designing-workflow-skills

name	designing-workflow-skills
description	Architects workflow SKILL.md files with numbered phases, routing/safety-gate/task-driven patterns, tool assignment, and progressive disclosure. Use when building or reviewing a multi-step skill structure rather than its domain content. Not for Cursor skill scaffolding (create-skill) or hermes-agent in-repo authoring (hermes-agent-skill-authoring).
version	1.0.1

Designing Workflow Skills

Build workflow-based skills that execute reliably by following structural patterns, not prose. This is a meta-skill: it teaches skill architecture, not domain expertise.

Overview

Workflow skills are SKILL.md files that guide an agent through multi-step, phased, or routed execution. Reliability comes from structure—numbered phases, entry/exit criteria, tool assignment, and progressive disclosure—not from prose that assumes the LLM will infer ordering or intent.

This skill covers five workflow patterns, twenty anti-patterns, tool assignment rules, and a six-phase creation process. Detailed references live one hop deep in references/ and workflows/.

Essential Principles

1. The description field is the only thing that controls when a skill activates. Claude decides whether to load a skill based solely on its frontmatter description. The body—including "When to Use" and "When NOT to Use"—is only read AFTER activation. Put trigger keywords, use cases, and exclusions in the description. A bad description means wrong or missed activations regardless of body content. "When NOT to Use" should name specific alternatives: "use Semgrep for simple pattern matching" not "not for simple tasks."

2. Phases must be numbered with entry and exit criteria. Unnumbered prose produces unreliable execution order. Every phase needs: a number (Phase 1, Phase 2, ...), entry criteria (what must be true before starting), numbered actions (what to do), and exit criteria (how to know it's done).

3. Tools must match the executor. Skills use allowed-tools: in frontmatter. Agents use tools: in frontmatter. Subagents get tools from their subagent_type. Never list tools the component doesn't use. Never use Bash for operations that have dedicated tools (Glob, Grep, Read, Write, Edit). Most skills and agents should include TodoRead and TodoWrite for progress tracking during multi-step execution.

4. Progressive disclosure is structural, not optional. SKILL.md stays under 500 lines. It contains only what the LLM needs for every invocation: principles, routing, quick references, and links. Detailed patterns go in references/. Step-by-step processes go in workflows/. One level deep—no reference chains (A → B → C). All files are one hop from SKILL.md.

5. Instructions must produce tool-calling patterns that scale. Every workflow instruction becomes tool calls at runtime. If a workflow searches N files for M patterns, combine into one regex, not N×M calls. If a workflow spawns subagents per item, use batching, not one subagent per file. Apply the 10,000-file test: mentally run the workflow against a large repo and check that tool call count stays bounded. See AP-18 and AP-19 in the anti-pattern table below.

6. Match instruction specificity to task fragility. Calibrate per step:

   • Low freedom (exact commands, no variation): Fragile operations—database migrations, crypto, destructive actions. "Run exactly this script."
   • Medium freedom (pseudocode with parameters): Preferred patterns where variation is acceptable. "Use this template and customize as needed."
   • High freedom (heuristics and judgment): Variable tasks—code review, exploration, documentation. "Analyze the structure and suggest improvements."
   • A skill can mix freedom levels. A security audit skill might use high freedom for discovery and low freedom for reporting.

When to Use

• Designing a new skill with multi-step workflows or phased execution
• Creating a skill that routes between multiple independent tasks
• Building a skill with safety gates (destructive actions requiring confirmation)
• Structuring a skill that uses subagents or task tracking
• Reviewing or refactoring an existing workflow skill for quality
• Deciding how to split content between SKILL.md, references/, and workflows/

When NOT to Use

• Simple single-purpose skills with no workflow (just guidance)—write the SKILL.md directly
• Writing the actual domain content of a skill—this teaches structure, not domain expertise
• Plugin configuration (plugin.json, hooks, commands)—use plugin development guides
• Non-skill agent development—this is specifically for skill architecture

Prerequisites

• Familiarity with SKILL.md frontmatter fields (name, description, allowed-tools)
• Access to the skill's target codebase or domain context
• Pattern, anti-pattern, tool-assignment, and progressive-disclosure guidance in this skill (companion files are not required)

Procedure

Phase 1: Select a Pattern

Entry criteria: You know the skill's purpose and have a rough scope.

