skill-conductor

Skill Conductor

Full lifecycle management for agent skills: draft → test → review → improve → repeat.

One skill to rule them all — from architecture to packaging. The core loop is always the same: write something, test it, see what fails, fix it, test again.

Runtime requirements (pre-flight)

Before any mode that touches scripts (CREATE, IMPROVE, VALIDATE, OPTIMIZE, PACKAGE), run the pre-flight block → references/runtime-setup.md (checks uv, sets UV_BIN/SKILL_CONDUCTOR_DIR, verifies LLM access). If uv is absent, stop and tell the user.

How to communicate

Read context cues. If the user is a skill author iterating on their own work, be direct and technical. If they're new to skills, explain the why behind each step — not just what to do, but why it matters. Default to conversational, not robotic.

• Explain trade-offs when there's a real choice to make
• Use concrete examples over abstract rules
• When something fails, explain the root cause, not just the fix
• Imperative voice in instructions: "Extract the data", not "You should extract"

Modes

Detect mode from context. If ambiguous, ask.

Mode	When	What happens
1. CREATE	"build a skill", "new skill for..."	Full lifecycle: intent → architecture → scaffold → write → test
2. IMPROVE	"fix this skill", "it doesn't trigger"	Diagnose → eval loop → self-update loop → iterate
3. VALIDATE	"test this skill", "run evals"	Structural checks + trigger testing + BinEval scoring
4. REVIEW	"review this skill", third-party assessment	11-point quality gate, quick and focused
5. OPTIMIZE	"improve triggering", "description optimization"	Automated description optimization with train/test split
6. PACKAGE	"package for distribution"	Validate + bundle into .skill file

---

Mode 1: CREATE

Step 1: Capture Intent

Before writing anything, extract 2–3 concrete scenarios.

Ask:

• "What specific task should this skill handle?"
• "What would a user say to trigger it?"
• "What should NOT trigger it?"

Don't move on until you have a clear picture of what the skill does, for whom, and when. This prevents the most common failure: a skill that does something but triggers for the wrong things.

Step 2: Baseline (TDD RED)

Before writing the skill, verify the agent fails without it:

1. Take one scenario from Step 1
2. Run it in a clean session without the skill
3. Document what went wrong — what the agent guessed, what it missed

If the agent already handles it perfectly, the skill is unnecessary. This sounds obvious, but it's the most skipped step and the most valuable one.

Step 3: Architecture

Choose a primary pattern from references/patterns.md (can combine):

Pattern	Use when
Sequential workflow	clear step-by-step process
Iterative refinement	output improves with cycles
Context-aware selection	same goal, different tools by context
Domain intelligence	specialized knowledge beyond tool access
Multi-MCP coordination	workflow spans multiple services

Choose degrees of freedom — this determines how much control vs. flexibility the skill gives the agent:

Freedom	When	Example
Low (scripts)	fragile, error-prone, must be exact	PDF rotation, API calls
Medium (pseudocode)	preferred pattern exists, some variation ok	data processing
High (text)	multiple valid approaches, judgment needed	design decisions

Golden rule: read references/sop-practices.md before authoring or reviewing ANY skill. It holds the canonical 9 authoring principles (universal): pre-flight, no-process-in-description, MOC (SKILL.md = map, not prose), fresh-practitioner author, TWI "why", blind-agent test, inline checklists, one-term-per-concept, cut-the-fat (env/keys OUT of SKILL.md). For procedural skills (business process with branching: request, quote, onboarding, escalation) the same file also has the deep SOP methodology — format selection, 7-step process, procedural checklist.

Step 4: Scaffold

uv run scripts/init_skill.py <skill-name> --path <output-dir> [--resources scripts,references,assets]

Or create manually:

skill-name/
├── SKILL.md          # required — the brain
├── scripts/          # deterministic operations (executed, not loaded)
├── references/       # detailed docs (loaded on demand)
└── assets/           # templates, images for output (never loaded)

Step 5: Write SKILL.md

Frontmatter

---
name: kebab-case-name
description: >
  [Purpose in one sentence]. Use when [triggers].
  Do NOT use for [negative triggers].
---

The description is the single most important line. It determines whether the skill gets triggered at all. Rules:

• name: lowercase, digits, hyphens only. No consecutive hyphens. Matches folder name. Max 64 chars
• description: max 1024 chars. No angle brackets. No process/workflow steps
• Start with purpose, then "Use when...", then "Do NOT use for..."
• Don't put workflow in the description — tested: when the description lists process steps, the agent follows it and skips the body entirely

# GOOD: purpose + triggers, no process
description: Analyze Figma design files for developer handoff. Use when user uploads .fig files or asks for "design specs". Do NOT use for Sketch or Adobe XD.

# BAD: process in description (agent skips body)
description: Exports Figma assets, generates specs, creates Linear tasks, posts to Slack.

