roadmap-planning

Key Concepts

What is Strategic Roadmap Planning?

Roadmap planning is the process of:

1. Gathering inputs — Customer problems, business goals, technical constraints
2. Defining initiatives — Epics with clear hypotheses and success metrics
3. Prioritizing — Rank initiatives by impact, effort, strategic fit
4. Sequencing — Organize into releases/quarters with logical dependencies
5. Communicating — Present roadmap to stakeholders with strategic narrative

For roadmap type descriptions (Now/Next/Later, Theme-Based, Timeline, Feature-List anti-pattern) and the rationale for this approach, see references/roadmap-types.md.

Anti-Patterns (What This Is NOT)

• Not a commitment: Roadmaps are strategic plans, not contracts
• Not a feature list: Roadmaps frame problems, not just solutions
• Not waterfall: Roadmaps evolve quarterly based on learning

When to Use This

• Annual or quarterly planning cycles
• After product strategy session (translate strategy to roadmap)
• Onboarding new stakeholders (align on direction)
• Reframing existing roadmap (shift from feature-driven to outcome-driven)

When NOT to Use This

• For tactical sprint planning (use backlog instead)
• When strategy is unclear (run product-strategy-session first)
• When stakeholders expect date commitments (address expectations first)

---

Facilitation Source of Truth

When running this workflow as a guided conversation, use workshop-facilitation as the interaction protocol and delegate to agents/roadmap-coordinator.md for entry mode selection, Phase 1 intake question sequence, sub-skill handoff triggers, and loop-back conditions.

---

Application

Use template.md for the full fill-in structure.

This workflow orchestrates 5 phases over 1-2 weeks, using multiple component and interactive skills.

---

Phase 1: Gather Inputs (Day 1-2)

Goal: Collect business goals, customer problems, technical constraints, stakeholder requests.

The four input-gathering activities below are fully independent — collect them concurrently to reduce elapsed time.

Activities

1. Review Business Goals (OKRs, Strategic Initiatives)

• Source: Company OKRs, exec strategy memos, board decks
• Output: 3-5 business outcomes to optimize for

2. Review Customer Problems (Discovery Insights)

• Source: Discovery interviews, support tickets, NPS feedback, churn surveys
• Use: Insights from skills/discovery-process/SKILL.md (if recently completed)
• Output: 3-5 validated customer problems

3. Review Technical Constraints & Opportunities

• Source: Engineering leadership, tech debt assessments
• Output: List of technical investments required

4. Review Stakeholder Requests

• Source: Sales, marketing, customer success, execs
• Output: List of stakeholder requests (not yet committed)

Outputs from Phase 1

• Business outcomes: 3-5 OKRs or strategic goals
• Customer problems: 3-5 validated pain points
• Technical investments: Platform/tech debt items
• Stakeholder requests: Feature requests from internal teams

---

Phase 2: Define Initiatives (Epics) (Day 3-4)

Goal: Turn inputs into epics with hypotheses, success metrics, and effort estimates.

Activities

1. Define Epic Hypotheses

• Use: skills/epic-hypothesis/SKILL.md (component)
• Format: "We believe that [building X] for [persona] will achieve [outcome] because [assumption]."
• Output: 10-15 epic hypotheses

See examples/sample.md — Example 3 for sample epic hypotheses

2. Estimate Effort (T-Shirt Sizing)

• S: 1-2 weeks (1-2 engineers)
• M: 3-4 weeks (2-3 engineers)
• L: 2-3 months (3-5 engineers)
• XL: 3+ months (5+ engineers)
• Output: Effort estimate per epic

3. Map to Business Outcomes

• Tag each epic with primary business outcome (Retention, Acquisition, Engagement, etc.)

Outputs from Phase 2

• 10-15 epics: Each with hypothesis, success metric, effort estimate
• Business outcome mapping: Which epics drive which OKRs

---

Phase 3: Prioritize Initiatives (Day 5)

Goal: Rank epics by impact, effort, and strategic fit.

Activities

1. Choose Prioritization Framework

• Use: skills/prioritization-advisor/SKILL.md (interactive)
• Output: Recommended framework (RICE, ICE, Value/Effort, etc.)

