AILANG Sprint Planner

Create comprehensive, data-driven sprint plans by analyzing design documentation, current implementation status, and recent velocity.

Quick Start

Most common usage:

# User says: "Plan the next sprint based on v0.4.0 roadmap"
# This skill will:
# 1. Read design doc (design_docs/planned/v0.4-roadmap.md)
# 2. Analyze CHANGELOG for recent velocity
# 3. Review current implementation status
# 4. Propose realistic milestones with LOC estimates
# 5. Create day-by-day task breakdown

When to Use This Skill

Invoke this skill when:

• User says "plan sprint", "create sprint plan", "plan next phase"
• User asks to estimate timeline for a feature or design doc
• User wants to know how long implementation will take
• User needs to prioritize work for upcoming development

Documentation URLs

When planning sprints that involve adding error messages, help text, or documentation links:

Website: https://ailang.sunholo.com/

Documentation Source: The website documentation lives in this repo at

docs/

• Markdown files:

  docs/docs/

  (guides, reference, etc.)
• Static assets:

  docs/static/

• Docusaurus config:

  docs/docusaurus.config.js

Common Documentation Paths:

• Language syntax:

  /docs/reference/language-syntax

• Module system:

  /docs/guides/module_execution

• Getting started:

  /docs/guides/getting-started

• REPL guide:

  /docs/guides/getting-started#repl

• Implementation status:

  /docs/reference/implementation-status

• Benchmarking:

  /docs/guides/benchmarking

• Evaluation:

  /docs/guides/evaluation/README

Full URL Example:

https://ailang.sunholo.com/docs/reference/language-syntax

Best Practices:

• When planning features that include documentation links, verify the URLs exist before including them in sprint estimates
• Look in

  docs/docs/

  to verify the file exists locally
• Use

  ls docs/docs/reference/

  or

  ls docs/docs/guides/

  to find available pages

Role in Long-Running Agent Pattern

sprint-planner acts as the "Initializer" agent in the two-phase pattern from Anthropic's long-running agent article:

• Initializer (sprint-planner): Creates infrastructure for execution

  • Analyzes design docs and calculates velocity
  • Creates markdown sprint plan (human-readable)
  • NEW: Creates JSON progress file (machine-readable)
  • Sets up session resumption infrastructure
  • Sends handoff message to sprint-executor

• Coding Agent (sprint-executor): Works incrementally across sessions

  • Reads JSON progress file on each session start
  • Updates only

    passes

    field as milestones complete
  • Can pause/resume work across multiple sessions

This separation enables multi-session continuity - sprints can span days or weeks with Claude resuming work from where it left off.

Available Scripts

scripts/analyze_velocity.sh [days]

Analyze recent development velocity from CHANGELOG and git commits.

Usage:

# Analyze last 7 days (default)
.claude/skills/sprint-planner/scripts/analyze_velocity.sh

# Analyze last 14 days
.claude/skills/sprint-planner/scripts/analyze_velocity.sh 14

Output:

Analyzing velocity for last 7 days...

=== Recent CHANGELOG Entries ===
Total: ~1,200 LOC
Total: ~800 LOC

=== Recent Commits (last 7 days) ===
abc1234 Complete M-DX1.5: Migrate all builtins
def5678 Add Type Builder DSL

=== Files Changed (last 7 days) ===
15 files changed, 1200 insertions(+), 300 deletions(-)

=== Velocity Summary ===
Based on CHANGELOG entries and git history, estimate:
- Average LOC/day from recent milestones
- Typical milestone duration
- Current development pace

scripts/create_sprint_json.sh <sprint_id> <sprint_plan_md> [design_doc_md]

NEW: Create structured JSON progress file for multi-session sprint execution.

