Portfolio Planning Skill

Strategic portfolio planning for multi-project coordination and optimization.

Purpose

This skill provides a systematic approach to:

• Assess current portfolio health
• Evaluate strategic alignment
• Plan portfolio composition
• Optimize resource allocation across projects
• Balance risk across portfolio

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Prerequisites

Before starting portfolio planning, ensure:

Prerequisite	Required For	Source
Project list	Portfolio scope	Project registry
Strategic objectives	Alignment scoring	Strategy documents
Resource availability	Capacity planning	Resource planner
Budget constraints	Financial planning	Finance team

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Portfolio Planning Gates

Gate 1: Portfolio Inventory

Objective: Create complete picture of current portfolio

Actions:

1. List all active projects
2. Capture status of each project
3. Document resource allocations
4. Identify dependencies

Output: docs/pmo/{date}/portfolio-inventory.md

Checklist:

• All active projects listed
• Status captured (Green/Yellow/Red)
• Resources identified per project
• Dependencies documented

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Gate 2: Strategic Alignment Assessment

Objective: Evaluate how each project aligns with strategic objectives

Actions:

1. Map projects to strategic objectives
2. Score alignment (1-5 scale)
3. Identify orphan projects (no strategic link)
4. Flag misaligned projects

Alignment Scoring:

Score	Meaning
5	Directly enables strategic objective
4	Strongly supports strategic objective
3	Moderately supports strategy
2	Weak strategic connection
1	No clear strategic value

Output: docs/pmo/{date}/strategic-alignment.md

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Gate 3: Capacity Assessment

Objective: Understand portfolio capacity constraints

Actions:

1. Aggregate resource demand across projects
2. Compare to available capacity
3. Identify over/under allocation
4. Document skill gaps

Dispatch: resource-planner for detailed analysis

Output: docs/pmo/{date}/capacity-assessment.md

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Gate 4: Risk Portfolio View

Objective: Aggregate and correlate risks across portfolio

Actions:

1. Collect project-level risks
2. Identify correlated risks
3. Assess portfolio risk exposure
4. Plan portfolio-level mitigations

Dispatch: risk-analyst for detailed analysis

Output: docs/pmo/{date}/portfolio-risks.md

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Gate 5: Portfolio Optimization

Objective: Recommend portfolio changes for optimal value delivery

Actions:

1. Analyze portfolio balance (run/grow/transform)
2. Identify optimization opportunities
3. Recommend project prioritization
4. Propose resource reallocation

Optimization Criteria:

Criterion	Weight	Description
Strategic value	30%	Alignment with objectives
Resource efficiency	25%	Resource utilization optimization
Risk balance	20%	Portfolio risk distribution
Dependencies	15%	Dependency health
Timeline	10%	Schedule alignment

Output: docs/pmo/{date}/portfolio-recommendations.md

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Anti-Rationalization Table

See shared-patterns/anti-rationalization.md for universal anti-rationalizations.

Portfolio-Specific Anti-Rationalizations

Rationalization	Why It's WRONG	Required Action
"We know our portfolio well"	Familiarity breeds blind spots. Fresh analysis required.	Complete full inventory
"All projects are strategic"	If everything is strategic, nothing is. Differentiation required.	Score alignment objectively
"Capacity is fine, teams said so"	Self-reported capacity often optimistic. Validation required.	Verify with utilization data
"Risk aggregation is overkill"	Portfolio risk > sum of project risks. Correlation matters.	Aggregate and correlate risks

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Pressure Resistance

See shared-patterns/pressure-resistance.md for universal pressure scenarios.

Portfolio-Specific Pressures

Pressure Type	Request	Agent Response
"Just add this project, it's approved"	"Approval ≠ capacity. Portfolio impact assessment required before adding."
"Don't question the strategic projects"	"All projects require alignment verification. No exemptions for labeled 'strategic' projects."
"We don't have time for full planning"	"Incomplete planning causes downstream delays. Completing full planning cycle."

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Blocker Criteria - STOP and Report

ALWAYS pause and report blocker for:

Situation	Required Action
Portfolio capacity exceeded by >20%	STOP. Report overload. Wait for prioritization decision.
Strategic objectives unclear	STOP. Cannot score alignment. Request strategy clarification.
Resource data unavailable	STOP. Cannot assess capacity. Request resource information.
Multiple high-risk projects correlated	STOP. Report compound risk. Wait for risk mitigation decision.

Cannot Be Overridden

The following requirements are NON-NEGOTIABLE:

Requirement	Cannot Override Because
Complete portfolio inventory	Hidden projects distort capacity and priority
Strategic alignment scoring	Unscored projects cannot be prioritized
Capacity validation	Assumed capacity leads to overcommitment
Risk aggregation	Portfolio risk > sum of project risks
Stakeholder input	Decisions without stakeholder input fail adoption

If user insists on violating these:

1. Escalate to orchestrator
2. Do NOT proceed with incomplete planning
3. Document the request and your refusal

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Severity Calibration

When assessing portfolio issues:

Severity	Criteria	Examples
CRITICAL	Portfolio viability at risk	>50% projects red, capacity exceeded by >30%, strategic misalignment
HIGH	Significant portfolio impact	Multiple correlated risks, key project failing, major resource gaps
MEDIUM	Optimization needed	Imbalanced portfolio, moderate resource pressure, minor misalignment
LOW	Minor improvements possible	Process refinements, template improvements, minor optimization

Report ALL severities. Escalate CRITICAL immediately. Address HIGH this week.

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Output Format

Portfolio Status Summary

# Portfolio Status Summary - [Date]

## Portfolio Overview

| Metric | Value | Status |
|--------|-------|--------|
| Active Projects | N | - |
| Total Investment | $X | - |
| Capacity Utilization | X% | Green/Yellow/Red |
| Portfolio Risk Score | X/10 | Green/Yellow/Red |

## Strategic Alignment

| Objective | Projects | Coverage |
|-----------|----------|----------|
| [Objective 1] | [List] | X% |
| [Objective 2] | [List] | X% |

## Health Summary

| Status | Count | Projects |
|--------|-------|----------|
| Green | N | [List] |
| Yellow | N | [List] |
| Red | N | [List] |

## Recommendations

1. [Recommendation with rationale]
2. [Recommendation with rationale]

## Decisions Required

1. [Decision needed with options]
2. [Decision needed with options]

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Execution Report

Base metrics per shared-patterns/execution-report.md:

Metric	Value
Analysis Date	YYYY-MM-DD
Scope	[Portfolio name/scope]
Duration	Xh Ym
Result	COMPLETE/PARTIAL/BLOCKED

Portfolio-Specific Details

Metric	Value
projects_reviewed	N
capacity_utilization	X%
strategic_alignment_avg	X.X/5
recommendations_count	N

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When Portfolio Planning Is Not Needed

Condition	Verification
Recent planning exists (<30 days)	Reference existing portfolio plan
No new projects proposed	Verify no intake requests pending
No significant changes	Confirm no budget/resource/strategy changes
All projects on track (Green)	Verify no Yellow/Red status

MUST: Full portfolio planning REQUIRED for the following conditions:

Condition	Why Required
New project intake request	Must assess impact on portfolio
Quarterly/annual planning cycle	Regular planning cadence required
Strategic objectives changed	Alignment must be re-assessed
Resource constraints identified	Prioritization decisions needed
Multiple projects Yellow/Red	Intervention and rebalancing required

MUST: When in doubt, refresh the portfolio plan. Stale portfolio plans cause misaligned investments.