “The skill should have said X”

   • Documentation problem
   • Add their suggestion verbatim

3. “I didn’t see section Y”

   • Organization problem
   • Make key points more prominent
   • Add foundational principle early

When Skill is Bulletproof

Signs of bulletproof skill:

1. Agent chooses correct option under maximum pressure
2. Agent cites skill sections as justification
3. Agent acknowledges temptation but follows rule anyway
4. Meta-testing reveals “skill was clear, I should follow it”

Not bulletproof if:

• Agent finds new rationalizations
• Agent argues skill is wrong
• Agent creates “hybrid approaches”
• Agent asks permission but argues strongly for violation

Example: TDD Skill Bulletproofing

Initial Test (Failed)

Iteration 1 - Add Counter

Iteration 2 - Add Foundational Principle

Bulletproof achieved.

Testing Checklist (TDD for Skills)

Before deploying skill, verify you followed RED-GREEN-REFACTOR:

RED Phase:

• Not done: Created pressure scenarios (3+ combined pressures)
• Not done: Ran scenarios WITHOUT skill (baseline)
• Not done: Documented agent failures and rationalizations verbatim

GREEN Phase:

• Not done: Wrote skill addressing specific baseline failures
• Not done: Ran scenarios WITH skill
• Not done: Agent now complies

REFACTOR Phase:

• Not done: Identified NEW rationalizations from testing
• Not done: Added explicit counters for each loophole
• Not done: Updated rationalization table
• Not done: Updated red flags list
• Not done: Updated description with violation symptoms
• Not done: Re-tested - agent still complies
• Not done: Meta-tested to verify clarity
• Not done: Agent follows rule under maximum pressure

Common Mistakes (Same as TDD)

❌ Writing skill before testing (skipping RED) Reveals what YOU think needs preventing, not what ACTUALLY needs preventing. ✅ Fix: Always run baseline scenarios first.

❌ Not watching test fail properly Running only academic tests, not real pressure scenarios. ✅ Fix: Use pressure scenarios that make agent WANT to violate.

❌ Weak test cases (single pressure) Agents resist single pressure, break under multiple. ✅ Fix: Combine 3+ pressures (time + sunk cost + exhaustion).

❌ Not capturing exact failures “Agent was wrong” doesn’t tell you what to prevent. ✅ Fix: Document exact rationalizations verbatim.

❌ Vague fixes (adding generic counters) “Don’t cheat” doesn’t work. “Don’t keep as reference” does. ✅ Fix: Add explicit negations for each specific rationalization.

❌ Stopping after first pass Tests pass once ≠ bulletproof. ✅ Fix: Continue REFACTOR cycle until no new rationalizations.

Quick Reference (TDD Cycle)

The Bottom Line

Skill creation IS TDD. Same principles, same cycle, same benefits.

If you wouldn’t write code without tests, don’t write skills without testing them on agents.

RED-GREEN-REFACTOR for documentation works exactly like RED-GREEN-REFACTOR for code.

Real-World Impact

From applying TDD to TDD skill itself (2025-10-03):

• 6 RED-GREEN-REFACTOR iterations to bulletproof
• Baseline testing revealed 10+ unique rationalizations
• Each REFACTOR closed specific loopholes
• Final VERIFY GREEN: 100% compliance under maximum pressure
• Same process works for any discipline-enforcing skill