plan-first-development

Planning methodology and session management for software projects. Covers markdown plan creation, iterative refinement, multi-model blending, phase-based implementation docs, and cross-session progress tracking. Use when starting new projects, adding major features, breaking large work into phases, resuming after context clears, or managing multi-phase implementations.

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Install skill "plan-first-development" with this command: npx skills add oakoss/agent-skills/oakoss-agent-skills-plan-first-development

Planning

Overview

Plan-first development methodology where 80%+ of time goes to planning before implementation begins. Planning tokens are cheaper than implementation tokens, and models reason better about a detailed plan that fits their context window than about a sprawling codebase.

When to use: Starting new projects, adding major features, breaking complex work into phases, resuming work after context clears, managing multi-session implementations, coordinating multiple agents on the same codebase.

When NOT to use: Quick bug fixes, one-file changes, exploratory prototyping where requirements are unknown, trivial refactors where the change is obvious.

Quick Reference

Planning PhaseDescription
1. Initial planWrite goals, intent, workflows, tech stack
2. Iterative refinement4-5 rounds of review until suggestions plateau
3. Multi-model blendGet competing plans, merge best-of-all-worlds
4. Convert to tasksSelf-contained tasks with dependency structure
5. Polish tasks6+ rounds of cross-model review
Phase TypeScopeMax FilesDuration
InfrastructureScaffolding, build config, deployment3-51-3 hours
DatabaseMigrations, schema, seed data2-42-4 hours
APIRoutes, middleware, validation3-63-6 hours
UIComponents, forms, state, styling4-84-8 hours
IntegrationThird-party services, webhooks2-43-5 hours
TestingE2E tests, integration testsvaries3-6 hours
PatternPurposeKey Points
When to plan vs buildDecision tree by complexity signalsMatch planning depth to task complexity
Risk assessmentProbability x impact matrixFocus on high-risk items first
Session LifecycleAction
StartRead SESSION.md, check "Next Action", continue
WorkImplement, verify, debug (repeat)
CheckpointGit commit with structured format, update SESSION.md hash
WrapUpdate SESSION.md, git checkpoint, set concrete "Next Action"
ResumeRead SESSION.md + planning docs, continue from "Next Action"
DocumentWhen to Generate
Implementation phasesAlways -- core plan doc for every project
Session trackingAlways -- navigation hub for progress
Database schema3+ tables
API endpoints5+ endpoints
Architecture overviewMultiple services or complex system boundaries
Critical workflowsComplex setup steps, order-sensitive workflows
Good PlanGreat Plan
Describes what to buildExplains WHY you are building it
Lists featuresDetails user workflows and interactions
Mentions tech stackJustifies tech choices with tradeoffs
Has tasksHas tasks with dependencies and rationale
~500 lines~3,500+ lines after refinement

Common Mistakes

MistakeCorrect Pattern
Starting implementation before planning is completeSpend 80%+ of time on planning; finish all refinement rounds before writing code
Writing vague next actions like "continue API work"Be specific: "Implement PATCH /api/tasks/:id in src/routes/tasks.ts:47"
Session tracking doc over 200 linesCollapse completed phases to summaries; reference planning docs for details
Creating phases with 10+ filesAuto-split into sub-phases of 5-8 files that fit in one 2-4 hour session
Single-round plan reviewIterate 4-5 rounds until suggestions plateau; use multi-model blending for fresh perspectives
Copying code into session docsReference file paths and line numbers instead of pasting code
Duplicating planning doc content in session docLink to sections with anchors; session doc is a navigation hub
No verification criteria on phasesEvery phase needs specific, testable exit criteria (status codes, user flows, constraints)
Skeleton-first coding before a plan existsOne thorough plan beats incremental skeleton-first coding
Planning without prototyping unknown techBuild a spike first for unfamiliar frameworks, then create the plan
Over-planning simple tasksMatch planning depth to complexity; skip for trivial work
Not validating assumptions earlyRun a spike for the riskiest assumption first

Delegation

  • Explore existing codebase for architecture decisions: Use Explore agent to survey file structure, patterns, and dependencies before planning
  • Execute phase implementation with verification: Use Task agent to implement individual phases, run verification criteria, and create checkpoint commits
  • Design architecture and decompose into phases: Use Plan agent to create implementation phases with dependency ordering and gate criteria

References

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