Usage:

# Create JSON progress file from sprint plan
.claude/skills/sprint-planner/scripts/create_sprint_json.sh \
  "M-S1" \
  "design_docs/planned/v0_4_0/m-s1-sprint-plan.md" \
  "design_docs/planned/v0_4_0/m-s1-parser-improvements.md"

What it does:

• Creates

  .ailang/state/sprints/sprint_<id>.json

  with feature list
• Implements "constrained modification" pattern (only

  passes

  field changes)
• Enables session resumption via structured state
• Provides template for milestone details (to be filled in)

Output:

• JSON progress file at

  .ailang/state/sprints/sprint_<id>.json

• Validation check
• Next steps instructions (edit JSON, send handoff message)

File Organization: Sprint JSON files are stored in

.ailang/state/sprints/

to keep the state directory organized.

Integration with sprint-executor: After creating the JSON file, sprint-executor can:

• Resume work across multiple Claude Code sessions
• Track progress programmatically
• Update velocity metrics automatically

Sprint Planning Workflow

CRITICAL: Always end by handing off to sprint-executor after user approval!

1. Read and Analyze Design Document

Input: Path to design doc (e.g.,

design_docs/planned/v0.4-roadmap.md

)

What to extract:

• Completed milestones (marked ✅)
• Remaining milestones (marked ❌, ⏳, 📋)
• Target metrics (LOC estimates, timeline, acceptance criteria)
• Dependencies between milestones

2. Review Current Implementation Status

Check these sources:

• CHANGELOG.md

  - Recent features and LOC counts

• git log --oneline --since="1 week ago"

  - Actual commits

• make test-coverage-badge

  - Current test coverage
• Design doc vs reality - gaps or partial implementations

3. Analyze Recent Velocity

Use the velocity script:

.claude/skills/sprint-planner/scripts/analyze_velocity.sh

Calculate:

• LOC per day from recent milestones
• Average milestone duration
• Actual completion rate vs estimates

4. Identify Remaining Work

List incomplete milestones with:

• Dependencies (what blocks what)
• Estimated effort (from design doc)
• Priority (based on dependencies, critical path)
• Current velocity (can we realistically do this?)

5. Propose Sprint Plan

Use the template: See

resources/sprint_plan_template.md

Include:

• Sprint Summary: Goal, duration, key deliverables
• Milestone Breakdown: For each milestone:
  • Name and description
  • Estimated LOC (implementation + tests)
  • Example files to create/update (CRITICAL - required for every new feature)
  • Dependencies
  • Acceptance criteria
  • Risk factors
• Task List: Day-by-day breakdown (if < 1 week) or weekly (if longer)
• Success Metrics:
  • Test coverage target
  • Example files created and verified working (CRITICAL - see CLAUDE.md)
  • Docs to update

6. Present for Feedback

Show user:

• Proposed milestones with estimates
• Assumptions made
• Areas where input is needed
• Realistic timeline based on actual velocity

Be ready to revise based on user priorities or constraints.

7. Finalize and Document

Once approved:

# Create sprint plan document (markdown - human-readable)
# Naming: M-<type><number>.md (M-P1 for parser, M-T1 for types, etc.)

Include in sprint plan:

• Goal and motivation
• Technical approach
• Day-by-day implementation plan
• Acceptance criteria
• Estimated LOC
• Dependencies

NEW: Create JSON progress file (machine-readable):

# Create structured progress file for multi-session execution
.claude/skills/sprint-planner/scripts/create_sprint_json.sh \
  "<sprint-id>" \
  "design_docs/planned/vX_Y/<sprint-id>-plan.md" \
  "design_docs/planned/vX_Y/<feature>-design.md"

8. MANDATORY: Populate JSON with Real Milestones

The script creates a TEMPLATE - you MUST populate it with real data!

The

create_sprint_json.sh

script generates placeholder content. Before handing off to sprint-executor, you MUST edit the JSON file to include actual milestones.

