Roadmap Builder: Building product roadmap...
Creates a strategic product roadmap in Now/Next/Later format with quarterly themes, milestones, dependency mapping, resource allocation, and stakeholder communication templates.
Activation
When this skill activates, output:
Roadmap Builder: Building product roadmap...
Then execute the protocol below.
Context Guard
| Context | Status |
|---|---|
| User says "roadmap", "product roadmap", "quarterly plan" | ACTIVE |
| User says "now/next/later" or "OKRs" | ACTIVE |
| User wants to plan product direction for 3-12 months | ACTIVE |
| User wants to scope an MVP | DORMANT: use MVP Scoper |
| User wants sprint-level stories | DORMANT: use User Story Generator |
Common Mistakes
| Mistake | Why It's Wrong |
|---|---|
| "Roadmap with exact delivery dates" | Dates become promises. Use time horizons (Now/Next/Later) to preserve flexibility. |
| "Feature list disguised as a roadmap" | Roadmaps communicate outcomes and themes, not feature checklists. |
| "One roadmap for everyone" | Engineering, sales, and executives need different views of the same plan. |
| "Plan 12 months in detail" | Detailed plans beyond 3 months are fiction. Be specific for Now, directional for Later. |
| "Set it and forget it" | Roadmaps are living documents. Review and adjust monthly or quarterly. |
Protocol
Step 1: Gather Strategic Context
If the user hasn't provided details, ask:
- Product: what product are you roadmapping?
- Current state: what's been built? What's the current version?
- Company goals: what's the business trying to achieve this year?
- User feedback: what are the top 5 user requests or complaints?
- Competitive pressure: what are competitors shipping that matters?
- Resources: team size, key constraints, upcoming changes?
Step 2: Define Strategic Themes
Themes are the "why" behind your roadmap: outcomes, not features.
Theme template:
markdown### Theme: [Theme Name] **Outcome:** [What success looks like, measurable] **Time horizon:** [Now / Next / Later] **Business driver:** [Revenue / Retention / Acquisition / Efficiency] **Key metric:** [Specific metric this theme moves] **Initiatives under this theme:** 1. [Initiative A, concrete work that delivers on this theme] 2. [Initiative B] 3. [Initiative C]
Example themes (not features):
- "Reduce time-to-first-value" (not "Add onboarding wizard")
- "Expand to mid-market" (not "Build SSO and audit logs")
- "Increase weekly engagement" (not "Add notifications and dashboards")
Recommended: 3-5 themes per quarter. More than 5 means you're spreading too thin.
Step 3: Build Now/Next/Later Roadmap
| Horizon | Timeframe | Certainty | Detail Level |
|---|---|---|---|
| Now | This quarter (0-3 months) | High (committed) | Specific features with milestones |
| Next | Next quarter (3-6 months) | Medium (planned) | Themes and initiatives |
| Later | 6-12 months | Low (exploratory) | Themes and direction only |
Roadmap template:
markdown## Now (Q[X] [Year]): [Quarter Theme] ### Theme 1: [Theme Name] | Initiative | Description | Owner | Target | Status | |-----------|------------|-------|--------|--------| | [Initiative A] | [What it delivers] | [Team/person] | [Month] | [Not started / In progress / Done] | | [Initiative B] | [What it delivers] | [Team/person] | [Month] | [Status] | ### Theme 2: [Theme Name] | Initiative | Description | Owner | Target | Status | |-----------|------------|-------|--------|--------| | [Initiative C] | [What it delivers] | [Team/person] | [Month] | [Status] | --- ## Next (Q[X+1] [Year]): [Quarter Theme] ### Theme 3: [Theme Name] - [Initiative D]: [One-line description] - [Initiative E]: [One-line description] ### Theme 4: [Theme Name] - [Initiative F]: [One-line description] --- ## Later ([Year] H2): [Direction] ### Theme 5: [Theme Name] - [Exploratory direction 1] - [Exploratory direction 2]
Step 4: Map Dependencies
markdown## Dependency Map | Initiative | Depends On | Blocks | Risk Level | |-----------|-----------|--------|-----------| | [Initiative A] | None (can start immediately) | [Initiative C] | Low | | [Initiative B] | [External: design system v2] | None | Medium | | [Initiative C] | [Initiative A] + [API team delivery] | [Initiative E] | High |
Dependency visualization:
Initiative A ──→ Initiative C ──→ Initiative E ↑ Initiative B ─────────┘ (also needs API team delivery) Critical path: A → C → E (any delay cascades)
Dependency rules:
- Highlight the critical path, the longest chain of dependent work
- Flag external dependencies (other teams, vendors, regulatory) as high risk
- If an initiative has 3+ dependencies, consider splitting it or re-sequencing
Step 5: Allocate Resources
Team allocation by theme:
| Theme | Engineering | Design | % of Capacity |
|---|---|---|---|