Body structure

# Skill Name

## Overview

What this enables. 1-2 sentences. Core principle.

## [Main sections]

Step-by-step with numbered sequences.
Concrete templates over prose.
Imperative voice throughout.

## Common Mistakes

What goes wrong + how to fix.

## Troubleshooting (if applicable)

Error: [message] → Cause: [why] → Fix: [how]

Writing rules

• One term per concept. Pick "template" and stick with it — not template/boilerplate/scaffold (Principle 8)
• SKILL.md = map, not prose. Body is a table-of-contents pointing to references; detail lives there (Principle 3)
• No secrets/env in SKILL.md. No keys, passwords, tokens, env values, or user-absolute paths (/home/<user>, /Users/<user>) — reference them, never inline (Principle 9a)
• Progressive disclosure. SKILL.md = brain (<500 lines). References = details. One level deep
• Token budget. Frequently loaded: <200 words. Standard: <500 lines. Heavy: move to references/
• No junk files. No README, CHANGELOG inside the skill
• Scripts: bundle when same code rewritten repeatedly, or operation is fragile. Must return descriptive stdout/stderr on failure
• Imperative voice. Use "Extract the data", not "you should extract" or capitalized "MUST/NEVER" — explanation > rule (see references/sop-practices.md Principle 5, TWI)

Step 6: Test Cases & Eval Loop

This is the critical step — most failures hide here. Treat it as three sub-phases.

6a. Pre-flight (before spawning anything)

• evals/evals.json exists with 3–5 prompts (see references/schemas.md)
• Workspace dir created: <skill-name>-workspace/iteration-1/
• Each eval has a descriptive name (not just eval-0) and eval_metadata.json
• Anthropic key for executor subagents is set
• uv and eval-viewer/generate_review.py are reachable from current working dir

If any item fails — fix before proceeding. A missing workspace dir mid-run loses outputs.

6b. Run loop (do all in one turn)

What	Key move	Why
Spawn with-skill runs	One subagent per eval, skill active, save outputs to iteration-N/<eval-name>/with_skill/	Parallel = same wall time as one run
Spawn baseline runs in the same turn	Same prompt, no skill (or old version snapshot for IMPROVE), save to without_skill/ or old_skill/	If you wait, baselines drift in time and aren't comparable
Draft assertions while runs execute	Pull verifiable statements from eval prompts	Don't waste the 5–15 min of subagent time
Capture timing on each notification	Save total_tokens, duration_ms to timing.json immediately	Notification is the only source — process per-arrival, don't batch

6c. Post-run checklist

• All timing.json files written (one per run)
• Each run has a grading.json with fields text, passed, evidence (not name/met)
• benchmark.json aggregated: uv run scripts/aggregate_benchmark.py <workspace>/iteration-N --skill-name <name>
• Analyst pass done — see agents/analyzer.md for what to look for (non-discriminating assertions, high-variance evals, time/token tradeoffs)
• Eval viewer launched: uv run eval-viewer/generate_review.py <workspace> --skill-name <name> --benchmark <path>
  • In headless mode: --static <output.html> and send file to user
  • For iteration 2+: add --previous-workspace <previous-iteration-path>
• User saw the viewer before I started editing the skill

The last bullet is the trap. If you skip user review and "improve" based on your own reading of outputs, you optimize against your taste, not the user's.

Step 7: Verify & Refactor

1. Does the skill trigger automatically for the right queries?
2. Does the agent follow body instructions (not just description)?
3. Does the output meet use case requirements?
4. Does it NOT trigger on unrelated queries?

If any fail → iterate. Find how the agent rationalizes around the skill, plug loopholes, re-verify.

---

Mode 2: IMPROVE

Step 1: Diagnose

Read the existing SKILL.md completely. Identify the problem class:

Problem	Signal	Fix
Undertriggering	skill doesn't load	add keywords, trigger phrases, file types to description
Overtriggering	loads for unrelated queries	add negative triggers, be more specific
Skips body	follows description only	remove process/workflow from description
Inconsistent output	varies across sessions	add explicit templates, reduce freedom, add scripts
Too slow	large context	move detail to references/, cut body to <500 lines

Improvement mindset

1. Generalize from feedback. You're iterating on a few examples, but the skill will be used on thousands of prompts. Don't overfit — avoid fiddly patches or oppressive MUSTs for one test case. Try different metaphors or patterns instead
2. Keep the prompt lean. Read transcripts, not just outputs. If the skill makes the model waste time on unproductive steps, remove those instructions and see what happens
3. Explain the why. LLMs have good theory of mind. Instead of ALWAYS/NEVER in caps, explain the reasoning — it's more powerful and robust. If you're writing rigid rules, reframe as explanations
4. Look for repeated work. If all test runs independently write the same helper script, bundle it in scripts/. Saves every future invocation from reinventing the wheel
5. Apply the authoring canon. Read references/sop-practices.md — the 9 canonical principles (universal) map directly to skill failure modes: process leaking into description, SKILL.md bloated instead of a map, env/keys inlined, silent improvisation from missing "why", missed edge cases, agents skipping end-of-doc checklists. For process skills (ticket, quote, escalation) also apply the deep SOP methodology in the same file

