roadmapping

Roadmapping

Create and maintain outcome-based product roadmaps using Now/Next/Later format. Define OKRs that connect work to business outcomes.

Announce at start: "I'm using the roadmapping skill to [create/update] the product roadmap."

Checklist

You MUST create a task for each of these items and complete them in order:

1. Define product vision and strategic themes — What direction are we heading?
2. Define OKRs — Objectives with 3-5 Key Results each
3. Map initiatives to outcomes — What work drives which outcomes?
4. Position in Now/Next/Later — Time-horizon buckets with confidence levels
5. Identify dependencies — What must happen before what?
6. Define communication plan — Who needs to know what, when?
7. Define review cadence — How often does this get updated?
8. Save and present — Document for sharing

Step 1: Define Product Vision and Strategic Themes

Product Vision

The aspirational future state you're working toward. Long-term, inspirational, stable.

Format:

[Product name] helps [target user] achieve [key benefit] by [unique approach].

Examples:

• Airbnb: "Belong anywhere."
• Slack: "Make work life simpler, more pleasant, and more productive."
• Stripe: "Increase the GDP of the internet."

Strategic Themes

3-5 broad areas of investment that support the vision. Themes persist across multiple quarters.

Theme	What it means	Why it matters
User Activation	Help new users reach their first "aha moment" faster	Activation is the biggest lever for retention
Collaboration	Make it effortless for teams to work together	Team accounts have 3x higher LTV
Platform Reliability	Improve uptime, performance, and error handling	Trust is eroding with current 99.5% uptime

Step 2: Define OKRs

Objective

A qualitative, inspirational goal. "Where do we want to go?"

• Written as a single sentence
• Aspirational but achievable
• Time-bound (typically quarterly)

Examples:

• "Become the easiest-to-use project management tool for small teams"
• "Make our API the preferred integration platform for e-commerce"
• "Create a product that users love to tell their friends about"

Key Results

3-5 quantitative, measurable outcomes that show progress toward the Objective.

Format:

[Improve/Move/Change] [metric] from [baseline] to [target] by [timeframe]

Examples:

• "Increase new user activation rate from 40% to 65% by end of Q3"
• "Reduce median time-to-first-project from 12 minutes to 3 minutes"
• "Achieve NPS of 50+ (currently 32) by end of Q4"
• "Grow weekly active teams from 500 to 1,200 by end of Q3"

OKR Best Practices

• KRs must be outcomes, not outputs ("reduce churn to 2%" not "ship retention emails")
• 3-5 KRs per Objective (more dilutes focus)
• 60-70% achievement is the sweet spot (100% means they were too easy)
• Separate committed OKRs (must deliver) from aspirational OKRs (stretch goals)
• Every team's OKRs should connect to company-level OKRs

Alternatives

• North Star Metric — Single metric that captures core value. Use as a complement to OKRs.
• KPIs — Broader performance indicators for ongoing health monitoring.

Step 3: Map Initiatives to Outcomes

For each initiative in your roadmap, answer: which outcome does this drive?

Initiative	Drives which KR(s)?	Confidence
Redesigned onboarding flow	KR1: Activation rate	High (backed by user testing)
Team invite improvements	KR4: Weekly active teams	Medium
Performance optimization	KR3: NPS improvement	Low (indirect relationship)

Initiatives that don't connect to any outcome should be questioned. Every significant piece of work should trace back to a strategic goal.

Step 4: Now/Next/Later

Use relative time buckets instead of fixed dates:

Now

• Actively working on or starting this month/quarter
• High confidence in scope and outcome
• Features are specified, designs are done
• Dependencies are resolved

Next

• Up next in the queue (next quarter or two)
• Medium confidence — scope is clear but details may shift
• Some discovery may still be needed
• Priority order matters

Later

• Future initiatives (2-4 quarters out or beyond)
• Low confidence — broad strokes, subject to change
• Discovery not yet done
• Order is rough; things will shift

Example Roadmap

Now	Next	Later
Redesigned onboarding flow	Team collaboration features	Mobile app
Performance optimization (P95 < 2s)	Advanced analytics dashboard	AI-powered recommendations
SSO integration (Enterprise)	Public API v2	Internationalization
Bug fix sprint (top 20 issues)	Dark mode	Marketplace / integrations

Confidence Levels

For each item, indicate confidence:

• High: We know what to build and why. Validated with users.
• Medium: General direction is clear. Some unknowns remain.
• Low: Hypothesis stage. Needs discovery and validation.

