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project-planning

Deep project planning workflow—goals and non-goals, work breakdown, dependencies, critical path, risks and buffers, milestones, and communication rhythm. Use when kicking off initiatives, replanning after slips, or coordinating cross-team delivery.

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SKILL.md (original)

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Project Planning (Deep Workflow)

Plans are hypotheses—update them as facts arrive. Strong plans surface dependencies early and make trade-offs explicit (scope, date, quality).

When to Offer This Workflow

Trigger conditions:

  • Multi-team effort with a hard date or external dependency
  • Timeline slip and need to re-baseline honestly
  • Scope creep without prioritization conversation

Initial offer:

Use six stages: (1) frame outcome, (2) decompose work, (3) map dependencies, (4) schedule & buffers, (5) risks & mitigations, (6) operating rhythm. Confirm planning style (milestone-based, agile release train, hybrid).


Stage 1: Frame Outcome

Goal: Problem statement, success criteria, non-goals, constraints (date, budget, compliance).

Exit condition: One-page charter stakeholders can align on.


Stage 2: Decompose Work

Goal: Epics or WBS → trackable chunks—not necessarily micro-tasks unless execution needs it.

Practices

  • Prefer vertical slices (end-to-end thin features) over “all backend first” when possible

Stage 3: Map Dependencies

Goal: External teams, vendors, legal, security, infra—on critical path.

Practices

  • Include lead time for reviews and procurement

Exit condition: Dependency table: item, owner, need-by date, status.


Stage 4: Schedule & Buffers

Goal: Identify critical path; buffer risky unknowns, not every line uniformly.

Practices

  • Milestones with demo-ready acceptance criteria

Stage 5: Risks & Mitigations

Goal: Top risks with likelihood/impact, owner, mitigation, and trigger for plan B.


Stage 6: Operating Rhythm

Goal: Steady cadence: weekly tactical sync, steering at milestones, RAID log updates, decision log to avoid re-litigation.


Final Review Checklist

  • Charter: goals, non-goals, constraints
  • Work breakdown with vertical slices where feasible
  • Dependencies with owners and dates
  • Schedule reflects critical path and buffers
  • Risks tracked with mitigations
  • Communication cadence agreed

Tips for Effective Guidance

  • Plans usually fail on hidden dependencies—make them visible.
  • Fixed scope + fixed date + fixed quality: pick two explicitly.
  • Agile still benefits from milestone intent for cross-company coordination.

Handling Deviations

  • Research-heavy work: timebox spikes before committing delivery dates.
  • Small teams: minimum viable RAID + weekly priority still helps.

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