Agent skill

optionality-review

Evaluate design decisions for flexibility and reversibility

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SKILL.md

Optionality Review

Review this [CODE/ARCHITECTURE/PLAN/DECISION] through the lens of strategic optionality.

(See Quick Reference section below for optionality principles and red/green flags)

Work to Review

[PASTE YOUR WORK OR SPECIFY FILE PATH]

Context (optional)

[Any relevant context: timeline, constraints, uncertainty level]


Phase 1: Decision Classification

First, classify the key decisions using Bezos's framework:

Type 1 (One-Way Doors): Consequential and irreversible

  • Require careful, methodical consideration
  • Need broad consultation
  • Examples: Core architecture, public APIs, major vendor commitments

Type 2 (Two-Way Doors): Changeable and reversible

  • Should be made quickly with ~70% information
  • Can be changed if wrong
  • Examples: Internal tooling, feature flags, config choices

For each major decision in this work:

Decision Type Reversibility Decision Deadline Justification
[What's being decided] [1 or 2] [EASY/MODERATE/HARD/IRREVERSIBLE] [When must we decide?] [Why this classification]

Early Exit: If NO Type 1 decisions identified, output abbreviated report:

  • List Type 2 decisions with brief notes
  • Recommend: "Proceed quickly - all decisions are reversible"
  • Skip Phases 2-6

Phase 2: Alternative Paths

For Type 1 decisions, evaluate the option space (2-4 alternatives):

Current Approach

  • Description: [Brief summary]
  • Locks in: [What future choices this constrains]
  • Enables: [What this makes possible]

Alternative A

  • Description: [Different approach]
  • Would preserve: [What options stay open]
  • Trade-off: [What we'd give up]

Alternative B (if applicable)

  • Description: [Another approach]
  • Would preserve: [What options stay open]
  • Trade-off: [What we'd give up]

Alternative C, D... (add more if needed for complex decisions)

Assessment: Are alternatives adequately explored? [YES/NO] If NO, what should be investigated before committing?

For Type 2 decisions: Don't deep-dive. Briefly note 1-2 alternatives, then move on - speed matters more than exhaustive analysis for reversible decisions.


Phase 3: Exit Costs & Escape Hatches

For Type 1 decisions from Phase 1, map the exit strategy:

Decision Reversal Cost Reversal Time Escape Hatch
[Choice made] [LOW/MED/HIGH] [hours/days/weeks/months] [Concrete path to undo if needed]
[Another choice] [LOW/MED/HIGH] [hours/days/weeks/months] [How to exit]

Red Flags:

  • Irreversible decisions without clear justification
  • No escape hatches for major commitments
  • Assumptions treated as facts
  • "We can refactor later" without a concrete path

Reversibility Score: [1-10] (10 = easily reversible)


Phase 4: Failure Modes & Fallbacks

What if things go wrong?

Failure Scenario Probability Impact Fallback Plan Recovery Cost
[What could fail] [L/M/H] [L/M/H/CRITICAL] [Plan B] [time/effort]

External Dependencies:

  • Vendor lock-in: [None / Acceptable / Concerning]
  • Technology bets: [Reversible / Locked]
  • Regulatory assumptions: [Validated / Assumed]
  • Single points of failure identified: [YES/NO]

Resilience Score: [1-10] (10 = multiple fallbacks, graceful degradation)

Convergence Check: If Reversibility ≥7 AND Resilience ≥7, consider skipping to Final Report.


Phase 5: Future Value Assessment

Does this create or destroy options?

Options CREATED

  1. [New capability enabled]

    • Enables: [What becomes possible]
    • Value: [Why this matters]
  2. [Another capability]

    • Enables: [What becomes possible]
    • Value: [Why this matters]

Options DESTROYED (with justification)

  1. [Closed off possibility]
    • Prevents: [What becomes harder/impossible]
    • Justified because: [Why trade-off is acceptable]

Growth Potential

  • Can scale to 10x: [YES/PARTIALLY/NO]
  • Can add features without rewrite: [YES/PARTIALLY/NO]
  • Can be extracted/reused: [YES/PARTIALLY/NO]
  • Learning/telemetry built in: [YES/NO]

Future Value Score: [1-10] (10 = maximum option creation)


Phase 6: Decision Points & Triggers

Where should we reassess?

Milestone What to Assess Reassess Trigger Go/No-Go Criteria
[When] [What we're evaluating] [What would cause review] [How to decide]
[Next milestone] [Another assessment] [Trigger condition] [Decision criteria]
[Future checkpoint] [Long-term assessment] [Warning sign] [How to decide]

Assumption Validation:

  • Key assumptions explicitly stated
  • Validation checkpoints defined
  • Early warning metrics identified

Final Report

Scores Summary

  • Reversibility: [X/10]
  • Resilience: [X/10]
  • Future Value: [X/10]
  • Overall Optionality: [X/10] (average, or lowest score if any ≤3)

Verdict

Optionality Assessment: [FLEXIBLE | BALANCED | LOCKED_IN | CONCERNING]

  • FLEXIBLE (8-10): Excellent strategic flexibility
  • BALANCED (5-7): Acceptable trade-offs, some lock-in justified
  • LOCKED_IN (3-4): Significant constraints, ensure they're intentional
  • CONCERNING (1-2): High risk, reconsider approach

Key Findings:

  1. [Most significant optionality issue or strength]
  2. [Second finding]
  3. [Third finding]

Recommendations

Before proceeding:

  • [Critical actions to preserve flexibility]

Build in over time:

  • [Strategic improvements for future flexibility]

The Bottom Line

[2-3 sentences: Is the level of lock-in appropriate for our uncertainty level? Are we preserving the right options? What's the key trade-off?]

Human review recommended: [YES/NO] Reason: [Why human judgment needed, or why assessment is sufficient]

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