Required edits to

.ailang/state/sprints/sprint_<id>.json

:

1. Replace placeholder features array with real milestones:

   "features": [
     {
       "id": "M1_ACTUAL_NAME",
       "description": "Real description from your sprint plan",
       "estimated_loc": 150,
       "dependencies": [],
       "acceptance_criteria": [
         "Actual criterion from sprint plan",
         "Another real criterion"
       ],
       "passes": null,
       "started": null,
       "completed": null,
       "notes": null
     }
   ]
   

2. Update velocity estimates to match your sprint plan:

   "velocity": {
     "target_loc_per_day": 150,
     "estimated_total_loc": 670,
     "estimated_days": 4
   }
   

Validation checklist before handoff:

• No milestone has

  "id": "MILESTONE_ID"

  (placeholder)
• Each milestone has real acceptance criteria (not "Criterion 1")

• estimated_total_loc

  matches sum of milestone LOC

• estimated_days

  matches sprint plan duration
• At least 2 milestones defined

sprint-executor will REJECT the sprint if placeholders remain!

8.1. Link GitHub Issues (Automatic via ailang messages)

The script automatically discovers related GitHub issues using

ailang messages

integration.

The

create_sprint_json.sh

script automatically:

1. Syncs GitHub issues via

   ailang messages import-github

2. Extracts message IDs from the design doc's "Bug Report" field (pattern:

   msg_YYYYMMDD_HHMMSS_hash

   )
3. Queries local messages for issues matching design doc keywords
4. Extracts explicit

   #123

   references from the design doc
5. Adds

   github_issues: [...]

   to the sprint JSON

Why link GitHub issues?

• Development commits use

  refs #123

  to link without closing
• Final commit uses

  Fixes #123

  to AUTO-CLOSE issue on merge
• Issues are updated with links to commits/PRs
• Audit trail from bug report → design doc → sprint → commits → release

Important: "refs" vs "Fixes"

• refs #17

  - Links commit to issue (NO auto-close) - use during development

• Fixes #17

  ,

  Closes #17

  ,

  Resolves #17

  - AUTO-CLOSES issue when merged - use in final commit

Deduplication:

ailang messages import-github

checks existing issues by number before importing. Issues are never duplicated.

Manual linking (if auto-extraction misses issues):

# Add GitHub issues to sprint JSON
jq '.github_issues = [17, 42]' .ailang/state/sprints/sprint_<id>.json > tmp && mv tmp .ailang/state/sprints/sprint_<id>.json

Example JSON with linked issues:

{
  "sprint_id": "M-BUG-FIX",
  "github_issues": [17, 42],
  "features": [...]
}

Workflow with GitHub integration:

1. External project sends bug report:

   ailang messages send user "Bug: ..." --type bug --github

2. GitHub issue #17 is created and linked to message
3. Design doc references message ID:

   **Bug Report**: msg_20251210_..._abc123

4. create_sprint_json.sh

   extracts message ID, looks up issue #17, adds to JSON
5. Sprint-executor includes

   refs #17

   in milestone commits (links, no close)
6. Final sprint commit uses

   Fixes #17

   to auto-close issue on merge

9. ALWAYS Hand Off to sprint-executor

CRITICAL: After creating an approved sprint plan, ALWAYS hand off to sprint-executor immediately.

This is the standard workflow:

1. sprint-planner (this skill): Creates plan + JSON progress file
2. sprint-executor (implementation agent): Executes the plan with TDD

Send handoff message:

ailang agent send sprint-executor '{
  "type": "plan_ready",
  "correlation_id": "sprint_<sprint-id>_<date>",
  "sprint_id": "<sprint-id>",
  "plan_path": "design_docs/planned/vX_Y/<sprint-id>-plan.md",
  "progress_path": ".ailang/state/sprints/sprint_<id>.json",
  "estimated_duration": "X days (Y hours)",
  "milestones": [
    {"id": "M1", "name": "...", "estimated_hours": X},
    {"id": "M2", "name": "...", "estimated_hours": Y}
  ],
  "discovery": "Key findings from analysis",
  "total_loc_estimate": N,
  "risk_level": "low|medium|high"
}'

Why this workflow?