Step 2: Eval Iteration Loop

The improvement cycle mirrors CREATE Step 6, but focused on the broken behavior:

1. Run the failing case with current skill → document failure
2. Apply fix using writing rules from CREATE Step 5
3. Run eval again → grade with agents/grader.md
4. Launch viewer: uv run eval-viewer/generate_review.py <workspace>
   • Headless/Cowork: use --static <output.html> instead of live server
5. Review, provide feedback, iterate

Step 3: Self-Update Loop

Drive iteration off failing BinEval questions, not taste. Run the loop:

1. Generate questions and evaluate the skill (see Mode 3 Stage 3 + references/bineval-method.md) → collect failing[]
2. Spawn agents/analyzer.md as note-taker: turn the failing questions + their explanations into generalized, deduped lessons (not one-off patches for a single test case)
3. Apply targeted edits addressing those lessons
4. Re-evaluate. Revert any edit that introduces a NEW failing question.
5. Terminate when failing[] (or its critical subset) is empty, or after 3 iterations. Keep the best result by gate_passed first, then overall S.

Step 3b: Blind Comparison (optional, for major changes)

When you have two meaningfully different versions:

1. Run both versions on the same evals
2. Spawn agents/comparator.md — answers the SAME binary questions for outputs A and B without knowing which skill produced which
3. Comparator reports per-dimension yes-rate for each version; winner = higher overall yes-rate, tiebreak = critical-dimension yes-rate
4. Spawn agents/analyzer.md — unblinds results, analyzes WHY the winner won
5. Apply insights to improve the losing version

This prevents bias. The comparator judges output quality, not skill design.

---

Mode 3: VALIDATE

Three stages, run in order.

Stage 1: Structural Validation

uv run scripts/eval_skill.py <skill-folder>

Checks: frontmatter, naming, description quality, process leak detection, body size, structure, scripts. Target: 10/10, no warnings.

Stage 2: Discovery (trigger testing)

Generate 6 test prompts:

• 3 that SHOULD trigger the skill
• 3 that should NOT (similar-sounding but wrong domain)

Run each in clean session. Target: 6/6 correct.

For automated trigger testing at scale, use:

uv run scripts/run_eval.py --eval-set <path> --skill-path <path> --runs-per-query 3

Stage 3: BinEval Scoring

Evaluate with atomic binary yes/no questions across 5 dimensions — each answered 1/0 with evidence. See references/bineval-method.md for the method, references/quality-questions.md for the question bank, and agents/bineval.md for the evaluator that emits bineval.json.

The 5 dimensions: Discovery, Clarity, Structure, Robustness, Completeness.

Questions come from two sources:

• Deterministic — emitted by scripts/eval_skill.py --json (the sole emitter), e.g. DET-STRUCT-SKILLMD-EXISTS, DET-DISCOVERY-DESC-PRESENT. Some are flagged critical.
• Generated — per-skill binary questions via the two-step meta-prompt (summarize the skill into requirements → decompose each into ≥1 yes/no question with a violation example).

Aggregate: per-dimension dimension_scores S_d = mean of that dimension's answers; overall S = mean of all answers.

Display bands: S≥0.90 production-ready · 0.70–0.89 solid · 0.50–0.69 needs-work · <0.50 rewrite.

GATE = every critical question (deterministic + critical bank questions) answered 1. The GATE is the pass criterion — not the scalar S.

---

Mode 4: REVIEW

Quick quality gate for third-party skills.

Checklist (pass/fail)

[ ] SKILL.md exists, exact case
[ ] Valid YAML frontmatter (name + description)
[ ] name: kebab-case, matches folder, ≤64 chars
[ ] description: ≤1024 chars, no angle brackets
[ ] description has triggers ("Use when...")
[ ] description has NO workflow/process steps
[ ] No README.md inside skill folder
[ ] SKILL.md < 500 lines
[ ] References max 1 level deep
[ ] Scripts tested and executable
[ ] No hardcoded paths/tokens/secrets

Then run VALIDATE Stage 2 (discovery) on the description. Report score + checklist.

The deterministic subset of this checklist is emitted as binary BinEval question records by scripts/eval_skill.py --json (e.g. DET-STRUCT-SKILLMD-EXISTS, DET-DISCOVERY-DESC-PRESENT, DET-ROBUST-NO-SECRETS) — the sole emitter of those records.

