Roadmap Planning

When to Use

Activate when a founder or PM has a set of product ideas, feature requests, or strategic bets and needs to organize them into a coherent roadmap. This includes situations like "help me plan our Q2 roadmap," "prioritize this feature backlog," "what should we build next," or "create a roadmap for the next 6 months." Also activate when an existing roadmap needs restructuring from output-focused (feature lists) to outcome-focused (customer and business impact).

Context Required

• From startup-context: company stage, team size and composition, current product state, business model, key metrics, strategic goals, company OKRs.
• From the user: current roadmap or list of candidate initiatives, known customer needs, resource constraints, hard deadlines, strategy documents or company objectives for alignment, and any committed work already in progress.

Workflow

1. Gather the current state -- Collect the existing roadmap or feature list. If the user provides strategy documents or company objectives, review them to understand how the roadmap should align with broader goals.
2. Transform outputs to outcomes -- For each initiative, ask: What customer problem are we solving? What business metric will improve? Is there a better way to achieve the same outcome? Rewrite each item as an outcome statement.
3. Apply outcome statement format -- Use: "Enable [customer segment] to [desired customer outcome] so that [business impact]." Every roadmap item must pass this test.
4. Score and prioritize -- Apply RICE scoring (Reach, Impact, Confidence, Effort) to rank initiatives. Adjust for strategic alignment with company objectives and OKRs.
5. Identify dependencies and sequencing -- Map which initiatives depend on others. Note technical, data, design, and business dependencies.
6. Sequence into time horizons -- Place initiatives into Now (0-6 weeks), Next (6-12 weeks), and Later (12+ weeks). Use flexible release windows (quarters, not specific dates) for Later items.
7. Validate capacity -- Cross-check the plan against team capacity. A roadmap that requires 3x your engineering bandwidth is a wishlist, not a plan.
8. Add strategic context -- Document how outcomes align with company strategy, key assumptions about customer needs, and review cadence.