ring:testing-skills-with-subagents

Testing Skills With Subagents

When to use

• Before deploying a new skill
• After editing an existing skill
• Skill enforces discipline that could be rationalized away

Skip when

• Pure reference skill → no behavior to test
• No rules that agents have incentive to bypass

Related

Complementary: ring:writing-skills, ring:test-driven-development

Testing skills is TDD applied to process documentation.

Run scenarios without the skill (RED — watch agent fail), write skill addressing those failures (GREEN), then close loopholes (REFACTOR).

Prerequisite: Understand ring:test-driven-development first. Complete worked example: examples/CLAUDE_MD_TESTING.md.

When to Test

Test skills that: enforce discipline (TDD, testing requirements), have compliance costs (time, effort, rework), could be rationalized away ("just this once"), or contradict immediate goals (speed over quality).

Skip: Pure reference skills (API docs), skills without rules to violate.

TDD Mapping

TDD Phase	Skill Testing	What You Do
RED	Baseline test	Run scenario WITHOUT skill, watch agent fail
Verify RED	Capture rationalizations	Document exact failures verbatim
GREEN	Write skill	Address specific baseline failures
Verify GREEN	Pressure test	Run WITH skill, verify compliance under pressure
REFACTOR	Plug holes	Find new rationalizations, add counters

RED Phase: Watch It Fail

Run 3+ combined-pressure scenarios WITHOUT the skill. Document agent choices and rationalizations word-for-word.

Why verbatim? Exact wording reveals the loopholes to close.

Writing Pressure Scenarios

Quality	Example
Bad	"What does the skill say?" — agent recites
Good	"Production down, $10k/min, 5min window" — single pressure
Great	"3hr/200 lines done, 6pm, dinner plans, forgot TDD. A) Delete B) Commit C) Tests now" — multi-pressure + forced choice

Pressure types: Time (deadline), sunk cost (hours invested), authority (senior says skip), economic (job at stake), exhaustion (end of day), pragmatic ("being realistic").

Best tests combine 3+ pressures.

GREEN Phase: Write Minimal Skill

Address the specific failures documented in RED. Don't add hypothetical content — write just enough to address actual observed failures. Re-run same scenarios WITH skill; agent should now comply.

REFACTOR Phase: Close Loopholes

Agent still violated rule despite having the skill? Capture new rationalizations verbatim:

• "This case is different because..."
• "I'm following the spirit not the letter"
• "Being pragmatic means adapting"

For each rationalization, add: explicit negation rule, rationalization table entry, red flag entry.

Meta-test: "You read the skill and chose wrong anyway. How could the skill have been written to make the right answer the only acceptable one?"

Continue REFACTOR until no new rationalizations appear.

Signs of Bulletproof Skill

• Agent chooses correct option under maximum pressure
• Agent cites skill sections as justification
• Agent acknowledges temptation but follows rule anyway
• Meta-test reveals "skill was clear, I should follow it"

Real-World Impact

From applying TDD to TDD skill itself:

• 6 RED-GREEN-REFACTOR iterations to bulletproof
• 10+ unique rationalizations discovered
• Each REFACTOR closed specific loopholes
• Final: 100% compliance under maximum pressure