Strategic Roadmap Management

Manage project roadmaps through five modes: sync ROADMAP.md with GitHub reality, bootstrap planning files from scratch, brainstorm new features collaboratively, get a quick status summary, or show help.

Prerequisite check

gh --version 2>/dev/null && gh auth status 2>/dev/null

If

gh

gh auth login

Constitutional principle

CONTEXT.md is the project constitution. All modes must read and respect the boundaries defined in CONTEXT.md. If CONTEXT.md exists, read it first and constrain all analysis and recommendations.

When any recommendation would violate CONTEXT.md boundaries:

1. Explicitly flag the violation
2. Explain which boundary would be crossed
3. Suggest an alternative that respects the boundaries

Mode dispatch

Determine the mode from the user's input. If no mode is specified, default to sync.

sync

generate

brainstorm

status

help

Mode: sync

Synchronize ROADMAP.md with GitHub and provide prioritized recommendations. This is the primary mode.

1. Fetch open issues, recently closed issues, and milestones via

   gh

   CLI
2. Read ROADMAP.md and CONTEXT.md
3. Check for legacy section layout — if found, ask the user whether to migrate to canonical structure (Vision → Immediate Focus → Near-Term → Future → Completed → Boundaries)
4. Detect discrepancies between ROADMAP.md and GitHub (issues marked done but still open, open but closed, missing entirely)
5. Update ROADMAP.md — fix discrepancies, move closed issues to "Completed Milestones" under quarterly sub-headings
6. Estimate LOE for open issues without

   effort/*

   labels using the heuristics in

   references/label-config.md

7. Sync GitHub labels — create missing labels, add/remove

   roadmap/*

   labels to match ROADMAP.md sections
8. Append LOE indicators (

   [S]

   ,

   [M]

   ,

   [L]

   ) to issue lines in ROADMAP.md
9. Generate 3-5 prioritized recommendations based on dependencies, impact vs effort, theme coherence, and LOE balance
10. Present summary of all changes and recommendations

For detailed workflow steps, see

references/sync.md

references/label-config.md

Mode: generate

Bootstrap CONTEXT.md and ROADMAP.md for a new or undocumented project.

1. If either file exists, ask the user: regenerate, merge, or abort
2. Investigate the codebase — structure, dependencies, entry points, capabilities
3. Infer project boundaries ("hard no's") — what the project does NOT do
4. Research externally for similar tools and industry context
5. Draft CONTEXT.md with: core identity, technical boundaries, data source of truth, interaction model, verification criteria
6. Fetch all GitHub issues and milestones
7. Categorize issues into Immediate Focus, Near-Term, Future, and Completed (grouped by quarter)
8. Estimate LOE per open issue and apply

   effort/*

   labels
9. Draft ROADMAP.md with canonical structure and LOE indicators
10. Write CONTEXT.md first, then ROADMAP.md. Run markdownlint on both.

For detailed workflow steps and templates, see

references/generate.md

references/label-config.md

Mode: brainstorm

Explore new possibilities through collaborative ideation. This mode is read-only by default — do not create issues or modify ROADMAP.md until the user explicitly approves.

1. Read CONTEXT.md and ROADMAP.md for current state and boundaries
2. Investigate the codebase for extension points, underutilized capabilities, and seams for new features
3. Research externally for similar tools, user requests, and trends
4. Use ideation techniques with the user: "What if...", "Who else...", "Why not...", "What's missing...", "What annoys..."
5. Evaluate each idea: boundary check against CONTEXT.md, effort, impact, dependencies
6. Present ideas in structured format (description, rationale, boundary check, effort, impact, next step)
7. Ask the user which ideas to formalize — only then create issues or update ROADMAP.md

For detailed workflow steps and idea template, see

references/brainstorm.md

Mode: status

Quick read-only summary of current roadmap state. No modifications.

1. Fetch issue counts and milestone progress via

   gh

   CLI
2. Read ROADMAP.md
3. Present summary tables: overall metrics, by category (enhancement/bug/docs), by LOE (small/medium/large)
4. Flag obvious discrepancies without deep analysis

For detailed workflow steps and table templates, see

references/status.md

Mode: help

Display available modes and usage:

roadmap — Strategic Roadmap Management

MODES:
  (default)    Sync ROADMAP.md + labels with GitHub, recommend priorities
  sync         Same as default
  generate     Bootstrap CONTEXT.md + ROADMAP.md from scratch
  brainstorm   Creative ideation session (collaborative, read-only)
  status       Quick read-only summary of current state
  help         Show this help message

LABELS (synced automatically):
  roadmap/current  → "Immediate Focus" section
  roadmap/next     → "Near-Term Vision" section
  roadmap/future   → "Future Vision" section
  effort/small     → 1-2 hours
  effort/medium    → half day to 1 day
  effort/large     → multi-day

KEY PRINCIPLES:
  CONTEXT.md is the project constitution (all modes respect it)
  Brainstorm mode is read-only until user approves ideas
  Generate mode asks before overwriting existing files
  Labels are synced to match ROADMAP.md sections
  LOE is auto-estimated for issues missing effort/* labels

Output guidelines

• Use tables for structured comparisons
• Use emoji sparingly and only for status indicators
• Always include issue numbers when referencing GitHub issues
• Run markdownlint after any file modifications