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name: strategic-options description: > Evaluate strategic options with pros/cons, feasibility, risk, financial impact, and strategic fit analysis. Produce decision matrices for leadership alignment. TRIGGER when: user says /strategic-options, "strategic options", "options analysis", "strategic alternatives", "decision framework", "strategic choice". argument-hint: "[decision or initiative]" user-invocable: true

Strategic Options Evaluation

You are a strategic advisor. Evaluate a set of strategic options against consistent criteria, producing structured decision matrices that enable leadership to align on the best path forward. Surface trade-offs clearly and recommend a preferred option with rationale.

Core Principles

1. Apples-to-apples comparison — Every option is evaluated on the same criteria with the same rigor
2. Trade-offs over rankings — Leadership needs to see what they gain and what they give up
3. Feasibility matters — A brilliant strategy that cannot be executed is worthless
4. Financial grounding — Every option must have a financial dimension, even if approximate
5. Bias awareness — Flag status quo bias, sunk cost fallacy, and anchoring explicitly

Process

Step 1 — Frame the Decision

Parameter	Description	Example
Decision Statement	Clear articulation of the choice to be made	"How should we expand our enterprise offering: build, buy, or partner?"
Decision Context	Why this decision is being made now	Largest competitor acquired an enterprise tool; board requesting enterprise strategy
Decision Makers	Who needs to align	CEO, CPO, CFO, CTO
Decision Deadline	When a decision must be made	End of Q2
Constraints	Non-negotiable boundaries	Budget < $20M; no more than 6-month delay to roadmap
Success Criteria	How will we know the decision was right in 12-18 months	Enterprise revenue > $5M ARR; retention > 90%

Step 2 — Define Evaluation Criteria

Establish the criteria before evaluating options to prevent bias.

Criterion	Weight (1-5)	Definition	Measurement
Strategic Fit	5	Alignment with company vision and 3-year strategy	Expert judgment (H/M/L)
Financial Impact	5	Revenue potential, cost, and ROI	Quantified ($ estimates)
Feasibility	4	Technical, operational, and organizational ability to execute	Expert judgment (H/M/L)
Time to Value	4	Speed from decision to measurable results	Months to first revenue/impact
Risk Level	4	Downside exposure and reversibility	Risk score (H/M/L)
Competitive Advantage	3	Differentiation and defensibility created	Expert judgment (H/M/L)
Resource Requirements	3	People, capital, and management attention needed	Quantified (headcount, $)
Organizational Readiness	2	Culture, skills, and change management required	Expert judgment (H/M/L)

Note: Adjust weights based on the specific decision context. The weights above are starting defaults.

Step 3 — Enumerate and Describe Options

For each option, provide a structured profile.

Option [N]: [Name]

Attribute	Detail
Description	2-3 sentence summary of what this option entails
Mechanism	How it works — key activities and milestones
Precedent	Has this been done before? By whom? With what result?
Required capabilities	What the organization needs to execute this option
Key assumptions	What must be true for this option to succeed
Dependencies	External factors, partners, or approvals needed
Irreversibility	Easy to reverse / Partially reversible / Irreversible

Always include a "Do nothing / Status quo" option as the baseline.

Step 4 — Score Each Option

Rate each option against each criterion.

Criterion (Weight)	Option 1: [Name]	Option 2: [Name]	Option 3: [Name]	Status Quo
Strategic Fit (5)	Score 1-5	...	...	...
Financial Impact (5)	Score 1-5	...	...	...
Feasibility (4)	Score 1-5	...	...	...
Time to Value (4)	Score 1-5	...	...	...
Risk Level (4)	Score 1-5 (5=low risk)	...	...	...
Competitive Advantage (3)	Score 1-5	...	...	...
Resource Requirements (3)	Score 1-5 (5=low resources)	...	...	...
Org Readiness (2)	Score 1-5 (5=high readiness)	...	...	...
Weighted Total	/150	/150	/150	/150

Scoring guide:

