Plan Maker
Purpose
Produce a single, goal-aligned macro-level roadmap as a Markdown document that can guide execution without modifying the codebase.
When to use
Use the plan-maker skill when:
- •Strong trigger: The user explicitly asks for a saved "roadmap" document/artifact - MUST use the
plan-makerskill unless the change is trivial (< 30 min) - •The user asks for a plan/milestones/implementation plan before coding
- •The user asks to "align thinking first" or "clarify direction" before planning
- •The task is large/ambiguous and benefits from staged execution and verification
- •You need a roadmap artifact saved under
dev-docs/active/for collaboration and handoff
Avoid the skill when:
- •The change is trivial (<30 min) and does not benefit from staged execution/verification
- •A roadmap already exists and only minor edits are needed (update the existing roadmap instead)
Inputs
- •Task goal (required)
- •If the goal is ambiguous or missing critical constraints, you MUST ask clarifying questions before drafting the roadmap.
- •Requirements source (optional):
- •Existing document: User provides a path to an existing requirements document; plan-maker reads and extracts key points
- •Interactive collection: Collect requirements through Q&A dialogue with the user
- •Both: Read existing document AND supplement with interactive Q&A
- •Requirements alignment mode (optional):
- •If user requests "align thinking first" or "clarify direction", generate requirements document to
dev-docs/active/<task>/requirement.mdbefore creating roadmap - •See
./templates/requirement.mdfor the requirements document template
- •If user requests "align thinking first" or "clarify direction", generate requirements document to
Outputs
- •
dev-docs/active/<task>/roadmap.md(always)- •
<task>is a short filesystem-safe slug derived from the goal and confirmed with the user.
- •
- •
dev-docs/active/<task>/requirement.md(optional, when requirements alignment mode is active)- •Generated when user requests "align thinking first" or provides existing requirements document
- •Host plan-mode artifact(s) (optional, read-only input)
- •May exist in the host runtime (Cursor/Codex/other planning surfaces); treat as seed input only and do not overwrite from plan-maker.
Plan-mode interoperability
- •Runtime signal contract:
- •Planning mode is active only when a reliable runtime signal exists (for example,
collaboration_mode=Plan) or the user explicitly confirms it. - •If the signal is missing, ask the user once.
- •If the signal remains unavailable and user confirmation is unavailable, continue as non-Plan mode and record that assumption.
- •Planning mode is active only when a reliable runtime signal exists (for example,
- •Seed artifact discovery order:
- •User-provided artifact paths
- •Runtime-provided host plan artifact paths
- •
dev-docs/active/<task>/requirement.md(when present or generated in Phase 0) - •Existing
dev-docs/active/<task>/roadmap.md(update flow only)
- •Merge and conflict policy (required):
- •Build the roadmap draft using set-union over available seed artifacts.
- •Resolve conflicts using the strict precedence:
- •Latest user-confirmed instruction
- •
requirement.md - •Host plan-mode artifact
- •Model inference
- •If conflicts remain unresolved, record them under roadmap open questions/assumptions and do not silently drop them.
- •Consistency baseline for dual artifacts:
- •If both host plan artifact and roadmap exist, keep semantic consistency for goal, boundaries, constraints, milestone/phase ordering, and acceptance criteria.
- •
dev-docs/active/<task>/roadmap.mdremains repository SSOT.
Steps
Phase 0 - Requirements alignment (optional, triggered by user request)
- •Check for requirements alignment request:
- •If user asks to "align thinking first" or "clarify direction", or provides an existing requirements document:
- •Proceed to step 0a
- •Otherwise, skip to step 1
- •If user asks to "align thinking first" or "clarify direction", or provides an existing requirements document:
0a. Requirements source handling:
- •If user provides an existing document path:
- •Read the document and extract: goal, use cases, boundaries, constraints
- •Summarize key points and confirm understanding with user
- •If user requests interactive collection:
- •Ask structured questions to collect:
- •Core goal (1 sentence)
- •Main use cases (2-5)
- •Boundaries / non-goals
- •Key constraints
- •Summarize collected requirements and confirm with user
- •Ask structured questions to collect:
0b. Generate requirements document (if alignment mode is active):
- •Propose
<task>slug (if not yet confirmed) - •Save aligned requirements to
dev-docs/active/<task>/requirement.md - •Confirm with user: "Requirements documented. Proceed to roadmap creation?"
- •If user confirms, continue to step 1
- •If user wants to refine, iterate on requirements document
Phase 1 - Roadmap creation (core workflow)
- •Detect planning-mode context.
- •Use runtime signal when available; otherwise ask user once.
- •Discover seed artifacts.
- •Follow the required discovery order from the interoperability rules.
- •Restate the goal in one sentence and confirm direction.
- •Identify what is unclear and ask clarifying questions.
- •Ask only what is necessary to align the roadmap to the goal (scope, non-goals, target environment, success criteria, constraints).
- •If the user cannot answer now, record assumptions explicitly and surface the risk.
- •Propose a
<task>slug and confirm the<task>slug with the user.- •Use kebab-case; avoid dates unless requested.
- •If already confirmed in Phase 0, skip step 5.