1. Determine how many distinct execution paths the skill has using the decision tree below.
2. Read the pattern table in this phase before committing to a pattern.

How many distinct paths does the skill have?
|
+-- One path, always the same
|   +-- Does it perform destructive actions?
|       +-- YES -> Safety Gate Pattern
|       +-- NO  -> Linear Progression Pattern
|
+-- Multiple independent paths from shared setup
|   +-- Routing Pattern
|
+-- Multiple dependent steps in sequence
    +-- Do steps have complex dependencies?
        +-- YES -> Task-Driven Pattern
        +-- NO  -> Sequential Pipeline Pattern

Pattern	Use When	Key Feature
Routing	Multiple independent tasks from shared intake	Routing table maps intent to workflow files
Sequential Pipeline	Dependent steps, each feeding the next	Auto-detection may resume from partial progress
Linear Progression	Single path, same every time	Numbered phases with entry/exit criteria
Safety Gate	Destructive/irreversible actions	Two confirmation gates before execution
Task-Driven	Complex dependencies, partial failure tolerance	TaskCreate/TaskUpdate with dependency tracking

Exit criteria: A pattern name is chosen and its skeleton from the pattern table above has been reviewed.

Phase 2: Write the Frontmatter

Entry criteria: Pattern is selected.

1. Write name in kebab-case.
2. Write description in third person with specific trigger keywords. This is the ONLY field that controls activation. Never summarize workflow steps in the description (AP-20).
3. List allowed-tools (space-delimited). Include only tools the instructions actually reference. Use the tool assignment matrix below. Include TodoRead and TodoWrite for multi-step skills.
4. Add optional fields only if needed:
   • disable-model-invocation: true — only user can invoke (not Claude)
   • user-invocable: false — only Claude can invoke (hidden from / menu)
   • context: fork — run in isolated subagent context
   • agent: Explore — subagent type (requires context: fork)
   • model: [model-name] — switch model when skill is active
   • argument-hint: "[filename]" — hint shown during autocomplete

Exit criteria: Frontmatter is complete with correct tool list and trigger-optimized description.

Phase 3: Write the Body

Entry criteria: Frontmatter is complete.

1. Write ## Essential Principles — 3–5 non-negotiable rules with WHY explanations.
2. Write ## When to Use — 4–6 specific scenarios that scope behavior after activation.
3. Write ## When NOT to Use — 3–5 scenarios with named alternatives.
4. Write the pattern-specific section (routing table, pipeline steps, phase list, or gates).
5. Write ## Quick Reference — compact tables for frequently-needed info.
6. Write ## Reference Index — links to all supporting files in references/ and workflows/.
7. Write ## Success Criteria — checklist for output validation.
8. Keep total under 500 lines. Move details to references/, step-by-step processes to workflows/.

Exit criteria: Body is complete, under 500 lines, and all file references resolve.

Phase 4: Assign Tools

Entry criteria: Body is written and you know which operations the skill performs.

1. Map component type to tool set using the matrix below.
2. Remove any tool not actually referenced in the instructions (AP-12).
3. Verify read-only components never include Write or Bash.
4. Use Glob (not find), Grep (not grep), Read (not cat)—always prefer dedicated tools (AP-11).

Component Type	Typical Tools
Read-only analysis skill	Read, Glob, Grep, TodoRead, TodoWrite
Interactive analysis skill	Read, Glob, Grep, AskUserQuestion, TodoRead, TodoWrite
Code generation skill	Read, Glob, Grep, Write, Bash, TodoRead, TodoWrite
Pipeline skill	Read, Write, Glob, Grep, Bash, AskUserQuestion, Task, TaskCreate, TaskList, TaskUpdate, TodoRead, TodoWrite
Read-only agent	Read, Grep, Glob, TodoRead, TodoWrite
Action agent	Read, Grep, Glob, Write, Bash, TodoRead, TodoWrite

Exit criteria: Tool list is minimal, correct, and matches the executor type.

