Prioritizing Roadmap

Scope

Covers

• Turning messy roadmap inputs into a ranked opportunity list + coherent roadmap
• Defining a planning “season” (macro context) and success criteria
• Using a common-currency scoring model (ICE + assumptions) to compare across teams
• Producing an alignment-ready Roadmap Prioritization Pack

When to use

• “What should we build next?”
• “We need a Q2/Q3 roadmap.”
• “We have too many requests and no way to compare them.”
• “We need to prioritize across multiple teams/pods.”

When NOT to use

• You don’t have any agreed goal / North Star / strategic intent (do product vision / goals first; use setting-okrs-goals).
• You need sprint planning or story-level estimation (use your agile/scrum process).
• You’re only choosing a single experiment within an already-fixed roadmap.
• You need a full customer discovery plan from scratch (use problem-definition).
• You need to cut scope within an already-committed project (use scoping-cutting).
• You need an engineering/technical roadmap for infrastructure or platform work (use technical-roadmaps).
• You need to track milestones, deadlines, and delivery status on an existing plan (use managing-timelines).

Inputs

Minimum required

• Product + primary customer segment
• Planning horizon + cadence (e.g., next 6 weeks, next quarter, rolling 12–24 months)
• Success criteria (North Star / business goal) + 2–5 guardrails
• Candidate opportunities (or current roadmap/backlog) with rough size/effort
• Constraints: capacity, commitments, dependencies, deadlines, risk tolerance

Missing-info strategy

• Ask up to 5 questions from references/INTAKE.md.
• If still missing, proceed with clearly labeled assumptions and provide 2–3 roadmap options.

Outputs (deliverables)

Produce a Roadmap Prioritization Pack in Markdown (in-chat; or as files if requested):

1. Context snapshot (goal, horizon, constraints, stakeholders)
2. Season framing (what changed, key bets, explicit non-goals)
3. Opportunity inventory with conviction level (known vs hypothesis) and evidence
4. Prioritization model (common currency + ICE scoring + assumptions)
5. Ranked opportunity list (top 10–20) + “parking lot”
6. Roadmap draft (Now/Next/Later or quarterly themes) + update cadence (rolling plan)
7. Decision narrative (why these, why now) + “Think Bigger” ideas
8. Risks / Open questions / Next steps (always included)

Templates: references/TEMPLATES.md

Workflow (8 steps)

1) Intake + decision framing

• Inputs: User context; references/INTAKE.md.
• Actions: Confirm the decision (backlog vs quarterly roadmap vs annual planning), horizon, stakeholders, constraints, and “must-do” commitments.
• Outputs: Context snapshot.
• Checks: Everyone agrees what decision will be made and by when.

2) Define the “season” + success criteria

• Inputs: Context snapshot.
• Actions: Name the current season (macro context), define 3–5 season bets, and set success criteria (North Star + guardrails).
• Outputs: Season framing section.
• Checks: A stakeholder can restate “why now” and “what we’re optimizing for”.

3) Build the opportunity inventory (separate truth vs hypotheses)

• Inputs: Candidate inputs (requests, ideas, problems).
• Actions: Normalize each item into a problem/outcome statement; tag conviction level (Known / Belief / Hypothesis) and evidence; split discovery vs delivery.
• Outputs: Opportunity inventory table.
• Checks: Every item has an intended outcome metric and a confidence/evidence note.

4) Define the common-currency scoring model (ICE + assumptions)

• Inputs: Inventory + success criteria.
• Actions: Choose a primary “common currency” (e.g., North Star units, revenue, cost, risk reduction) and define ICE scales; estimate impact ranges and confidence based on evidence.
• Outputs: Scoring model + filled scoring table.
• Checks: Two people using the same scales would produce similar relative rankings.

5) Stress-test the ranking (scenarios + constraints)

• Inputs: Scored list + constraints.
• Actions: Apply constraints (capacity, dependencies, deadlines); run 2–3 scenarios (base / aggressive / conservative); ensure a balanced portfolio (core, growth, quality, big bets).
• Outputs: Shortlist (top set) + parking lot + key tradeoffs.
• Checks: Tradeoffs and “no’s” are explicit; nothing critical is missing.

6) Draft the roadmap (sequencing + cadence)

• Inputs: Shortlist + scenario choice.
• Actions: Convert priorities into a roadmap (Now/Next/Later or quarterly themes), sequencing by dependencies and learning; define a rolling plan cadence (e.g., rolling 12–24 months, refreshed every 6 months).
• Outputs: Roadmap draft + update cadence.
• Checks: The roadmap is coherent, feasible, and resilient to new inputs.

7) Write the decision narrative + alignment plan

• Inputs: Roadmap draft + rationale.
• Actions: Write “why these, why now”; include a “Think Bigger” section; define how the roadmap will be communicated and updated.
• Outputs: Decision narrative + comms/rollout plan.
• Checks: A cross-functional partner can explain the roadmap without you in the room.

8) Quality gate + finalize the pack

• Inputs: Full draft pack.
• Actions: Run references/CHECKLISTS.md and score with references/RUBRIC.md. Add Risks/Open questions/Next steps.
• Outputs: Final Roadmap Prioritization Pack.
• Checks: Pack is shareable as-is; assumptions, owners, and cadence are explicit.

Quality gate (required)

• Use references/CHECKLISTS.md and references/RUBRIC.md.
• Always include: Risks, Open questions, Next steps.

Examples

Example 1 (B2B SaaS): “Prioritize our next-quarter roadmap for a collaboration product across Growth + Core.”
Expected: season framing, scored opportunity inventory, a Now/Next/Later roadmap, and a clear decision narrative with explicit non-goals.

Example 2 (Marketplace): “Prioritize 6 months of roadmap across supply, demand, and trust & safety.”
Expected: a common-currency model that makes cross-team tradeoffs comparable and a rolling plan refreshed on a fixed cadence.

Boundary example 1: “Give me a 2-year roadmap, we don’t have goals or constraints.” Response: ask for goals/constraints; if unavailable, produce options + assumptions and recommend doing product vision + North Star first.

Boundary example 2: “We already have the roadmap locked -- help me cut scope on the authentication project to hit the deadline.” Response: redirect to scoping-cutting. This skill is for deciding what goes on the roadmap, not for trimming scope within a committed project.

Anti-patterns (common failure modes)

1. HiPPO-driven ranking -- Using a scoring model but overriding it with the highest-paid person’s opinion without documenting the override rationale. If a score is overridden, the decision narrative must state why and what assumption changed.
2. Score-as-truth -- Treating ICE scores as precise measurements instead of rough relative signals. Two items scored 7.2 vs 7.0 are not meaningfully different. The model produces tiers, not a total order.
3. Missing the status quo option -- Ranking only new features without including “do nothing / invest in quality / pay down debt” as a scored alternative. The opportunity cost of not improving the existing product must be visible.
4. Roadmap-as-promise -- Presenting a prioritized roadmap as a commitment with dates rather than a rolling plan with update cadence. A good roadmap is a living document with explicit refresh triggers.
5. Invisible non-goals -- Producing a “yes” list without a corresponding “parking lot” and explicit “we chose not to do X because Y.” Stakeholders whose items were deprioritized need to see the rationale, not just the absence of their request.