memstack-product-roadmap-builder

name	memstack-product-roadmap-builder
description	Use this skill when the user says 'roadmap', 'product roadmap', 'quarterly plan', 'now/next/later', 'OKRs', or needs strategic planning with themes, milestones, resource allocation, and stakeholder-ready views. Do NOT use for MVP scoping or sprint-level planning.
version	1.0.0
license	Proprietary — MemStack™ Pro by CW Affiliate Investments LLC. See LICENSE.txt

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:

1. Product — what product are you roadmapping?
2. Current state — what's been built? What's the current version?
3. Company goals — what's the business trying to achieve this year?
4. User feedback — what are the top 5 user requests or complaints?
5. Competitive pressure — what are competitors shipping that matters?
6. 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	—	15-20%
Bug fixes / support	[X] devs	—	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)