Core principle: A decision without a plan is a wish. Decompose work into tasks with dependencies, owners, timelines, and risk buffers. The plan's job is not to predict the future perfectly — it's to make the critical path visible and the risks explicit.
When to Use This Skill
- A decision has been made (decision-synthesis, architecture-evaluation, or direct commitment) and needs to be implemented
- Work involves multiple people, teams, or phases requiring coordination
- Someone asks "how long will this take?" and the honest answer requires decomposition
- A project is underway but has no visible critical path or dependency map
- An architecture decision (Contract E) needs to be turned into a build plan
Core Methodology
Step 1: Frame the Execution Context
- Decision being executed: State the committed decision. From decision-synthesis: reference the recommendation. From architecture-evaluation (Contract E): capture the ADR decision, constraints, lock-in risks, migration requirements, sequencing hints.
- Constraints: Non-negotiable boundaries — budget, team size, compliance, hard deadlines, technology lock-ins.
- Stakeholder alignment: Who has bought in, who hasn't. Residual objections (Contract B) become execution risks.
- Definition of done: An observable outcome. Not activity ("we built it") but result ("users can do X, metric Y improved").
Step 2: Build the Work Breakdown Structure
Decompose recursively: deliverables → work packages → tasks.
- Deliverables: 3-7 major outputs that, together, constitute "done"
- Work packages: Groupings of related tasks producing a deliverable (assignable to one owner)
- Tasks: Smallest unit producing a verifiable output (typically 1-5 days)
Rules:
- Every task has a verifiable output — inspectable, demoable, or testable
- No task larger than one person-week. If it is, decompose further.
- Include forgotten tasks: documentation, testing, migration, rollback planning, stakeholder communication
- Include integration tasks explicitly — "build A" and "build B" need an "integrate A with B" task
Step 3: Map Dependencies
For every task:
- What must finish before this can start? (predecessor)
- What can't start until this finishes? (successor)
- What can run in parallel? (no dependency)
Represent as a DAG. Look for:
- Sequential chains that force serialization — can any be parallelized with a different design?
- Convergence points where streams merge — high-risk coordination moments
- External dependencies — approvals, vendor deliveries, other teams' work — flag as risks
Step 4: Identify the Critical Path
The longest chain of dependent tasks from start to finish — it determines the minimum possible timeline.
- Highlight the critical path explicitly — every task on it is a schedule risk
- Tasks not on it have float (slack time). Quantify it.
- If the critical path is too long: parallelize, reduce scope, add resources to critical-path tasks, or accept the timeline
Step 5: Estimate Durations
Use reference-class estimation: estimate based on how long similar work has actually taken before, not how long you hope.
For each task, three estimates:
- Optimistic (O): everything goes right (10th percentile)
- Most likely (M): realistic with normal friction (50th percentile)
- Pessimistic (P): significant obstacles (90th percentile)
Expected duration (PERT): (O + 4M + P) / 6. Use pessimistic for critical-path tasks and external dependencies.
Common estimation failures:
- Planning fallacy: people underestimate by 50-100% on average. Calibrate against past actuals.
- Anchoring on optimism: most-likely is not optimistic
- Ignoring integration time: individual tasks estimated well, but the time to make them work together is missed
Step 6: Assign Ownership
- Owner: One person accountable for delivery (not a committee)
- Contributors: Who else is needed
- Decision authority: Can the owner make scope/approach decisions, or escalate?
RACI where coordination is complex:
- Responsible: Does the work
- Accountable: Owns the outcome (one person only)
- Consulted: Provides input before
- Informed: Notified after
Step 7: Design Milestones and Risk Buffers
Place milestones at points where progress is objectively observable — not "50% complete" but "API endpoints deployed and passing integration tests."
Risk buffers:
- Task-level: Add to high-uncertainty tasks (use the gap between most-likely and pessimistic)
- Project buffer: 15-25% of critical path duration at the end. Absorbs accumulated variance individual estimates miss.
- Feeding buffers: Where a non-critical-path stream feeds into the critical path, add a buffer at the merge point
Step 8: Surface Execution Risks and Resource Asks
Top risks paired with mitigations:
- Dependency risks: External teams, vendor delays, approval bottlenecks
- Capability risks: Skills the team doesn't have, unfamiliar technology
- Scope risks: Requirements likely to change or expand
- Integration risks: Components that must work together but built separately
For risks requiring resources, time, or scope changes beyond what's been approved, produce a resource ask in Contract C format for argument-craft:
- What's needed: Specific resource, time extension, scope change
- Why: The execution risk or critical-path constraint driving the ask
- Consequence of not getting it: What fails, degrades, or gets delayed
Output Format
🎯 Execution Objective
- Decision being executed: [decision — reference source analysis if applicable]
- Definition of done: [observable outcome that proves completion]
- Hard constraints: [budget, team, deadline, compliance, technology lock-ins]
- Stakeholder alignment status: [who's bought in, residual objections]
📋 Work Breakdown Structure
| # | Deliverable | Work Package | Task | Output | Owner | Est. Duration |
|---|---|---|---|---|---|---|
| 1.1.1 | [Deliverable 1] | [Package 1.1] | [Task] | [Verifiable output] | [Person] | [O/M/P → Expected] |
⚖️ Dependency Map
[Task 1.1.1] → [Task 1.1.2] → [Task 2.1.1] ← CRITICAL PATH
[Task 1.2.1] → [Task 1.2.2] ─────────────→ [Task 2.1.1]
(float: X days)
[Task 3.1.1] (parallel, no dependencies)
📊 Timeline and Milestones
| Milestone | Date | Proof of Completion | On Critical Path? |
|---|---|---|---|
| [Milestone] | [date] | [observable output] | Yes / No |
| Project buffer | [date range] | — | — |
👥 Ownership Matrix
| Work Package | Responsible | Accountable | Consulted | Informed |
|---|---|---|---|---|
| [Package] | [who] | [who] | [who] | [who] |
⚠️ Top Execution Risks
| Risk | Likelihood | Impact | Mitigation | Owner |
|---|---|---|---|---|
| [risk] | H / M / L | [what breaks] | [action] | [who] |
🔄 Resource Asks (Contract C → argument-craft)
| What's Needed | Why | Consequence of Not Getting It |
|---|---|---|
| [resource/time/scope change] | [risk or constraint] | [what fails or degrades] |
Thinking Triggers
- "What's on the critical path that I'm not seeing?"
- "Where are the integration points, and who owns the handoff?"
- "Am I estimating based on how long this took last time, or how long I wish it would take?"
- "What external dependency could blow up this timeline?"
- "If I had to cut scope to hit the deadline, which deliverables would I protect?"
Common Traps
Activity-based milestones: "Design phase complete" is not a milestone. "API schema reviewed and approved by consuming teams" is. Milestones must be observable from the outside.
Estimating without decomposing: "The project will take 3 months" is a guess. Break it down, estimate the pieces, and let the critical path tell you the timeline.
Ignoring the planning fallacy: Every team thinks they're the exception. Use reference-class data, not gut feel.
No project buffer: Individual estimates absorb individual variance. Project buffers absorb correlated risk — things that affect multiple tasks simultaneously (team member leaves, requirements change, integration is harder than expected).
Single-point estimates: "Takes 5 days" hides all uncertainty. Three-point estimates force you to confront what could go wrong.
Phantom parallelism: The plan shows tasks running in parallel, but the same three people are assigned to all of them. Resource-constrained scheduling is different from dependency-constrained scheduling.