Product Roadmapping and Portfolio Management

Build roadmaps that communicate strategic intent without pretending to predict the future. This skill covers outcome-based sequencing, strategic-bet management, and portfolio-level choices — not feature-level prioritization or project scheduling.

Core Principles

1. Roadmaps are not project schedules. A roadmap communicates strategic direction and sequencing intent. It does not commit to dates by default. The default view is Now/Next/Later; dates appear only when explicitly labeled as commitments.

2. Distinguish four categories in every artifact. Every roadmap output separates evidence (observed data), assumptions (beliefs not yet validated), commitments (decisions with consequences for reversal), and options (alternatives under consideration).

3. Bets, not plans. Each roadmap item is a strategic bet — an investment with an expected outcome, a confidence level, explicit dependencies, and pre-defined continue/pause/kill/revisit criteria. A roadmap is a portfolio of bets, not a to-do list.

4. Portfolio thinking scales up and down. The same bet-record and roadmap structure works for a single product and for a portfolio of products.

Loading Guide

File	Load when
references/outcome-roadmapping.md	Building or reviewing a Now/Next/Later outcome roadmap
references/strategic-bets.md	Defining, evaluating, or comparing strategic bets
references/dependency-confidence-view.md	Mapping cross-bet dependencies or calibrating confidence
references/scenario-comparison.md	Comparing alternative futures or building scenario plans
references/roadmap-review-cadence.md	Designing or running a roadmap review process
references/discovery-brief.md	Understanding ownership boundaries and routing rules
templates/outcome-roadmap.md	Fillable Now/Next/Later roadmap template
templates/bet-record.md	Fillable strategic-bet record
templates/roadmap-review-record.md	Recording a roadmap review session

Working Method

1. Start with outcomes, not features

Define outcomes as measurable "from → to" statements. Route evidence to product-analytics-and-measurement.

2. Map the Now/Next/Later landscape

Now = committed (WIP-limited), Next = validated/provisional, Later = options only. Dates only when labeled as commitments.

3. Build bet records

Every bet: outcome hypothesis, evidence, confidence (H/M/L with rationale), risk, dependencies, capacity, continue/pause/kill/revisit criteria.

4. Map dependencies and confidence

Blocking, enabling, shared-capacity, external dependencies. Effective confidence bounded by dependency health.

5. Compare scenarios

Base case + alternative scenarios for consequential decisions. Identify robust, conditional, fragile bets.

6. Define review cadence

Monthly for Now, quarterly for Next/Later. Record decisions with rationale.

7. Communicate to stakeholders

Executive narrative, team view, external/customer view — each tailored.

Routing Table

When the task involves...	Route to...
RICE scoring, MoSCoW prioritization, OST workflow	product-methodology — canonical tactical owner
Kano model, OST strategic framing, competitive positioning	product-strategy — strategic frameworks
Capital allocation, M&A portfolio choices	strategy-frameworks — corporate strategy
Delivery flow, WIP limits, throughput, cycle time	kanban-guru — execution-level flow
Evidence, metrics, analytics instrumentation	product-analytics-and-measurement — analytics layer (prose reference)
Implementation planning for approved bets	implementation-planning — handoff target (prose reference)
Experiment design for low-confidence bets	product-experimentation — downstream consumer (prose reference)
Adoption measurement for shipped bets	product-adoption — downstream consumer (prose reference)
Lifecycle learning from bet outcomes	product-lifecycle-learning — downstream consumer (prose reference)

When Not to Use

• For tactical prioritization mechanics (RICE scores, MoSCoW buckets, Kano categorization, OST trees): route to product-methodology or product-strategy. This skill references these frameworks only to describe where they fit, never to re-explain formulas or mechanics.
• For cross-project program coordination (integrated dependencies, shared capacity, program benefits, or transformation delivery): route to technical-program-management. This skill sequences product bets; it does not coordinate their technical program execution.
• For project scheduling, Gantt charts, or milestone tracking: route to technical-project-management for ongoing project control; use implementation-planning for detailed planning of approved work. This skill owns outcome roadmaps.
• For delivery-flow management: route to kanban-guru.
• For corporate capital allocation and M&A portfolio decisions: route to strategy-frameworks.
• For shaping a single bet (setting its appetite, narrowing it into a bounded problem, writing its pitch): route to product-shaping. This skill sequences bets across cycles at the portfolio level; shaping packages one bet before it enters a roadmap — "strategic bet" here means a roadmap entry with sequencing criteria, not the shaped single-project commitment that product-shaping produces.

Evidence, Assumptions, Commitments, and Options

Every roadmap artifact distinguishes these four categories:

Category	Definition	Example
Evidence	Observed data, validated learning, experiment results	"A/B test showed 12% lift in retention (p < 0.05, n=4,200)"
Assumptions	Beliefs not yet validated	"We assume users grant notification permissions at ~40%"
Commitments	Decisions with defined consequences for reversal	"Q3: 8 engineer-weeks for payments migration"
Options	Alternatives under consideration	"Build in-house vs. integrate third-party"

An artifact that mixes assumptions into evidence or presents options as commitments is not a valid output of this skill.