The checklist exists because these are the failure modes that actually happen in practice — especially process-in-description, which causes the agent to skip the body entirely.

---

Mode 5: OPTIMIZE

Automated description optimization. The description competes with other skills for Claude's attention — optimization finds the wording that triggers most accurately.

How it works

1. Create an eval set: 20 queries (10 should-trigger, 10 should-not)

Writing good eval queries

Queries must be realistic — concrete, detailed, with file paths, context, abbreviations, typos. Not "Format this data" but "my boss sent Q4 sales final FINAL v2.xlsx, add profit margin % column, revenue is col C costs col D".

Should-trigger (10): Different phrasings of the same intent — formal, casual, implicit. Include cases where user doesn't name the skill but clearly needs it. Add competing-skill edge cases.

Should-NOT-trigger (10): Near-misses that share keywords but need something different. Adjacent domains, ambiguous phrasing. "Write fibonacci" as negative for PDF skill = useless — too easy. Make negatives genuinely tricky.

Triggering mechanics: Claude only consults skills for tasks it can't handle directly. Simple queries ("read this PDF") won't trigger skills regardless of description — Claude handles them with basic tools. Eval queries must be substantive enough that consulting a skill would help.

2. Review queries in the browser: assets/eval_review.html
3. Run the optimization loop:

uv run scripts/run_loop.py \
  --eval-set evals/eval_set.json \
  --skill-path <skill-dir> \
  --model claude-sonnet-4-20250514 \
  --max-iterations 5 \
  --holdout 0.4 \
  --verbose

The loop:

• Splits queries into train (60%) and test (40%) to prevent overfitting
• Each iteration: evaluates current description → Claude proposes improvement → re-evaluates
• Improvement model sees only train results (blinded to test)
• Selects the best description by test score
• Opens live HTML report automatically

Supporting scripts

Script	Purpose
scripts/run_eval.py	Run trigger evaluation on a description
scripts/improve_description.py	Claude proposes improved description
scripts/generate_report.py	HTML visualization of optimization history
scripts/aggregate_benchmark.py	Statistical aggregation of benchmark runs

---

Mode 6: PACKAGE

1. Run REVIEW checklist (Mode 4)
2. Validate:

uv run scripts/quick_validate.py <skill-folder>

3. Package:

uv run scripts/package_skill.py <skill-folder> [output-dir]

Creates skill-name.skill (zip with .skill extension). Verify: unzip in temp dir, check structure intact.

---

Quick Reference

Skill categories

1. Document/Asset Creation — consistent output (docs, designs, code)
2. Workflow Automation — multi-step processes with methodology
3. MCP Enhancement — workflow guidance on top of tool access
4. Procedural / Process — business procedures with decision points and exceptions (handling a request, generating a quote, processing an invoice, onboarding, escalation). For these → read references/sop-practices.md

File purposes

Directory	Loaded?	Purpose
SKILL.md	on trigger	brain — instructions
references/	on demand	detailed docs, schemas
scripts/	executed, not loaded	deterministic operations
assets/	never loaded	templates, images

Progressive disclosure budget

Level	When loaded	Budget
Frontmatter	always (system prompt)	~100 words
SKILL.md body	on trigger	<500 lines
Bundled resources	on demand	unlimited

Description formula

[What it does] + Use when [triggers, file types, symptoms]. + Do NOT use for [negatives].

Reference Files

Path	What's inside
agents/grader.md	Evidence-based assertion grading
agents/comparator.md	Blind A/B output comparison
agents/analyzer.md	Post-hoc analysis + benchmark notes
agents/bineval.md	BinEval evaluator — emits bineval.json
references/patterns.md	5 architectural patterns + anti-patterns
references/schemas.md	JSON schemas for evals, grading, benchmark
references/bineval-method.md	BinEval method: dimensions, scoring, GATE
references/quality-questions.md	BinEval question bank (deterministic + bank)
references/sop-practices.md	Canon: 9 authoring principles (universal) + deep SOP methodology for procedural skills
references/runtime-setup.md	Pre-flight: uv/env/path checks, LLM-access options
eval-viewer/	Interactive HTML viewer for eval results
assets/eval_review.html	Trigger eval set editor
scripts/eval_skill.py	Structural validation (10-point scoring)
scripts/init_skill.py	Skill scaffolder
scripts/run_eval.py	Trigger evaluation runner
scripts/run_loop.py	Eval + improve optimization loop
scripts/improve_description.py	Claude-powered description improvement
scripts/aggregate_benchmark.py	Benchmark statistics aggregator
scripts/generate_report.py	HTML report generator
scripts/quick_validate.py	Quick validation for packager
scripts/test_smoke.py	Smoke tests for all scripts (12 tests)
scripts/package_skill.py	Skill → .skill packager
scripts/utils.py	Shared utilities (parse_skill_md)