• sprint-executor specializes in TDD, continuous linting, progress tracking
• Enables multi-session work (sprints can span days/weeks)
• Proper separation of concerns: planning vs execution

Optional: Commit before handoff:

git add design_docs/YYYYMMDD/M-<milestone>.md
git add .ailang/state/sprints/sprint_<id>.json
git commit -m "Add M-<milestone> sprint plan with JSON progress tracking"

Analysis Framework

Design Doc Analysis Checklist

• Current status: What's ✅ vs ❌ vs ⏳
• Timeline: Days/weeks remaining, velocity metrics
• Priority matrix: Critical vs nice-to-have
• Deferred items: Features pushed to later versions
• Technical debt: Known issues or limitations

Implementation Analysis Checklist

• CHANGELOG.md: Recent features, LOC counts, test counts
• Git history: Actual work done (not just documented)
• Test files: Coverage, test counts, test patterns
• Code files: Actual implementation, not just stubs
• TODO/FIXME: Inline comments about future work
• Example files: What works vs what's broken (check

  examples/

  directory)
• Example coverage: Does every new feature have a working example? (CRITICAL)

Gap Analysis Checklist

• Features in design doc but not implemented
• Features implemented but not in design doc
• Estimated LOC vs actual LOC (for velocity)
• Planned vs actual timeline
• Test coverage gaps
• Documentation gaps

Resources

Sprint Plan Template

See

resources/sprint_plan_template.md

for complete sprint plan structure.

Best Practices

1. Be Conservative with Estimates

• Use actual velocity from recent work
• Add 20-30% buffer for unknowns
• Don't promise more than recent velocity suggests

2. Prioritize Ruthlessly

• Focus on highest-value items first
• Don't try to do everything in one sprint
• Defer nice-to-haves to future sprints

3. Make Tasks Concrete

• ❌ "Implement X" is too vague
• ✅ "Write parser for X syntax (~100 LOC) + 15 test cases" is concrete
• Each task should be achievable in 1 day or less

4. Consider Technical Debt

• Don't just add features, also fix issues
• Balance new work with quality improvements
• Factor in time for bug fixes and refactoring

5. Plan for Testing

• Every feature needs tests
• Test LOC is usually 30-50% of implementation LOC
• Include test writing in timeline estimates

6. Document Assumptions

• Make implicit assumptions explicit
• Note areas of uncertainty
• Highlight where you need user input

7. Verify Design Doc Has Systemic Analysis

Before planning a sprint for a bug fix, verify the design doc addresses systemic issues.

The

design-doc-creator

skill includes guidance for auditing related code paths before writing a design doc. If the design doc only fixes the reported symptom without checking for similar gaps, send it back for revision.

Quick check: Does the design doc mention:

• Search for similar code paths performed?
• Other types/cases checked for same gap?
• Unified fix covering all cases (not just reported one)?

If not: Ask user to revise design doc before planning sprint.

See

design-doc-creator

skill for full systemic analysis checklist.

Output Format

See

resources/sprint_plan_template.md

for full template.

Key sections:

• Summary (goal, duration, risk level)
• Current status analysis (completed, velocity, remaining)
• Proposed milestones (with tasks, criteria, risks)
• Success metrics
• Dependencies and open questions

Progressive Disclosure

This skill loads information progressively:

1. Always loaded: This SKILL.md file (YAML frontmatter + workflow)
2. Execute as needed: Scripts in

   scripts/

   (velocity analysis)
3. Load on demand:

   resources/sprint_plan_template.md

   (template)

Scripts execute without loading into context window, saving tokens.

Notes

• This skill is interactive - expect back-and-forth with user
• Sprint plans should be realistic, not aspirational
• Use actual data (velocity, LOC counts) over guesses
• Update design docs as reality diverges from plan
• Don't commit plan until approved by user