tomevault-io 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
| 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]
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.
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