portfolio-roadmapping-bets

# Portfolio Roadmapping Bets

## Table of Contents
1. [Purpose](#purpose)
2. [When to Use](#when-to-use)
3. [What Is It?](#what-is-it)
4. [Workflow](#workflow)
5. [Common Patterns](#common-patterns)
6. [Guardrails](#guardrails)
7. [Quick Reference](#quick-reference)

## Purpose

Create strategic portfolio roadmaps that balance exploration vs exploitation, size bets by effort and impact, sequence initiatives across time horizons, and set clear exit/scale criteria for disciplined resource allocation.

## When to Use

**Use this skill when:**

### Portfolio Context
- Managing 5+ initiatives requiring sequencing and trade-offs
- Balancing quick wins vs strategic bets vs R&D exploration
- Allocating scarce resources (budget, people, time) across competing priorities
- Planning across multiple time horizons (H1: 0-6mo, H2: 6-12mo, H3: 12-24mo+)

### Decision Complexity
- Initiatives have dependencies requiring careful sequencing
- Exit criteria needed to kill or scale experiments
- Risk/return profiles vary widely (low-risk incremental vs high-risk transformational)
- Portfolio balance matters (70% core, 20% adjacent, 10% transformational)

### Stakeholder Communication
- Executives need portfolio-level view of roadmap with strategic rationale
- Teams need clarity on what's now vs next vs later
- Investors or board want visibility into innovation pipeline and resource allocation

**Do NOT use when:**
- Single initiative with clear priority (use one-pager-prd or project-risk-register instead)
- Purely operational prioritization without strategic horizons (use prioritization-effort-impact)
- No resource constraints or trade-offs (just do everything)

## What Is It?

**Portfolio Roadmapping Bets** is a framework for managing a portfolio of initiatives across time horizons using betting language to:
- **Size bets**: Estimate effort (S/M/L) and impact (1x/3x/10x potential)
- **Sequence bets**: Order initiatives based on dependencies, learning, and strategic timing
- **Set bet