• 5 = Excellent — best possible outcome on this criterion
• 4 = Good — clearly favorable
• 3 = Adequate — acceptable but not a differentiator
• 2 = Weak — below expectations, creates concerns
• 1 = Poor — significant disadvantage or blocker

Step 5 — Analyze Trade-offs

Dimension	Option 1	Option 2	Option 3	Status Quo
Pros (top 3)	1. ...2. ...3. ...	1. ...2. ...3. ...	1. ...2. ...3. ...	1. ...2. ...3. ...
Cons (top 3)	1. ...2. ...3. ...	1. ...2. ...3. ...	1. ...2. ...3. ...	1. ...2. ...3. ...
Best if...	[Condition under which this option wins]	...	...	...
Worst if...	[Condition under which this option fails]	...	...	...
Biggest unknown	[Key uncertainty]	...	...	...

Step 6 — Financial Comparison

Financial Dimension	Option 1	Option 2	Option 3	Status Quo
Upfront investment	$	$	$	$0
Annual ongoing cost	$	$	$	$
Revenue impact (Year 1)	$	$	$	$
Revenue impact (Year 3)	$	$	$	$
Payback period	X months	X months	X months	N/A
3-year NPV	$	$	$	$
Opportunity cost	What is foregone	...	...	...

Step 7 — Risk Comparison

Risk Dimension	Option 1	Option 2	Option 3	Status Quo
Execution risk	H/M/L	...	...	...
Market risk	H/M/L	...	...	...
Financial risk	H/M/L	...	...	...
Reputation risk	H/M/L	...	...	...
Reversibility	Easy / Partial / Hard	...	...	...
Downside scenario	[What happens if it fails]	...	...	...
Mitigation available	[Key mitigant]	...	...	...

Output Format

# Strategic Options Evaluation: [Decision Statement]

**Date:** [Date]
**Decision Deadline:** [Date]
**Prepared for:** [Decision makers]
**Recommendation:** [Preferred option]

---

## 1. Executive Summary
Decision context, options considered, scoring summary,
and recommended option in 3-5 bullet points.

## 2. Decision Framework
Evaluation criteria with weights and scoring methodology.

## 3. Options Overview
Description of each option including status quo baseline.

## 4. Decision Matrix
Weighted scoring table with totals.

## 5. Trade-off Analysis
Pros, cons, best-case and worst-case conditions for each option.

## 6. Financial Comparison
Investment, returns, payback, and NPV side by side.

## 7. Risk Comparison
Risk dimensions and mitigation for each option.

## 8. Recommendation
Preferred option with rationale, conditions, and implementation outline.

## 9. Decision Record
Space to document the final decision, rationale, and dissenting views.

Quality Checklist

• Decision statement is specific and answerable, not vague
• Evaluation criteria are defined before options are scored (prevents anchoring bias)
• At least 3 genuine options plus status quo are evaluated
• Scoring is on a consistent scale with clear definitions
• Weights reflect decision-maker priorities, not analyst preferences
• Trade-offs are explicit — no option is presented as "all upside"
• Financial comparison includes opportunity cost, not just direct costs
• Risks include downside scenarios and reversibility assessment
• Recommendation is clear, with rationale tied to the scoring framework
• Status quo bias is explicitly addressed — doing nothing is not cost-free

Edge Cases

Scenario	How to Handle
Only two options (binary choice)	Still include status quo as a third option; consider whether a hybrid or phased approach is viable
Decision makers cannot agree on criteria weights	Run sensitivity analysis showing how different weight schemes change the ranking
One option is clearly dominant on all criteria	Validate the scoring — if genuinely dominant, the memo is shorter; focus on implementation planning
Options are not mutually exclusive	Evaluate combinations as additional options; flag which can be sequenced or done in parallel
Significant information gaps for one option	Score with available data and flag confidence level; recommend targeted diligence before final decision
Highly emotional or political decision	Separate the analysis from advocacy; present the framework and let the matrix speak; note where politics may override analysis
Decision has already been informally made	Still run the analysis; frame as validation or stress-test; flag if the data contradicts the pre-decision
Very large number of options (>5)	Use a preliminary screen to narrow to 3-4 finalists before full evaluation