/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 | 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 simultaneo