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

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

Portfolio Planning Gates

Gate 1: Portfolio Inventory

Objective: Create complete picture of current portfolio

Actions:

• List all active projects

• Capture status of each project

• Document resource allocations

• 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

Gate 2: Strategic Alignment Assessment

Objective: Evaluate how each project aligns with strategic objectives

Actions:

• Map projects to strategic objectives

• Score alignment (1-5 scale)

• Identify orphan projects (no strategic link)

• 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

Gate 3: Capacity Assessment

Objective: Understand portfolio capacity constraints

Actions:

• Aggregate resource demand across projects

• Compare to available capacity

• Identify over/under allocation

• Document skill gaps

Dispatch: resource-planner for detailed analysis

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

Gate 4: Risk Portfolio View

Objective: Aggregate and correlate risks across portfolio

Actions:

• Collect project-level risks

• Identify correlated risks

• Assess portfolio risk exposure

• Plan portfolio-level mitigations

Dispatch: risk-analyst for detailed analysis

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

Gate 5: Portfolio Optimization

Objective: Recommend portfolio changes for optimal value delivery

Actions:

• Analyze portfolio balance (run/grow/transform)

• Identify optimization opportunities

• Recommend project prioritization

• 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

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

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."

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:

• Escalate to orchestrator

• Do NOT proceed with incomplete planning

• Document the request and your refusal

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.

Output Format

Portfolio Status Summary

Portfolio Status Summary - [Date]

Portfolio Overview

Strategic Alignment

Health Summary

Recommendations

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

Decisions Required

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

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

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.