| [Theme 1] | [X] devs | [X] designers | [X]% |
| [Theme 2] | [X] devs | [X] designers | [X]% |
| Tech debt / maintenance | [X] devs | none | 15-20% |
| Bug fixes / support | [X] devs | none | 10% |
| Total | 100% |
Allocation rules:
- Reserve 15-20% for tech debt (skip this and velocity drops over time)
- Reserve 10% for unplanned bugs and support escalations
- No theme should get less than 20% (or it won't make meaningful progress)
- One team shouldn't work on more than 2 themes simultaneously
Step 6: Define Milestones & OKRs
Quarterly OKRs:
markdown## Q[X] Objectives & Key Results ### Objective 1: [Outcome statement: inspirational but measurable] - KR1: [Metric] from [current] to [target] - KR2: [Metric] from [current] to [target] - KR3: [Metric] from [current] to [target] ### Objective 2: [Outcome statement] - KR1: [Metric] from [current] to [target] - KR2: [Metric] from [current] to [target]
Milestone timeline:
| Milestone | Date | Owner | Definition of Done |
|---|---|---|---|
| [Milestone 1] | [Date] | [Team] | [What "done" means: specific, verifiable] |
| [Milestone 2] | [Date] | [Team] | [Definition of done] |
| [Milestone 3] | [Date] | [Team] | [Definition of done] |
| Quarter review | [End of quarter] | PM | All OKRs scored, next quarter planned |
OKR scoring (end of quarter):
- 0.0-0.3: Failed: significant miss, understand why
- 0.4-0.6: Partial, progress made, needs another quarter
- 0.7-1.0: Success: target met or exceeded
- Sweet spot: 0.7: means targets were ambitious but achievable
Step 7: Create Stakeholder Views
Different audiences need different roadmap views:
Executive view (1 page):
markdown# Product Roadmap, Q[X]-Q[X+2] [Year] ## Vision: [One-line product vision] | Quarter | Theme | Key Deliverable | Business Impact | |---------|-------|----------------|----------------| | Q[X] | [Theme 1] | [Major deliverable] | [Revenue / retention / efficiency] | | Q[X] | [Theme 2] | [Major deliverable] | [Business impact] | | Q[X+1] | [Theme 3] | [Planned direction] | [Expected impact] | | Q[X+2] | [Theme 4] | [Exploratory] | [Potential impact] | **Key risks:** [1-2 biggest risks in plain language] **Resource ask:** [What you need from leadership: headcount, budget, decisions]
Sales/customer view:
markdown# What's Coming: [Product Name] ## Shipping Now (This Quarter) - [Feature/improvement], [Customer benefit in their language] - [Feature/improvement]: [Customer benefit] ## Coming Next - [Planned initiative]: [Customer benefit] - [Planned initiative]: [Customer benefit] ## Exploring - [Direction], we're researching how to [solve X] - [Direction]: early exploration of [area] *Dates and specifics may change. Updated quarterly.*
Engineering view:
markdown# Engineering Roadmap: Q[X] ## Committed Work | Initiative | Epic | Points | Team | Sprint Target | |-----------|------|--------|------|--------------| [Detailed sprint-level breakdown] ## Tech Debt Budget (20%) | Item | Priority | Effort | Impact | |------|----------|--------|--------| [Tech debt items with priority] ## Architecture Decisions Needed - [Decision 1: by when, who decides] - [Decision 2: by when, who decides]
Output Format
markdown# Product Roadmap: [Product Name] ## Strategic Context - **Vision:** [One-line vision] - **Annual goal:** [Primary business goal] - **Planning period:** Q[X]: Q[X+2] [Year] - **Team size:** [X engineers, X designers] ## Themes [From Step 2, 3-5 themes with outcomes] ## Now/Next/Later Roadmap [From Step 3: detailed Now, directional Next, thematic Later] ## Dependencies [From Step 4, dependency map with critical path] ## Resource Allocation [From Step 5: team allocation by theme] ## OKRs & Milestones [From Step 6, quarterly OKRs with milestone timeline] ## Stakeholder Views ### Executive Summary [1-page executive view] ### Customer-Facing Roadmap [What's Coming view]
Completion
Roadmap Builder: Complete! Planning horizon: [X quarters] Themes: [Count] Now initiatives: [Count] (committed) Next initiatives: [Count] (planned) Later directions: [Count] (exploratory) OKRs: [Count] objectives, [Count] key results Stakeholder views: 3 (executive, customer, engineering) Next steps: 1. Review with engineering leads for feasibility 2. Present executive view to leadership for alignment 3. Publish customer-facing roadmap 4. Schedule monthly roadmap review checkpoints 5. Score OKRs at end of quarter and plan next
Level History
- Lv.1: Base: Strategic theme definition (outcome-based, not feature-based), Now/Next/Later roadmap format with certainty levels, dependency mapping with critical path, resource allocation with tech debt/bug budget, quarterly OKRs with scoring guide, milestone timeline, 3 stakeholder views (executive, customer, engineering). (Origin: MemStack Pro v3.2, Mar 2026)