2. Score Epics

• Apply framework to all epics
• See examples/sample.md — Example 4 for a RICE scoring table

3. Adjust for Strategic Fit

• Review scores against business goals
• For any epic flagged for a potential strategic override: use the think tool to reason through the trade-off between RICE rank and strategic bet value before committing to the final ranked list. Surface the reasoning before presenting the output.

Outputs from Phase 3

• Ranked backlog: Epics sorted by priority (RICE score + strategic adjustments)
• Top 10 epics: Highest-priority initiatives for roadmap

---

Phase 4: Sequence Roadmap (Day 6-7)

Goal: Organize epics into quarters/releases with logical dependencies.

Activities

1. Map Dependencies

• When the epic count exceeds 8, use sequential thinking to enumerate all epic pairs, check each pair for directional dependency, and produce a topologically sorted sequence before assigning epics to quarters.
• Output: Dependency graph (Epic A → Epic B → Epic C)

2. Sequence by Quarter (or Release)

• Now (Q1): Top 3-5 epics, no dependencies
• Next (Q2): Next 3-5 epics, may depend on Q1 completion
• Later (Q3+): Remaining epics, lower confidence

See examples/sample.md — Example 5 for quarterly and Now/Next/Later roadmap formats

3. Validate with Engineering

• Confirm sequencing is realistic (capacity, dependencies, hidden technical blockers)
• Output: Validated roadmap sequence

Outputs from Phase 4

• Sequenced roadmap: Epics organized by Q1, Q2, Q3
• Dependency map: What depends on what
• Capacity check: Engineering agrees sequence is feasible

---

Phase 5: Communicate Roadmap (Week 2)

Goal: Present roadmap to stakeholders, gather feedback, build alignment.

Activities

1. Create Roadmap Presentation

• Structure:
  • Slide 1: Strategic context (business goals, customer problems)
  • Slides 2-3: Roadmap overview (Q1, Q2, Q3)
  • Slides 4-6: Deep dive per quarter (epics, hypotheses, success metrics)
  • Slide 7: What's NOT on roadmap (and why)
  • Slide 8: Dependencies and risks
• Duration: 2-3 hours to prepare

2. Present to Stakeholders

• Audience: Execs, product leadership, engineering, sales, marketing, CS
• Focus: Strategic narrative, outcome focus, flexibility framing

3. Gather Feedback and Refine

• Key questions: Do priorities align with business goals? Are we missing critical customer problems? Are dependencies clear?
• Based on feedback: Adjust priorities, add missing epics, clarify dependencies
• Output: Final roadmap v1.0

4. Publish Roadmap

• Internal: Confluence, Notion, Productboard, etc.
• External (Optional): Now/Next/Later format for customers

Outputs from Phase 5

• Roadmap presentation: 30-45 min deck
• Stakeholder alignment: Feedback incorporated, concerns addressed
• Published roadmap: Accessible to team or customers

---

Examples

See examples/sample.md for full roadmap examples including good vs. bad roadmap comparison, epic hypotheses, RICE scoring, and quarterly sequencing.

---

References

Related Skills (Orchestrated by This Workflow)

Phase 2:

• skills/epic-hypothesis/SKILL.md (component)

Phase 3:

• skills/prioritization-advisor/SKILL.md (interactive)

Optional/Related:

• skills/product-strategy-session/SKILL.md (workflow) — Run before roadmap planning to establish strategy
• skills/discovery-process/SKILL.md (workflow) — Provides customer problem inputs for Phase 1
• skills/user-story-mapping-workshop/SKILL.md (interactive) — For complex epics requiring release planning

Anti-Patterns

See references/anti-patterns.md for symptom/consequence/fix detail on each roadmap pitfall.

Roadmap Types

See references/roadmap-types.md for descriptions of Now/Next/Later, Theme-Based, Timeline, and Feature-Based roadmap formats.

External Frameworks

• Bruce McCarthy, Product Roadmaps Relaunched (2017) — Outcome-driven roadmaps
• C. Todd Lombardo, Product Roadmaps Relaunched (2017) — Now/Next/Later framework
• Intercom, "RICE Prioritization" (2016) — Prioritization framework