Purpose
Turn a raw list of portfolio assets or initiatives into a scored, ranked decision matrix that tells a portfolio manager exactly which items to accelerate, which to stop, which to watch, and which to restructure — with the reasoning and capital implications made explicit. Replaces gut-feel portfolio reviews with a repeatable, defensible scoring framework.
When to Use
Invoke this skill when the user asks to:
- Review the health of an investment portfolio, product portfolio, or initiative pipeline
- Decide which projects or bets to kill, fund, or hold
- Rank a set of assets by risk-adjusted value and strategic fit
- Reallocate budget or capital across competing initiatives
- Prepare a portfolio review for a leadership or investment committee
- Identify underperformers and hidden opportunities before a planning cycle
Inputs Required
Before starting, collect:
- Portfolio items: The list of assets, initiatives, products, or investments to screen (name + 1-line description each)
- Per-item data: Whatever is known for each — expected return/value, cost/capital committed, stage, current performance vs. plan
- Strategic goals: The 2-4 strategic priorities the portfolio is meant to serve
- Time horizon: The window over which value is measured (e.g., 12 months, 3 years)
- Resource constraint: Total budget, capital, or headcount available to allocate
- Risk tolerance: Aggressive / Balanced / Conservative
- Portfolio type: Investment / Product / Initiative-pipeline / Mixed
If per-item data is incomplete, score on available signals and flag the item as "low-confidence — needs data" rather than skipping it.
Instructions
Step 1: Establish the Scoring Model
Score each item on three dimensions, 1-5 each. Anchor the scales before scoring so ratings are consistent across the portfolio.
- Risk-Adjusted Value (1-5): Expected value discounted by probability of success and downside exposure. 5 = high upside with high confidence; 1 = low or uncertain upside relative to capital at risk. Factor in stage maturity, dependency risk, and execution risk.
- Strategic Alignment (1-5): How directly the item advances the stated strategic goals. 5 = core to a top priority; 1 = orphan bet with no clear strategic thread.
- Market Attractiveness (1-5): Size, growth, timing, and competitive position of the opportunity. 5 = growing market, strong right-to-win, good timing; 1 = shrinking or saturated space, weak position.
Weight the three dimensions per the stated risk tolerance:
- Aggressive: Value 50% / Market 30% / Alignment 20%
- Balanced: Value 40% / Alignment 35% / Market 25%
- Conservative: Alignment 45% / Value 35% / Market 20%
Step 2: Score Every Item
For each portfolio item produce:
- The three dimension scores (1-5) with a one-clause justification each
- A weighted composite score (0-5, one decimal) using the risk-tolerance weights
- A confidence flag: High / Medium / Low (Low when key data was missing or estimated)
Present as a scoring table sorted by composite score, highest first.
Step 3: Plot the Risk/Opportunity Matrix
Map each item onto a 2x2 using two axes:
- X-axis — Attractiveness: composite of Value + Market
- Y-axis — Fit: Strategic Alignment
Assign each item to a quadrant:
- Accelerate (high attractiveness, high fit): Fund aggressively; remove blockers
- Restructure (high attractiveness, low fit): Valuable but off-strategy — reposition, re-scope, or spin off
- Watch (low attractiveness, high fit): On-strategy but weak returns — set milestones and a decision date
- Stop (low attractiveness, low fit): Divest, sunset, or wind down
State the quadrant thresholds explicitly (e.g., score ≥ 3.5 = "high") so the classification is reproducible.
Step 4: Recommendation Per Item
For each item deliver one line: [STOP / ACCELERATE / WATCH / RESTRUCTURE] — [one-sentence rationale tied to its scores] — [the specific action, with a trigger or milestone where relevant].
Recommendations must be decisive. "Watch" is not a default hiding place — every Watch item gets a named milestone and a review date.
Step 5: Capital Reallocation Summary
Given the resource constraint, show the shift:
- Total resource currently committed to Stop-quadrant items (this is the freed capital)
- Where that freed capital should move (name the Accelerate items receiving it)
- The 3 highest-conviction accelerations and the 3 clearest stops
- Any concentration risk created by the reallocation (over-indexing on one theme, stage, or market)
Step 6: Portfolio-Level Read
Two to four sentences on overall portfolio health: balance across quadrants, over/under-diversification, whether the portfolio actually serves the stated strategy, and the single biggest structural risk.
Output Format
- Structure: Scoring table → matrix quadrant assignments → per-item recommendations → capital reallocation summary → portfolio-level read
- Length: 800–1,300 words depending on portfolio size
- Format: Scoring presented as a table; recommendations as a labeled list; reallocation and portfolio read as tight prose
- Sections: Scoring model note → Scoring table (sorted by composite) → 2x2 matrix quadrant breakdown → Per-item recommendations → Capital reallocation summary → Portfolio-level read
- Tone: Investment-committee direct — decisive, numbers-first, willing to recommend killing things
Quality Checklist
Before delivering output, verify:
- [ ] Every portfolio item is scored on all three dimensions — none skipped (count items in vs. out)
- [ ] Composite scores use the weights matching the stated risk tolerance
- [ ] Every item is assigned to exactly one quadrant and one Stop/Accelerate/Watch/Restructure verdict
- [ ] Every "Watch" item has a named milestone and a review date — no open-ended holds
- [ ] Capital reallocation summary balances freed capital against redeployment (the math ties out)
- [ ] Low-confidence items are flagged, not silently guessed
Notes
- The most common portfolio pathology is too many "Watch" items — force the distribution; if more than half the portfolio lands in Watch, the thresholds are too generous.
- High-attractiveness / low-fit items (Restructure) are where the sharpest value often hides — don't reflexively kill a strong asset just because it drifted off-strategy; ask whether the strategy or the asset should move.
- Freed capital from Stop items is the real output of this exercise — a screen that ends without a reallocation is just a scorecard.
- If the portfolio has fewer than 5 items, the 2x2 is still useful but note that quadrant thresholds are directional, not statistical.
How to use this skill
This file is a Claude Code skill in Anthropic's standard format — markdown with YAML frontmatter at the top.
Installing in Claude Code:
~/.claude/skills/<folder-name>/SKILL.md— auto-loads in every session anywhere on your machine (recommended for skills you'll use across multiple projects)<your-project>/.claude/skills/<folder-name>/SKILL.md— auto-loads only when working in that project (recommended for project-specific skills)
Restart Claude Code or open a new session to register.
Using in Claude.ai, ChatGPT, Gemini, or other AI tools:
- Drag this file into a new chat, or copy and paste its contents
- Send your task or request as your next message — the AI will apply the skill where it fits
For Claude Code skill details: https://docs.anthropic.com/en/docs/claude-code/skills