Phase 5: Check Anti-Patterns

Entry criteria: Skill is drafted.

1. Review all 20 anti-patterns in the table below.
2. Run through the quick reference table below for the most common mistakes.
3. Fix any violations found.

AP	Anti-Pattern	One-Line Fix
AP-1	Missing goals/anti-goals	Add When to Use AND When NOT to Use sections
AP-2	Monolithic SKILL.md (>500 lines)	Split into references/ and workflows/
AP-3	Reference chains (A → B → C)	All files one hop from SKILL.md
AP-4	Hardcoded paths	Use {baseDir} for all internal paths
AP-5	Broken file references	Verify every path resolves before submitting
AP-6	Unnumbered phases	Number every phase with entry/exit criteria
AP-7	Missing exit criteria	Define what "done" means for every phase
AP-8	No verification step	Add validation at the end of every workflow
AP-9	Vague routing keywords	Use distinctive keywords per workflow route
AP-11	Wrong tool for the job	Use Glob/Grep/Read, not Bash equivalents
AP-12	Overprivileged tools	Remove tools not actually used
AP-13	Vague subagent prompts	Specify what to analyze, look for, and return
AP-15	Reference dumps	Teach judgment, not raw documentation
AP-16	Missing rationalizations	Add "Rationalizations to Reject" for audit skills
AP-17	No concrete examples	Show input → output for key instructions
AP-18	Cartesian product tool calls	Combine patterns into single regex, grep once, then filter
AP-19	Unbounded subagent spawning	Batch items into groups, one subagent per batch
AP-20	Description summarizes workflow	Description = triggering conditions only, never workflow steps

Exit criteria: No anti-pattern violations remain.

Phase 6: Self-Review

Entry criteria: Anti-patterns are fixed.

1. Load workflows/review-checklist.md and run through the full structured self-review.
2. Verify every file reference resolves (no broken links).
3. Verify no hardcoded paths—all internal paths use {baseDir}.
4. Run the 10,000-file test: mentally execute the workflow against a large repo and confirm tool call count stays bounded.
5. Confirm the description would trigger correctly for the intended use cases and NOT trigger for excluded cases.

Exit criteria: All checklist items pass.

Structural Anatomy

Every workflow skill needs this skeleton, regardless of pattern:

---
name: kebab-case-name
description: "Third-person description with trigger keywords — this is how Claude decides to activate the skill"
allowed-tools: Tool1 Tool2 Tool3
---

# Title

## Essential Principles
[3-5 non-negotiable rules with WHY explanations]

## When to Use
[4-6 specific scenarios — scopes behavior after activation]

## When NOT to Use
[3-5 scenarios with named alternatives — scopes behavior after activation]

## [Pattern-Specific Section]
[Routing table / Pipeline steps / Phase list / Gates]

## Quick Reference
[Compact tables for frequently-needed info]

## Reference Index
[Links to all supporting files]

## Success Criteria
[Checklist for output validation]

Skills support string substitutions: dollar-prefixed variables for arguments and session ID, and exclamation-backtick syntax for shell preprocessing. The skill loader processes these before Claude sees the file—even inside code fences—so never use the raw syntax in documentation text. See the tool assignment matrix in Phase 4 for the full variable reference.

Rationalizations to Reject

Rationalization	Why It's Wrong
"It's obvious which phase comes next"	LLMs don't infer ordering from prose. Number the phases.
"Exit criteria are implied"	Implied criteria are skipped criteria. Write them explicitly.
"One big SKILL.md is simpler"	Simpler to write, worse to execute. The LLM loses focus past 500 lines.
"The description doesn't matter much"	The description is how the skill gets triggered. A bad description means wrong or missed activations.
"Bash can do everything"	Bash file operations are fragile. Dedicated tools handle encoding, permissions, and formatting better.
"The LLM will figure out the tools"	It will guess wrong. Specify exactly which tool for each operation.
"I'll add details later"	Incomplete skills ship incomplete. Design fully before writing.

