Roadmap Builder

🗺️ Roadmap Builder — Strategic Product Roadmap

Create a now/next/later roadmap with quarterly milestones, resource allocation, and stakeholder-ready presentation.

Activation

When this skill activates, output:

🗺️ Roadmap Builder — Planning your product roadmap...

Protocol

Step 1: Gather Inputs

Ask the user for:

• Product vision: Where is this product going in 12-18 months?
• Current state: What exists today? What stage? (MVP, growth, mature)
• Team capacity: How many engineers/designers? Full-time or part-time?
• Time horizon: 3 months, 6 months, or 12 months?
• Key constraints: Technical debt, platform migrations, compliance deadlines?
• Stakeholder priorities: What does leadership/board care most about?

Step 2: Define Themes/Pillars

Organize the roadmap around 3-5 strategic themes:

Each theme should tie directly to a business metric. No theme exists "because it's interesting."

Step 3: Map Features to Themes

For each proposed feature:

Priority scoring formula:

• Impact (1-5): How much does this move the theme's metric?
• Confidence (1-5): How sure are we this will work?
• Effort (1-5, inverted): How easy is it to build? (5 = trivial)
• Score = (Impact × Confidence) / Effort

Rank by score. Top items go to "Now."

Step 4: Quarterly Milestones

Break the time horizon into quarters with concrete deliverables:

━━━ Q1: [Quarter Name/Theme] ━━━━━━━━━━━━━
Objective: [what we aim to achieve]
Key Result: [measurable outcome]

Deliverables:
  • [Feature A] — [owner] — [est. weeks]
  • [Feature B] — [owner] — [est. weeks]
  • [Infrastructure work] — [owner] — [est. weeks]

Milestone: By end of Q1, [concrete achievement].

━━━ Q2: [Quarter Name/Theme] ━━━━━━━━━━━━━
Objective: [what we aim to achieve]
Key Result: [measurable outcome]

Deliverables:
  • [Feature C] — [owner] — [est. weeks]
  • [Feature D] — [owner] — [est. weeks]

Milestone: By end of Q2, [concrete achievement].

━━━ Q3-Q4: [Horizon Planning] ━━━━━━━━━━━━
[Less detailed, more directional]

Rule: Q1 is detailed, Q2 is planned, Q3+ is directional. Don't fake precision for the future.

Step 5: Dependencies & Sequencing

Map what blocks what:

DEPENDENCY GRAPH:
  [Feature A] ──→ [Feature C] (needs A's data model)
  [Platform work] ──→ [Feature B] (needs new infra)
  [Feature D] ──→ [Feature E] (iterates on D's feedback)

CRITICAL PATH:
  [Platform] → [Feature A] → [Feature C] → [Feature E]
  Duration: ~[X] weeks
  Risk: If platform work slips, everything shifts.

Identify the critical path — the longest chain of dependent work. This determines your actual timeline.

Step 6: Resource Allocation

Map team capacity to milestones:

── TEAM ALLOCATION ────────────────────────

Q1:
  Engineer 1: Feature A (6 weeks) → Feature B (4 weeks)
  Engineer 2: Platform work (8 weeks) → Bug fixes (2 weeks)
  Designer:   Feature A design (3 weeks) → Feature C design (3 weeks)

Q2:
  Engineer 1: Feature C (6 weeks) → Feature D (4 weeks)
  Engineer 2: Feature D (6 weeks) → Tech debt (4 weeks)
  Designer:   Feature D design (4 weeks) → User research (6 weeks)

Capacity rules:

• Plan to 70-80% capacity (leave room for bugs, support, unexpected work)
• No person on more than 2 projects per quarter
• Design should lead engineering by 2-4 weeks
• Include dedicated time for tech debt (15-20% of capacity)

Step 7: Risk Flags & Contingencies

For each high-impact risk, define a trigger (how you'll know it's happening) and action (what you'll do).

Step 8: Stakeholder Communication Format

Present the roadmap in Now/Next/Later view for non-technical stakeholders:

━━━ PRODUCT ROADMAP ━━━━━━━━━━━━━━━━━━━━━━

🟢 NOW (This Quarter)
  Committed. In progress or starting soon.
  ├── [Feature A]: [one-line benefit to users]
  ├── [Feature B]: [one-line benefit to users]
  └── [Platform]: [one-line benefit — why it matters]

🟡 NEXT (Next Quarter)
  Planned. High confidence, may shift in scope.
  ├── [Feature C]: [one-line benefit]
  ├── [Feature D]: [one-line benefit]
  └── [Research]: [what we're exploring]

🔵 LATER (Future)
  Directional. Subject to change based on learnings.
  ├── [Feature E]: [one-line vision]
  ├── [Expansion]: [one-line vision]
  └── [Big bet]: [one-line vision]

Communication rules:

• NOW = commitments (don't include anything you might cut)
• NEXT = plans (signal that scope might change)
• LATER = direction (explicitly say "subject to change")
• Never put dates on LATER items
• Update this view monthly at minimum

Step 9: Output

Present both views:

━━━ PRODUCT ROADMAP: [Product Name] ━━━━━━━
Vision: [one sentence]
Horizon: [X months]
Team: [X engineers, X designers]

── STAKEHOLDER VIEW (Now/Next/Later) ──────
[Now/Next/Later format from Step 8]

── DETAILED QUARTERLY PLAN ────────────────
Q1: [deliverables, owners, milestones]
Q2: [deliverables, owners, milestones]
Q3+: [directional themes]

── THEMES & METRICS ───────────────────────
[theme table with target metrics]

── DEPENDENCIES ───────────────────────────
[dependency graph + critical path]

── RESOURCE ALLOCATION ────────────────────
[team allocation by quarter]

── RISKS ──────────────────────────────────
[risk table with triggers and contingencies]

Inputs

• Product vision (12-18 month)
• Current state and stage
• Team capacity
• Time horizon
• Key constraints and stakeholder priorities

Outputs

• 3-5 strategic themes tied to business metrics
• Feature-to-theme mapping with priority scores
• Quarterly milestones with deliverables and owners
• Dependency graph with critical path identification
• Resource allocation plan at 70-80% capacity
• Risk flags with triggers and contingency actions
• Now/Next/Later stakeholder-ready view
• Detailed quarterly breakdown

Level History

• Lv.1 — Base: Theme-driven roadmap with ICE priority scoring, quarterly milestone planning, dependency graphing with critical path, resource allocation at 70-80% capacity, Now/Next/Later stakeholder format, risk flags with triggers and contingencies. Dual output: stakeholder view + detailed plan. (Origin: MemStack v3.2, Mar 2026)