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Portfolio Roadmapping Bets Methodology

Table of Contents

  1. Horizon Planning Frameworks
  2. Bet Sizing Methodologies
  3. Portfolio Balancing Techniques
  4. Dependency Mapping
  5. Exit & Scale Criteria
  6. Portfolio Review
  7. Anti-Patterns & Fixes

1. Horizon Planning Frameworks

McKinsey Three Horizons

H1: Extend & Defend Core (70%)

  • Timeline: 0-12mo | Risk: Low | Return: 10-30% | Examples: Feature improvements, optimizations

H2: Build Emerging Businesses (20%)

  • Timeline: 6-24mo | Risk: Medium | Return: 2-5x | Examples: New product lines, geographies

H3: Create Transformational Options (10%)

  • Timeline: 12-36+mo | Risk: High | Return: 10x+ | Examples: Moonshots, new business models

Adjustments: Startup (50/30/20), Enterprise (80/15/5), Scale-up (70/20/10)

Now-Next-Later

Now (Shipping this quarter): >80% confidence, clear reqs, in development Next (Starting 1-2 quarters): ~60% confidence, mostly clear, in planning Later (Future quarters): ~40% confidence, unclear, in research

Use when: Teams uncomfortable with 6-12-24mo planning

Dual-Track Agile

Discovery (Learn): User research, prototypes, experiments → Decide what to build Delivery (Ship): Build, ship, monitor, iterate

Application: H1 = delivery, H2 = mix, H3 = discovery. Discovery runs 1-2 sprints ahead.


2. Bet Sizing Methodologies

RICE Scoring

Formula: (Reach × Impact × Confidence) / Effort

  • Reach: Users affected per quarter
  • Impact: 0.25 (minimal) to 3 (massive)
  • Confidence: 50% (low) to 100% (high)
  • Effort: Person-months

Example: (5000 × 2 × 80%) / 4 = 2000 score

ICE Scoring

Formula: (Impact + Confidence + Ease) / 3 or Impact × Confidence × Ease

  • Impact: 1-10 scale
  • Confidence: 1-10 scale
  • Ease: 1-10 scale (inverse of effort)

Use when: Quick prioritization without reach data

Effort/Impact Matrix

Quadrants:

  • High Impact, Low Effort → Quick wins (do first)
  • High Impact, High Effort → Strategic (plan carefully, H2/H3)
  • Low Impact, Low Effort → Fill-ins (if spare capacity)
  • Low Impact, High Effort → Avoid

Kano Model

Basic Needs: Must-have (if missing, dissatisfied) → H1 Performance Needs: Linear satisfaction (more is better) → H1/H2 Delight Needs: Unexpected wow factors → H2/H3


3. Portfolio Balancing Techniques

70-20-10 Rule

  • 70% Core: Optimize existing (low risk, predictable return)
  • 20% Adjacent: Extend to new (medium risk, substantial return)
  • 10% Transformational: Create new (high risk, breakthrough potential)

Measure by: Bet count or effort. Red flags: >80% core (too safe), >30% transformational (too risky)

Risk-Return Diversification

Low Risk, Low Return (Core): 80-90% win rate, 1.2-1.5x return Medium Risk, Medium Return (Adjacent): 50-60% win rate, 2-3x return High Risk, High Return (Transformational): 10-30% win rate, 10x+ return

Portfolio construction: Combine to achieve desired risk/return profile

Barbell Strategy

Structure: 80-90% very safe + 10-20% very risky, 0% medium Rationale: Safe bets sustain, risky bets create upside, avoid "meh" middle

Pacing by Cycle Time

Fast (days-weeks): A/B tests, experiments → 50% Medium (months): Features, initiatives → 30% Slow (quarters-years): Platform, R&D → 20%


4. Dependency Mapping

Critical Path Method

  1. List all bets and dependencies
  2. Map dependencies (A → B → C)
  3. Calculate duration for each path
  4. Identify critical path (longest)
  5. Accelerate critical path

Example: Path A (3mo) → C (4mo) = 7mo ← Critical. Path B (2mo) → C (4mo) = 6mo (1mo slack)

Dependency Types

  • Technical: Infrastructure, APIs, data pipelines
  • Learning: Insights from experiments
  • Strategic: Prior bet must validate market
  • Resource: Team availability

Learning-Based Sequencing

Pattern: Small experiment (H1) → Validate → Large bet (H2) → Scale

Example: H1: 2-week prototype ($5K) | Exit if CTR <5% | Scale: H2: Full build ($500K) if CTR >10%


5. Exit & Scale Criteria

North Star Metric Thresholds

Example: North Star = WAU

  • Exit: If WAU lift <5% after 60 days, kill
  • Scale: If WAU lift >15%, expand to all users

Staged Funding

Stage 1 (Seed): $50K → Prototype, 100 users, 20% engagement

  • Exit if <20%, fund $200K for alpha if ≥20%

Stage 2 (Series A): $200K → Alpha, 1000 users, 10% conversion

  • Exit if <10%, fund $1M for full build if ≥10%

Kill Criteria Examples

  • Time: "If not validated in 90 days, kill"
  • Metric: "If adoption <5%, kill"
  • Cost: "If CAC >$100, kill"
  • Strategic: "If competitor launches first, reassess"

