danieldekay Project Planning Skill
Strategic planning system that produces living planning documents. Covers everything ABOVE the spec level: vision, roadmap, epics, backlog, status dashboards, and milestone reviews.
When To Use This Skill
- Creating a new project's planning structure from scratch
- Writing or updating a vision, roadmap, epic, backlog, or status dashboard
- Running a milestone review or checkpoint
- Triaging work into L1 (spec) / L2 (task-batch) / L3 (quick-fix)
- Extracting deferred items from specs into a centralized backlog
When NOT To Use This Skill
- Writing spec.md, plan.md, tasks.md → use speckit agents
- Implementing code → use spec-implementer or direct coding
- Reviewing code → use Code Review Agent
The Planning Hierarchy
VISION → EPICS → WORK ITEMS → EXECUTION
↓ ↓ ↓
L1 L2 L3
Spec Batch Fix
Every piece of work enters the hierarchy and gets triaged by size before execution.
Artifact Catalog
| Artifact | Template | When To Create | Update Frequency |
|---|---|---|---|
| Planning Session | templates/planning-session.md |
Every planner session | Once (immutable snapshot) |
| Vision | templates/vision.md |
Once per project | Rarely (strategy shifts) |
| Roadmap | templates/roadmap.md |
Once per project | When priorities change |
| Epic | templates/epic.md |
Per capability group (5–15 specs) | When epic scope changes |
| Project Status | templates/project-status.md |
Once per project | After any spec work |
| Backlog | templates/backlog.md |
Once per project | When completing or discovering items |
| Milestone Review | templates/milestone-review.md |
At each milestone boundary | Once (snapshot) |
Using Templates
- Read the template from
templates/<name>.md - Replace all
{{PLACEHOLDER}}values with project-specific content - Write to the target location (see File Locations below)
- Remove any template sections that don't apply
Planning Session Artifacts (Mandatory)
Every planner session MUST produce a dated session artifact at:
plan/sessions/YYYY-MM-DD-<topic-slug>.md
Examples:
plan/sessions/2026-03-02-situation-assessment.mdplan/sessions/2026-03-02-epic-05-breakdown.mdplan/sessions/2026-03-02-backlog-extraction.md
This creates a searchable history of planning decisions even when the main artifacts (ROADMAP, BACKLOG) are updated in-place.
Work Item Triage (L1 / L2 / L3)
See references/triage-rules.md for the complete decision tree.
Quick version:
- L1 Spec: New domain entities, cross-layer changes, 3+ user stories →
speckit.specify - L2 Task-Batch: Clear scope, no new domain concepts, 1–3 sessions → entry in backlog
- L3 Quick-Fix: Single file, <30 min, near-zero risk → just do it
When uncertain, default to L2. You can promote to L1 if complexity emerges. L1 → L2 is rare and indicates overscoping.
Backlog Management
Extracting Deferred Items
To build or refresh a backlog:
- Scan all
specs/*/future-improvements.mdfiles - Scan
plan/MVP-CHECKLIST.mdfor open blockers - Check each spec for incomplete phases or user stories
- Consolidate into
plan/BACKLOG.mdusing the backlog template - Assign IDs:
BLK-NNN(blocker),RDY-NNN(ready),SCP-NNN(needs scoping),DEF-NNN(deferred) - Assign effort level: L1, L2, or L3
Prioritization Framework
- Blockers — anything preventing other work
- Current branch — finish before starting new
- Critical path — items on the path to launch
- Multipliers — features that unlock many others
- Quick wins — high value, low effort
- Nice-to-haves — someday/maybe
Creating New Epics
Epics group 5–15 related specs into a coherent capability. Use templates/epic.md.
Rules:
- Every spec MUST belong to exactly one epic
- Epic names describe a capability, not a feature (e.g., "Entity Expansion" not "Add People")
- Include dependency links to other epics
- Track completion as aggregate of contained spec statuses
Milestone Reviews
At milestone boundaries, create a review using templates/milestone-review.md:
- What was planned vs. delivered
- What slipped and why
- Backlog items discovered during the milestone
- Scope changes for the next milestone
- Updated risk assessment
File Locations
Planning artifacts live in plan/:
plan/
├── WORKFLOW.md # How the planning system works (reference)
├── PROJECT-STATUS.md # Spec-level dashboard
├── ROADMAP.md # Milestones and execution lanes
├── BACKLOG.md # Deferred work items
├── sessions/ # Dated per-session artifacts (one per planner run)
│ └── YYYY-MM-DD-*.md
├── northstar/
│ ├── VISION.md # Strategic product truth
│ ├── TAXONOMY.md # Domain model definitions
│ ├── epics/ # Epic definitions
│ │ ├── README.md # Epic index
│ │ └── EPIC-NN-*.md # Individual epics
│ ├── personas/ # User archetypes
│ └── references/ # Brand, migration docs