Roadmap Planning
Build an outcome-driven roadmap across 5 phases (gather inputs → define epics → prioritize → sequence → communicate) with hypotheses, RICE scores, and stakeholder alignment.
Your roadmap is a list of features grouped by quarter. Engineering builds them. Nothing moves on the OKRs. That's not a roadmap — it's a wishlist with dates. A real roadmap connects each epic to a hypothesis, a business outcome, and a metric — and shows execs why X was prioritized over Y. Then survives the first stakeholder challenge.
Who it's for: PMs running quarterly/annual planning, product leads sequencing across teams, founders translating strategy into execution, exec teams demanding outcome-driven roadmaps
Example
"Plan our Q1-Q3 roadmap from 15 competing initiatives" → Phase 1 inputs (3 OKRs, 4 customer problems) → Phase 2 (10 epics with hypotheses + RICE) → Phase 3 (top 10 ranked) → Phase 4 (Now/Next/Later sequenced) → Phase 5 (45-min exec presentation + refinements)
New here? 3-minute setup guide → | Already set up? Copy the template below.
# Roadmap Planning
Plan a strategic roadmap across prioritization, epic definition, stakeholder alignment, and sequencing. Move from disconnected feature requests to a cohesive, outcome-driven roadmap that aligns stakeholders and sequences work logically.
Not a Gantt chart. A strategic communication tool showing what you're building, why it matters, and how it ladders to business outcomes.
## Types of Roadmaps
**Now/Next/Later** — agile teams, uncertainty, continuous discovery
**Theme-Based** — exec communication, strategic intent
**Timeline (Quarters)** — resource planning, stakeholder communication
**Feature-Based (anti-pattern)** — lists features without strategic narrative
## Why This Works
- **Outcome-driven** — ties initiatives to business/customer outcomes
- **Stakeholder alignment** — transparent process reduces political friction
- **Strategic clarity** — shows "why," not just "what"
- **Flexible** — adapts as you learn
**Anti-patterns:** Not a commitment. Not a feature list. Not waterfall.
## When to Use
**Use:** Annual/quarterly planning, after strategy session, onboarding stakeholders, reframing feature-driven roadmaps.
**Don't use:** Sprint planning, when strategy is unclear, when stakeholders expect date commitments.
## The 5 Phases (1-2 weeks)
### Phase 1: Gather Inputs (Day 1-2)
- **Business goals** — OKRs, exec memos, board decks → 3-5 outcomes
- **Customer problems** — discovery insights, tickets, NPS, churn → 3-5 validated pains
- **Technical constraints** — eng leadership input → tech debt, migrations
- **Stakeholder requests** — sales, marketing, CS → uncommitted requests
### Phase 2: Define Initiatives (Day 3-4)
- `epic-hypothesis` — 60 min per epic → 10-15 epic hypotheses
- T-shirt sizing (S=1-2wk / M=3-4wk / L=2-3mo / XL=3+mo) — PM + eng lead
- Map to business outcomes (Retention, Acquisition, Engagement, etc.)
### Phase 3: Prioritize (Day 5)
- `prioritization-advisor` — choose framework
- Score epics — PM + eng + leadership
- Adjust for strategic fit (override scores when strategic)
Example RICE:
| Epic | Reach | Impact | Conf | Effort | RICE |
|------|-------|--------|------|--------|------|
| Onboarding | 10K | 3 | 80% | 1mo | 24K |
| Enterprise SSO | 500 | 3 | 90% | 2mo | 675 |
### Phase 4: Sequence (Day 6-7)
- Map dependencies
- Sequence by quarter or Now/Next/Later
- Validate capacity with engineering
```
Q1 (Now): Onboarding, SSO, Mobile
Q2 (Next): Reporting, Slack, Pricing
Q3 (Later): Mobile App, AI, i18n
```
### Phase 5: Communicate (Week 2)
Presentation: strategic context → roadmap overview → quarter deep dives → what's NOT on roadmap → dependencies/risks.
Audience: execs, leadership, eng, sales, marketing, CS. 45 min present + 15 Q&A.
Refine based on feedback (1-2 days). Publish internally; optionally externally (Now/Next/Later).
## Time Investment
- **Fast track:** 1 week (existing epics, quick alignment)
- **Typical:** 1.5-2 weeks (define epics + stakeholder review)
## Common Pitfalls
1. **Feature-driven roadmap** → frame epics as hypotheses with metrics
2. **HiPPO prioritization** → use RICE/ICE for transparency
3. **Roadmap as commitment** → "strategic plan, subject to change"
4. **No dependencies mapped** → explicit Phase 4 with eng validation
5. **Solo PM roadmap** → gather inputs in Phase 1, draft review in Phase 5
## References
- `epic-hypothesis` (Phase 2)
- `prioritization-advisor` (Phase 3)
- `product-strategy-session` (run before)
- `discovery-process` (Phase 1 inputs)
- `user-story-mapping-workshop` (complex epics)
**External:**
- Bruce McCarthy & C. Todd Lombardo, *Product Roadmaps Relaunched* (2017)
- Intercom, *RICE Prioritization* (2016)
What This Does
Orchestrates 5 phases (inputs → epics → prioritize → sequence → communicate) over 1-2 weeks. Each epic gets a hypothesis, success metric, effort estimate, and business-outcome tag. RICE scoring, dependency mapping, and stakeholder alignment built in.
Pairs with epic-hypothesis, prioritization-advisor, product-strategy-session, and discovery-process.
Quick Start
mkdir -p ~/Documents/RoadmapPlanning
mv ~/Downloads/CLAUDE.md ~/Documents/RoadmapPlanning/
cd ~/Documents/RoadmapPlanning
claude
Provide OKRs, validated customer problems, technical constraints, and stakeholder requests. Claude orchestrates the 5 phases and produces a published roadmap.
The 5 Phases
| Phase | Time | Output |
|---|---|---|
| 1. Gather Inputs | Day 1-2 | OKRs + problems + tech + stakeholder requests |
| 2. Define Initiatives | Day 3-4 | 10-15 epic hypotheses with effort + outcome tags |
| 3. Prioritize | Day 5 | RICE-ranked top 10 epics |
| 4. Sequence | Day 6-7 | Now/Next/Later or Q1/Q2/Q3 with dependencies |
| 5. Communicate | Week 2 | Presentation + feedback + published roadmap |
Tips & Best Practices
- Frame epics as hypotheses, not features. "Guided onboarding will increase activation 40%→60%" beats "build onboarding checklist."
- Tag every epic with a business outcome. If it doesn't ladder to an OKR, question it.
- Strategic overrides are okay. RICE is input, not output — Enterprise SSO might score lower but matter more.
- Communicate flexibility. "Subject to change based on learning" prevents commitment-vs-plan confusion.
- What's NOT on the roadmap matters. Stakeholders trust you more when you explicitly name what didn't make the cut and why.
Common Pitfalls
- Feature list with no hypothesis or success metric
- HiPPO prioritization (no transparent framework)
- Roadmap treated as a contract instead of a plan
- No dependency mapping → Q2 work blocked by Q1 slippage
- Solo PM creates roadmap and presents it as finished