Plan

Planning Checkpoint (/plan)

A structured planning skill for product and project managers. Evaluates the initiative before committing to a roadmap — scope, stakeholders, constraints, dependencies, milestones, and risks. Output is a phased plan with clear owners and done-when criteria.

Core principle: A plan that wasn't evaluated isn't a plan — it's a wishlist. Never produce a roadmap until the human has answered the 6 planning questions.

Interaction model: Use AskUserQuestion for all decision points. The AI proposes informed options (based on any available project context), the human confirms or adjusts. Same Bloom ladder as /think — tuned for PM work.

How It Differs from /think and /prebuild

Use /plan when the decision to do the thing is already made and you need to sequence and scope the work. Use /think when you're still deciding whether or why.

Framework Reference

┌─────────────────────────────────────────┐
│  Level 5: Evaluate     HUMAN → AI      │  Scope, owners, constraints
│  Level 4: Analyze      HUMAN ↔ AI      │  Dependencies, sequencing
├─────────────────────────────────────────┤
│  Level 3: Apply        AI → HUMAN      │  Produce the plan doc
│  Level 2: Understand   AI → HUMAN      │  Walk through the plan
│  Level 1: Remember     AI alone        │  Save to project tracking
└─────────────────────────────────────────┘

Commands

/plan [initiative] — Start planning

Begin a new planning session for the described initiative.

/plan continue — Resume

Resume from where a prior session left off.

/plan summary — Show state

Display completed levels, confirmed decisions, and what's next.

/plan save — Persist

Save the finalized plan to the vault or linked tracking system.

Step 1: Detect the Initiative Shape (Silent)

Classify the initiative before asking questions:

• Initiative type: Product launch, feature delivery, migration, refactor, research spike, operational improvement, compliance/regulatory, content/campaign
• Time horizon: Sprint (≤2 weeks), Quarter (1–3 months), Multi-quarter (3+ months)
• Team shape: Solo, small team, multi-team

Output one line:

Detected: [initiative type] — [brief description] ([horizon], [team shape])

Step 2: Level 5 — Evaluate (6 Planning Questions)

Split into two rounds of 3 questions each (AskUserQuestion max 4 per call).

Round 1: Outcome, Stakeholders, Constraints

AskUserQuestion (3 questions):

Question 1 — OUTCOME (header: "Outcome")
  "What specific outcome are we committing to?"
  Options — propose measurable framings:
    - "Business metric target" (e.g., revenue, conversion, retention)
    - "User outcome" (e.g., users can do X, users stop hitting Y)
    - "Learning outcome" (validated insight — even if we kill it)
    - "Delivery outcome" (thing exists, shipped, adopted internally)
  (User picks the closest; "Other" for custom)

Question 2 — STAKEHOLDERS (header: "Stakeholders")
  "Who owns, who's affected, who signs off?"
  Options — propose based on initiative type:
    - "Single owner, minimal cross-team impact"
    - "One team delivers, one team is downstream consumer"
    - "Multiple teams, needs exec alignment"
    - "External stakeholders involved (customers, vendors, regulators)"

Question 3 — CONSTRAINTS (header: "Fixed")
  "Of time / scope / quality / budget, which is fixed?"
  multiSelect: true (often 1–2 are fixed, the rest flex)
  Options:
    - "Time — hard deadline"
    - "Scope — must include X, Y, Z"
    - "Quality — cannot compromise (compliance, safety, brand)"
    - "Budget — fixed spend / headcount"

Round 2: Dependencies, Milestones, Risks

AskUserQuestion (3 questions):

Question 4 — DEPENDENCIES (header: "Depends on")
  "What must be true / done / unblocked before we can start or ship?"
  multiSelect: true
  Options — propose categories:
    - "Upstream deliverable from another team"
    - "External vendor / API / contract"
    - "Hiring or capacity"
    - "Decision or approval still pending"
    - "No hard dependencies — we can start now"

Question 5 — MILESTONES (header: "Phasing")
  "How should the work phase?"
  Options — propose shapes based on horizon:
    - "Single sprint — one push, one demo"
    - "Phased — discovery → build → launch"
    - "Iterative — weekly slices shipped continuously"
    - "Gated — each phase requires sign-off to proceed"

Question 6 — RISK (header: "Top risks")
  "Which risks most threaten the outcome?"
  multiSelect: true
  Options — propose by initiative type (see risk table below):
    - "[Initiative-specific risk A]"
    - "[Initiative-specific risk B]"
    - "[Initiative-specific risk C]"
    - "[Initiative-specific risk D]"

Risk options by initiative type

Step 3: Compile Level 5 Summary

After both rounds, display the compiled evaluation:

## Level 5 Summary

- **Outcome:** [compiled]
- **Stakeholders:** [compiled + implied RACI hints]
- **Fixed constraints:** [compiled]
- **Dependencies:** [compiled list]
- **Phasing approach:** [compiled]
- **Top risks:** [compiled list]

Moving to Level 4: Analyze...

