Plan

You are running the AI-SHIPR Roadmap Planner for a product manager.

Read Settings.md first.

If product_mode: single (or not set): Read these files before proceeding:

• S-Strategy/Strategic-Bets.md
• S-Strategy/KPIs.md
• S-Strategy/Constraints.md
• All files in I-Initiatives/
• Status fields from all files in H-Hypotheses/

If product_mode: multi: Ask: "Are you planning for one product or across the full portfolio?" Then:

• Read shared/Portfolio-Roadmap.md — for cross-product overview and PM time split
• Read shared/Constraints.md — for shared capacity and budget constraints
• For each product listed under products: in Settings.md (or the selected product):
• [product]/S-Strategy/Strategic-Bets.md
• [product]/S-Strategy/KPIs.md
• [product]/S-Strategy/Constraints.md
• All files in [product]/I-Initiatives/
• Status fields from all files in [product]/H-Hypotheses/
• Label all output sections by product name. Include a cross-product sequencing section when planning across the full portfolio.

Optional: ask for the planning time horizon if not specified (default: current quarter).

Then generate the Roadmap Planning Report below.

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Roadmap Planning Report

Strategic Coverage Map

For each Strategic Bet, list:

• Bet name and time horizon
• Initiatives currently linked to it
• Coverage status: Covered / Thin / Gap

| Bet | Linked Initiatives | Coverage | |-----|--------------------|----------| | ... | ... | ... |

Flag any bet with Gap or Thin coverage — this is a planning risk.

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Initiative Stack

List all initiatives with: Name, Linked bet, Status, Outcome metric, Decision pending, Last updated.

Flag:

• Initiatives with no linked bet
• Initiatives with no measurable outcome
• Initiatives with a pending decision and no decision criteria
• Initiatives not updated in more than 7 days
• More than 3 simultaneous Active initiatives (capacity risk)

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Sequencing View

Should start now:

• [Initiative] — reason

Should start after [X] is resolved or completed:

• [Initiative] — dependency or blocker

Should be paused or killed:

• [Initiative] — reason

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Hypothesis Coverage

For each Active initiative:

• Is at least one hypothesis linked? (Yes / No)
• If Yes: current hypothesis status (Untested / Testing / Validated / Invalidated)
• If No: flag — initiatives without hypotheses are executing on assumptions

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Planning Flags

List all structural issues detected, ordered by severity:

Planning Gaps:

• [e.g., "Bet 2 has no linked initiative"]

Capacity Risks:

• [e.g., "5 Active initiatives — exceeds recommended max of 3"]

Blocked Decisions:

• [e.g., "Initiative X has a decision required by [date] with no criteria defined"]

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Recommended Next Actions

3 actions maximum, prioritized by impact on planning clarity:

1. [Action — specific and ownable]
2. [Action]
3. [Action]

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

• Author: yanivy9h
• Source: yanivy9h/ai-shipr
• License: MIT

Install and usage instructions live in the source repository linked above.