Purpose
Turn a messy list of competing priorities, requests, and constraints into a structured decision brief — a small set of coherent roadmap options, each with honest pros and cons, that leadership can actually choose between. Eliminates the "everything is P0" stalemate and gives the room a clear decision to make instead of a debate to have.
When to Use
Invoke this skill when the user asks to:
- Prepare a roadmap or prioritization review for leadership
- Frame competing feature requests or initiatives as decision options
- Resolve a conflict where multiple teams want the same capacity
- Package tradeoffs for an executive or steering committee decision
- Turn a backlog of "must-haves" into a realistic sequenced plan
- Present quarterly planning options with clear pros and cons
Inputs Required
Before starting, collect:
- Competing priorities: The list of initiatives, features, or bets under consideration (5+ items ideal)
- Capacity constraint: Available capacity — team size, sprint count, quarter length, or budget
- Strategic goals: The 1-3 company or product objectives this planning cycle serves
- Key stakeholders: Which teams or leaders are advocating for what, and any known tension
- Hard commitments: Anything already promised — contractual, legal, or dependency-locked
- Decision deadline: When the choice must be made and by whom
- Known unknowns: Estimates that are shaky, dependencies not yet confirmed, or research still open
If effort estimates are missing, use relative T-shirt sizing (S/M/L/XL) and flag the assumption.
Instructions
Step 1: Normalize and Cluster the Priorities
Before framing options, clean the input:
- Restate each priority in one outcome-oriented line (what the user gets, not the feature name)
- Tag each with: strategic goal it serves, rough effort (S/M/L/XL), and confidence in that estimate (High/Med/Low)
- Cluster items that are dependent, complementary, or mutually exclusive — these travel together across options
- Flag any item that is a hard commitment (non-negotiable) versus a discretionary bet
Step 2: Establish the Capacity Envelope
Define the constraint that forces the tradeoff:
- State total available capacity in a concrete unit (engineer-weeks, sprint-slots, or % of quarter)
- Subtract hard commitments and typical overhead (support, tech debt, bugs — reserve 15-25% if not specified)
- The remaining capacity is the "discretionary budget" that every option must fit inside
- If nothing fits, that itself is the headline — say so plainly
Step 3: Construct 3-5 Coherent Options
Each option is a different strategy, not a random subset. Build options along a spectrum:
- The Focus Option: Go deep on one strategic bet; defer everything else
- The Balanced Option: A mix across goals — some progress everywhere, deep progress nowhere
- The Fast-Wins Option: Maximize shipped items and momentum; favor small, high-confidence work
- The Foundation Option: Invest in enablers (platform, tech debt, infra) that unlock future speed
- The Commitment-First Option (include only if hard commitments dominate capacity): Honor obligations, minimal discretionary work
Choose the 3-5 that are genuinely viable given the inputs. Do not invent options that don't fit capacity.
For each option, produce:
- Name and one-line thesis: What this option bets on
- What's in: The specific priorities included (from Step 1)
- What's deferred: The specific priorities cut — name them, don't hide them
- Effort fit: Confirm it fits the discretionary budget from Step 2
- Pros: 2-4 concrete advantages tied to the strategic goals
- Cons: 2-4 honest costs, risks, or stakeholders who lose
- Risk profile: Low / Medium / High, with the single biggest risk named
- Who's happy / who's not: Map to the stakeholders from inputs
Step 4: Surface the Real Tradeoff Axis
Name the underlying tension the options reveal — usually one of:
- Depth vs. breadth
- Short-term momentum vs. long-term leverage
- Certainty vs. upside
- Commitment safety vs. strategic ambition
State it in one sentence so leadership sees they're deciding a philosophy, not just a list.
Step 5: Recommend and Frame the Decision
- Make one recommendation with a 2-3 sentence rationale tied to the stated strategic goals
- State the single question leadership must answer to unblock the choice (e.g., "Are we optimizing for the enterprise renewal or for new-segment growth this quarter?")
- List any assumption that, if wrong, would change the recommendation
Output Format
- Structure: Executive summary → normalized priority table → option comparison (one structured block per option) → tradeoff axis → recommendation
- Length: 800–1,200 words
- Format: Structured document with a comparison table for options at-a-glance, then detailed blocks
- Sections: Summary → Priorities & Capacity → Options (3-5) → Comparison Table → The Core Tradeoff → Recommendation & Decision Question
- Tone: Product leader in a planning review — decisive, honest about costs, no false balance; makes a call rather than hedging
Quality Checklist
Before delivering output, verify:
- [ ] Every option fits within the stated discretionary capacity — no option quietly over-allocates
- [ ] Each option explicitly names what is deferred, not just what's included
- [ ] Every option has both pros AND cons (no all-upside option)
- [ ] Hard commitments appear in every viable option unless the option is explicitly flagged as ignoring them
- [ ] The core tradeoff axis is stated in one plain sentence
- [ ] A single recommendation and a single decision question are provided — no ending on "it depends"
Notes
- The most common failure in roadmap reviews is presenting a list instead of a decision — the value here is forcing 3-5 mutually exclusive strategies, not ranking a backlog
- If two options end up nearly identical, collapse them — leadership can't choose between near-duplicates
- When effort estimates are low-confidence, say so in the option's risk profile rather than laundering uncertainty into false precision
- The recommendation should be defensible even to the stakeholders it disadvantages — name their loss openly and it lands better than pretending everyone wins
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