External roadmaps (customer-facing) should only include High and some Medium confidence items.

Step 5: Identify Dependencies

Map what must happen before what:

Initiative A (onboarding redesign) → depends on → Design system v2
Initiative B (team features) → depends on → Initiative A (enables team invites)
Initiative C (API v2) → no dependencies → can start anytime

Flag:

• Blocking dependencies: Can't start without this being done
• Enabling dependencies: Can start, but full value requires this
• Cross-team dependencies: Requires another team's work

Step 6: Communication Plan

Different stakeholders need different views:

Stakeholder	Needs	Format	Cadence
Executive team	Strategic alignment, resource decisions, key risks	Executive summary + Now/Next/Later	Monthly
Engineering	What's coming, dependency resolution, technical context	Full roadmap + sprint plans	Bi-weekly
Design	Upcoming design needs, user insights	Thematic view + discovery queue	Weekly
Sales/Marketing	Launch timing, competitive positioning, customer commitments	External roadmap (conservative)	Monthly
Customer Success	Feature changes, training needs, support impact	Feature-focused view	Per release
Customers	What's coming, why, when (roughly)	Public roadmap (high confidence only)	Quarterly

Step 7: Review Cadence

A roadmap is a living document. Define how often it gets reviewed:

• Weekly: PM review — any blockers? New information?
• Monthly: Team review — adjust priorities, update confidence levels
• Quarterly: Strategic review — major reprioritization, new OKRs
• On-demand: When a significant event changes priorities (competitor launch, market shift, major customer win/loss)

Document Format

Save to: docs/product-superpowers/roadmaps/YYYY-QN-roadmap.md

# Product Roadmap — [Product Name] [Time Period]

**Last Updated:** YYYY-MM-DD
**Vision:** [One sentence]
**Status:** Draft / In Review / Approved

## Strategic Themes
| Theme | Meaning | Importance |
|-------|---------|------------|
| ... | ... | ... |

## OKRs
**Objective 1:** [Qualitative goal]
- KR1: [Metric] from [baseline] to [target] by [timeframe]
- KR2: ...
- KR3: ...

## Roadmap
| Now (Q1 2026) | Next (Q2-Q3) | Later (Q4+) |
|---------------|--------------|-------------|
| Initiative A (High confidence) | Initiative D (Medium) | Initiative G (Low) |
| Initiative B (High confidence) | Initiative E (Medium) | Initiative H (Low) |
| Initiative C (Medium confidence) | Initiative F (Low) | Initiative I (Low) |

## Dependencies
...

## Risks and Mitigations
...

## Review Cadence
...

Key Principles

• Outcome over output — The roadmap says WHAT we want to achieve, not exactly what we'll build
• Confidence over precision — "High confidence Q2" is better than "April 15" when you're guessing
• Now/Next/Later over dates — Avoid false precision. Use relative buckets.
• Transparent uncertainty — Be explicit about what you don't know
• Living document — Update at least monthly. A stale roadmap is worse than no roadmap.
• Connect everything to outcomes — If an initiative doesn't drive a KR, ask why it's on the roadmap

Common Mistakes

• Feature-based roadmaps — Listing features with dates ("Login page by March 15"). Outcome-based is better.
• False precision — Committing to dates 9 months out with low confidence
• Everything is "Now" — If everything is a priority, nothing is
• Roadmap as a promise — It's a directional plan, not a contract
• No stakeholder differentiation — Showing the same detailed view to executives and engineers
• Stale roadmaps — Not updated for 6+ months but still referenced
• Pet features — Items on the roadmap because someone important asked, not because they drive outcomes

Key References

• "Product Roadmaps Relaunched" by C. Todd Lombardo et al.
• "Outcomes Over Output" by Josh Seiden
• "Measure What Matters" by John Doerr (OKRs)
• "Inspired" by Marty Cagan (roadmapping chapter)
• Jeff Patton, "User Story Mapping" (slicing roadmaps)