Pitfalls

• Description summarizes the workflow instead of stating trigger conditions. The description is a trigger, not a summary. Write "Use when reviewing code for security vulnerabilities, injection risks, and auth bypass" not "This skill runs a 5-phase security audit with static analysis and reporting."

• Unnumbered phases cause out-of-order execution. LLMs do not infer sequence from prose structure. Every phase must have an explicit number, entry criteria, and exit criteria.

• Reference chains (A → B → C) lose context. Each hop forces the LLM to reload context. All reference files must be exactly one hop from SKILL.md. If a reference needs to reference another file, inline the content instead.

• Hardcoded paths break portability. Use {baseDir} for all internal paths. Never hardcode ~ or /home/... paths in skill files.

• Overprivileged tool lists cause unintended actions. A read-only analysis skill with Bash can accidentally execute destructive commands. List only the tools the instructions actually reference.

• Cartesian product tool calls don't scale. If a workflow searches N files for M patterns, writing N×M individual calls will exhaust context on large repos. Combine into a single regex or batch operation. Apply the 10,000-file test.

• Unbounded subagent spawning exhausts resources. If a workflow spawns one subagent per file, a 10,000-file repo will hang. Batch items into groups and spawn one subagent per batch.

• String substitution syntax leaks into documentation. The skill loader processes $variable and !`command` syntax before Claude sees the file, even inside code fences. Never use the raw syntax when documenting it—escape or describe it indirectly.

Verification

After designing a workflow skill, verify:

1. Frontmatter check:

   Select-String -Path "SKILL.md" -Pattern "^name:" | ForEach-Object { $_.Line }
   Select-String -Path "SKILL.md" -Pattern "^description:" | ForEach-Object { $_.Line }
   Select-String -Path "SKILL.md" -Pattern "^allowed-tools:" | ForEach-Object { $_.Line }
   

   Confirm name is kebab-case, description contains trigger keywords (not workflow summary), and allowed-tools lists only used tools.

2. Line count check (must be under 500):

   (Get-Content "SKILL.md").Count
   

3. File reference resolution:

   Select-String -Path "SKILL.md" -Pattern '\[.*?\]\((references|workflows)/.*?\.md\)' -AllMatches |
     ForEach-Object { $_.Matches } |
     ForEach-Object { $_.Groups[1].Value + "/" + $_.Value } |
     ForEach-Object { if (-not (Test-Path $_)) { Write-Output "BROKEN: $_" } }
   

   Output should be empty—no broken references.

4. Hardcoded path check:

   Select-String -Path "SKILL.md" -Pattern 'C:\\Users\\|/home/|/Users/' |
     ForEach-Object { Write-Output "HARDCODED: $($_.LineNumber): $($_.Line)" }
   

   Output should be empty (unless documenting a specific machine path by design).

5. Reference chain check: Manually open each file in references/ and workflows/ and confirm none link to another reference file. All links must point back to SKILL.md or external URLs only.

6. Success criteria checklist:

   • Has When to Use AND When NOT to Use sections
   • Uses a recognizable pattern (routing, pipeline, linear, safety gate, or task-driven)
   • Numbers all phases with entry and exit criteria
   • Lists only the tools it actually uses (least privilege)
   • Keeps SKILL.md under 500 lines with details split into companion reference and workflow files
   • Has no hardcoded paths (uses {baseDir})
   • Has no broken file references

Reference Index

Topic	Content	When to use
Workflow patterns	5 patterns with structural skeletons and examples	Phase 1: before selecting a pattern (table above)
Anti-patterns	20 anti-patterns with before/after fixes	Phase 5: before reviewing the draft (table above)
Tool assignment	Tool selection matrix, component comparison, subagent guidance	Phase 4: when assigning tools
Progressive disclosure	Content splitting rules, the 500-line rule, sizing guidelines	Phase 3 / Essential Principle 4
Creation process	6-phase creation from scope to self-review	Phases 1–6 in this skill
Self-review	Structured checklist for submission readiness	Phase 6 and Verification below

Related Skills

• progressive-disclosure-guide — Content splitting rules and the 500-line rule
• tool-assignment-guide — Tool selection matrix and subagent guidance
• anti-patterns — Full catalog of 20 anti-patterns with fixes