- •Draft the roadmap using
./templates/roadmap.md.- •Keep the roadmap macro-level: phases, milestones, deliverables, verification, risks, rollback.
- •Always include the Project structure change preview (may be empty) section from the template:
- •Use the section as a non-binding alignment aid (humans confirm expected impact early; execution may differ).
- •Prefer directory-level paths by default; use file-level paths only when you have clear evidence.
- •Do not guess project-specific paths or interfaces; if you have not inspected the repo, keep
(none)or use<TBD>. - •If unknown, keep
(none)or use<TBD>and add/keep a Discovery step to confirm.
- •Include input trace and merge/conflict decisions in the roadmap draft.
- •If plan-mode artifacts are available, use them as first-pass inputs and merge by union.
- •Apply strict conflict precedence: user-confirmed > requirement.md > host artifact > inference.
- •If planning-mode signal is unavailable and user confirmation is unavailable, proceed as non-Plan mode and record the assumption.
- •Only include specific file paths/APIs elsewhere when you have evidence; otherwise add a discovery step.
- •Include an "Optional detailed documentation layout (convention)" section that declares the expected file layout under
dev-docs/active/<task>/without creating those files.
- •Save the roadmap to
dev-docs/active/<task>/roadmap.md. - •Return a short handoff message to the user:
- •confirmed goal
- •where the roadmap was saved
- •the next 3 actions to start execution (without executing them)
Phase 2 - dev-docs linkage (conditional)
- •Evaluate dev-docs Decision Gate:
- •Check if task meets any of these criteria:
- •Expected duration > 2 hours, or likely to span multiple sessions
- •The work will be paused/handed off, or the user explicitly needs context recovery artifacts
- •The change is high-risk or cross-cutting (e.g., DB/schema migration, auth/security, CI/CD/infra, multi-service/API boundary changes)
- •If criteria are met:
- •Inform user: "The task qualifies for a full dev-docs bundle for context preservation."
- •Ask: "Would you like to create the complete documentation bundle now?"
- •If user confirms, trigger
create-dev-docs-planskill with the roadmap as input
- •If criteria not met:
- •Note in the handoff message that roadmap is sufficient for the current task
- •Check if task meets any of these criteria:
Verification
- • Goal is restated and (where needed) confirmed with the user
- • Ambiguities are resolved or recorded as explicit open questions/assumptions
- • (If alignment mode) Requirements document saved to
dev-docs/active/<task>/requirement.md - • (If alignment mode) User confirmed requirements understanding before roadmap creation
- • Planning-mode signal was checked; if missing, user was explicitly asked once before assuming non-Plan mode
- • Seed artifact discovery order was applied and recorded
- • Merge/conflict resolution applied strict precedence (user-confirmed > requirement.md > host artifact > inference)
- • Unresolved conflicts are preserved as open questions/assumptions
- • (If dual artifacts) Goal, boundaries, constraints, milestones/phases, and acceptance criteria are semantically consistent
- • Roadmap includes milestones/phases and per-step deliverables
- • Roadmap includes "Project structure change preview" section (may be empty)
- • Roadmap defines verification/acceptance criteria and a rollback strategy
- • Roadmap is saved to
dev-docs/active/<task>/roadmap.md - • dev-docs Decision Gate evaluated; user prompted for full bundle if criteria met
- • No application/source/config files were modified
Boundaries
- •MUST NOT modify application/source code, project configuration, or database state
- •MUST ask clarifying questions when the goal or constraints are ambiguous
- •MUST NOT invent project-specific facts (APIs, file paths, schemas) without evidence
- •MUST use the
plan-makerskill when the user explicitly asks for a saved "roadmap" document/artifact (strong trigger) - •MUST NOT assume planning mode unless a runtime signal exists or the user explicitly confirms planning mode
- •MUST default to non-Plan mode when no reliable signal or user confirmation is available, and record this assumption
- •MUST treat
dev-docs/active/<task>/roadmap.mdas repository SSOT - •MUST apply conflict precedence: user-confirmed > requirement.md > host plan artifact > inference
- •If the user asks to implement immediately but the task is non-trivial, produce the roadmap first, then ask for confirmation to proceed with execution in a follow-up turn.
- •If the task meets the dev-docs Decision Gate, MUST prompt user whether to continue with
create-dev-docs-plan - •If user confirms dev-docs bundle creation, MUST trigger
create-dev-docs-planskill - •SHOULD keep the roadmap macro-level; deep design details belong in separate documentation artifacts
- •SHOULD NOT include secrets (credentials, tokens, private keys) in the roadmap
- •SHOULD preserve semantic consistency across dual artifacts while documenting intentional divergences
- •PRODUCES macro-level roadmaps: milestones, phases, scope, impact, risks, rollback strategy
- •PRODUCES requirements documents (when alignment mode is active)
- •DOES NOT produce implementation-level documentation (architecture diagrams, step-by-step code guides, pitfalls logs)
- •The roadmap is a planning artifact; detailed implementation docs belong to a separate documentation bundle
Included assets
- •Templates:
- •
./templates/roadmap.md(roadmap document) - •
./templates/requirement.md(requirements alignment document)
- •
- •Reference:
./reference/detailed-docs-convention.md(optional file layout convention) - •Example:
./examples/sample-roadmap.md