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Interactive roadmap creation through structured questioning, optimized for ephemeral execution

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SKILL.md

name roadmap-builder
description Interactive roadmap creation through structured questioning, optimized for ephemeral execution
when_to_use when user wants to create a new development roadmap
version 3.0.0

Roadmap Builder

Create execution-ready roadmap through one-question-at-a-time dialogue.

Process

Ask questions one at a time. Use AskUserQuestion tool with clear options.

Questions Sequence

1. Project name?

  • Free text input
  • Example: "Calculator CLI"

2. Programming language?

  • Options: Python, Go, Rust, TypeScript, Java, Other
  • If Other: ask for specific language

3. Test command?

  • Show common options for selected language:
    • Python: pytest tests/ -v
    • Go: go test ./... -race -cover
    • Rust: cargo test
    • TypeScript: npm test or jest
    • Java: mvn test or gradle test
  • Allow custom command

4. Lint command?

  • Show common options for selected language:
    • Python: ruff check . or pylint
    • Go: golangci-lint run ./...
    • Rust: cargo clippy --all-targets
    • TypeScript: eslint .
    • Java: mvn checkstyle:check
  • Allow custom command

5. One-sentence project goal?

  • Free text input
  • Example: "Build a command-line calculator with expression parsing"

6. How many phases?

  • Options: 2, 3, 4, 5, 6, More than 6
  • Recommend: 3-6 phases for most projects

7-N. For each phase, ask:

  • Phase name? (e.g., "Foundation", "Core Feature", "Integration")
  • Phase goal? (one sentence, what this phase accomplishes)
  • Success criteria? (2-4 measurable outcomes)
    • Ask: "What are 2-4 things that must work when this phase is done?"
    • Examples: "Calculator.add() works", "Tests pass", "CLI parses input"

Build Roadmap YAML

After gathering all info, create roadmap at: docs/roadmaps/[YYYY-MM-DD]-[project-name-slug]-roadmap.yml

Format:

proj:
  name: "[Project Name]"
  lang: "[Language]"
  test: "[Test Command]"
  lint: "[Lint Command]"
  goal: "[One-sentence goal]"

phases:
  - id: 0
    name: "[Phase Name]"
    goal: "[Phase goal]"
    success:
      - "[Success criterion 1]"
      - "[Success criterion 2]"
      - "[Success criterion 3]"

  - id: 1
    name: "[Phase Name]"
    goal: "[Phase goal]"
    success:
      - "[Success criterion 1]"
      - "[Success criterion 2]"

Validate Roadmap

Check:

  • All required fields present
  • Phase IDs sequential (0, 1, 2, ...)
  • Each phase has 2-4 success criteria
  • Valid YAML syntax

Output

Display:

✅ Roadmap created: docs/roadmaps/[filename]

Project: [name]
Language: [lang]
Phases: [count]

To execute:
/autonomous-dev docs/roadmaps/[filename]

To review first:
cat docs/roadmaps/[filename]

Tips for Good Roadmaps

Phase granularity:

  • Each phase: 2-8 hours of work
  • Too small: overhead of phase management
  • Too large: hard to review, risky

Success criteria:

  • Specific and measurable
  • Testable (can verify with command)
  • Clear definition of done

Phase sequencing:

  • Foundation first (structure, utilities)
  • Core features next (main functionality)
  • Integration/polish last (CLI, API, docs)

Examples:

Good success criteria:

  • "Calculator.add() returns correct sum"
  • "Parser handles nested parentheses"
  • "CLI prints result to stdout"

Bad success criteria:

  • "Code is good" (not measurable)
  • "Everything works" (not specific)
  • "Ready for production" (ambiguous)