Scale Criteria Examples

  • Adoption: "If >20% adopt in 30 days, expand"
  • Engagement: "If usage >3x baseline, add features"
  • Revenue: "If ARR >$100K, hire team"
  • Efficiency: "If LTV/CAC >5, increase budget 3x"

6. Portfolio Review

Review Cadence

  • H1: Monthly (check progress, blockers, kill/pivot/scale)
  • H2: Quarterly (ready to start? dependencies? promote to H1 or push to H3?)
  • H3: Semi-annually (still strategic? market shifts? add/kill)

Kill / Pivot / Persevere / Scale

For each bet:

  • Kill: Criteria not met, no path to success
  • Pivot: Partially working, adjust approach
  • Persevere: On track, continue
  • Scale: Exceeding expectations, double-down

Portfolio Health Metrics

Velocity: Bets shipped/quarter (target: 5-10) Win Rate: % meeting scale criteria (target: 20-40%), % exited (target: 10-30%) Impact: Portfolio contribution to North Star, ROI (target: >3x) Balance: Risk 70/20/10, Horizon 50/30/20

Red flags: Win <10% (too risky), Win >80% (too conservative), Exit <5% (not killing), Exit >50% (too risky)


7. Anti-Patterns & Fixes

#1: Everything High Priority

Symptom: All must-have, no trade-offs Fix: Force-rank (only top 3 high), MoSCoW (20% must, 30% should, 30% could, 20% won't), capacity-constrain

#2: No Exit Criteria

Symptom: Bets continue indefinitely, zombie projects Fix: Set criteria upfront, review monthly, celebrate killing

#3: All Bets in H1

Symptom: Wish list, unrealistic Fix: Capacity-constrain H1, move excess to H2/H3, set expectations

#4: No H3 Pipeline

Symptom: Only H1/H2, no future exploration Fix: Reserve 10-20% for H3, run experiments, refresh quarterly

#5: All Core, No Transformational

Symptom: 100% incremental Fix: Mandate 10% transformational, innovation sprints, measure % revenue from <3yr products (target 20%+)

#6: Dependencies Ignored

Symptom: H2 depends on H1 infrastructure not prioritized Fix: Map dependencies, prioritize blockers, review critical path

#7: No Review Discipline

Symptom: Roadmap created once, never updated Fix: Monthly H1, quarterly portfolio review, version control

#8: Metrics-Free Bets

Symptom: No success metrics, unclear if worked Fix: Require metrics per bet, instrument before ship, review post-launch

#9: Over-Optimistic Impact

Symptom: Every bet "10x potential" Fix: Use baselines, benchmark, risk-adjust (assume 50% success)

#10: No Portfolio Balance

Symptom: All small (busy work) or all large (nothing ships) Fix: Mix sizes (50% S, 30% M, 15% L, 5% XL), cycles (fast/medium/slow), risk (70/20/10)


Quick Reference

When to Use Each Framework

Horizon Planning: McKinsey (classic), Now-Next-Later (adaptive), Dual-Track (continuous) Bet Sizing: RICE (quantitative), ICE (quick), Effort/Impact (visual), Kano (user satisfaction) Balancing: 70-20-10 (risk), Risk-Return (diversification), Barbell (extremes), Pacing (cycles) Sequencing: CPM (critical path), Dependency Matrix (complex), Learning-Based (de-risk) Criteria: North Star (aligned), Staged Funding (VC model), Time/Metric/Cost/Strategic (varied) Review: Monthly/Quarterly/Semi-annual (by horizon), Kill/Pivot/Persevere/Scale (framework)

Common Patterns

Product: H1: Quick wins + strategic features | H2: Major features + platform | H3: Exploratory | 60% incremental, 30% substantial, 10% breakthrough

Tech: H1: Stability + migration start | H2: Complete migration + improvements | H3: Next-gen research | 50% maintain, 30% improve, 20% transform

Innovation: H1: Scale validated + new tests | H2: Strategic bets + experiments | H3: Moonshots | 70% core, 20% adjacent, 10% transformational

Marketing: H1: Optimize proven + test new | H2: Scale winners + brand | H3: Positioning + market entry | 70% performance, 20% growth, 10% brand

Success Criteria

✓ Strategic theme clear & measurable ✓ Bets sized (S/M/L/XL) & impact quantified (1x/3x/10x) ✓ Sequenced across H1/H2/H3 with dependencies mapped ✓ Exit & scale criteria defined per bet ✓ Portfolio balanced (risk, horizon, size) ✓ Capacity feasible (effort ≤ capacity × 0.8) ✓ Impact ladders to theme (risk-adjusted) ✓ Review cadence established

Red Flags

No theme → wish list All "Large" → no prioritization No exit criteria → zombies Imbalanced (all core or all moonshots) Dependencies ignored → blocking Overcommitted (>80% capacity) Impact below goal No review → stale roadmap