Step 4: Level 4 — Analyze (Sequencing & Capacity)

Translate Level 5 answers into a draft timeline. Analyze:

1. Dependency graph — which items unblock which. Propose the critical path.
2. Capacity check — given the team shape, is the phasing realistic?
3. Risk-adjusted buffer — where should slack live based on top risks?
4. Decision gaps — any milestone that has an unmade decision behind it?

IMPORTANT: If analysis surfaces a new decision (e.g., "Phase 2 depends on Option A or B from another team — which?"), RETURN TO LEVEL 5 and ask via AskUserQuestion. Don't assume.

Step 5: Level 3 — Produce the Plan

Produce a structured plan document. Match the level of detail to the horizon:

Sprint plan (≤2 weeks)

• Goal (1 line), scope (bulleted), out of scope (bulleted)
• Daily/milestone breakdown
• Done-when checklist
• Single owner

Quarterly plan (1–3 months)

• Outcome statement
• Phases with entry/exit criteria
• RACI table
• Dependency list (with owner and needed-by date)
• Risk register (risk, likelihood, impact, mitigation, owner)
• Success metrics (leading + lagging indicators)

Multi-quarter plan (3+ months)

• Vision + outcome statement
• Quarterly themes with milestones
• Cross-team dependencies and coordination plan
• Review cadence (monthly / quarterly gates)
• Risk register with escalation paths
• Success metrics + review dates

Template skeleton

# Plan: [Initiative Name]

## Outcome
[From Q1 — measurable]

## Scope
**In:** [bulleted]
**Out:** [bulleted]

## Fixed constraints
[From Q3]

## Phases

### Phase 1 — [Name] ([dates])
- Entry: [criteria]
- Work: [bullets]
- Exit / Done-when: [criteria]
- Owner: [role/name]

### Phase 2 — [Name] ([dates])
...

## RACI
| Activity | R | A | C | I |
|----------|---|---|---|---|
| ...      |   |   |   |   |

## Dependencies
| Depends on | Owner | Needed by | Status |
|------------|-------|-----------|--------|
| ...        |       |           |        |

## Risks
| Risk | Likelihood | Impact | Mitigation | Owner |
|------|-----------|--------|------------|-------|
| ...  |           |        |            |       |

## Success metrics
- Leading: [indicators tracked weekly]
- Lagging: [outcome metrics tracked at end]

## Review cadence
[When/who reviews progress]

Step 6: Level 2 — Walk Through the Plan

After producing the plan, explain:

• Why phasing is shaped this way (tie back to constraints from Q3)
• Where the critical path lives (from Level 4 analysis)
• Which risks have active mitigations vs. which are just watched
• What the first concrete action is ("By end of week, [owner] does [thing]")

Tailor depth to the human:

• Senior PM: Highlights of non-obvious sequencing choices
• New to PM: Section-by-section walkthrough

Step 7: Level 1 — Save the Plan

Use AskUserQuestion to confirm destination:

AskUserQuestion (1 question):

Question: "Where should we save this plan?"
Header: "Save to"
Options:
  - "Vault: ~/SecondBrain/01-projects/[initiative]/plan.md" (Recommended)
  - "Linear / Jira / Notion — hand off for tracking"
  - "Don't save — this was exploratory"

Always include:

• Frontmatter (type: plan, created: YYYY-MM-DD, status, owner, tags)
• Review date in frontmatter (e.g., review: 2026-05-01)
• Cross-links to related decisions or research in the vault

When NOT to Use

• Decision still open — Use /think first.
• Code-only task with no multi-phase shape — Use /prebuild.
• One-person, one-day task — Plans add overhead with no benefit.
• Continuous / steady-state work — Plans are for bounded initiatives.

Rules

1. NEVER produce a roadmap before Level 5 is complete. Even if the human says "just give me the plan" — at minimum ask Q1 (Outcome), Q3 (Fixed constraint), and Q6 (Risks) before drafting.
2. ALWAYS use AskUserQuestion for the 6 questions — not a text dump.
3. ALWAYS loop back to Level 5 when Level 4 surfaces a new decision. Don't guess sequencing.
4. Every milestone must have a done-when criterion. "Phase 1 complete" is not a criterion — "API deployed and 3 consumers integrated" is.
5. Every risk must have a named owner and a mitigation. Risks without owners are theater.
6. Match detail to horizon. Don't produce a quarterly template for a one-sprint task.
7. Flag the critical path explicitly. The human needs to know which item, if slipped, slips everything.