cwinvestments 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:
### 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:
## 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
## 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:
## 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):
# 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:
# 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:
# 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
# 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)