Strategic Planner

Strategic Planner

An intelligent interviewer that helps think through complex software tasks before writing code. Separates planning from execution to prevent cognitive drift and scope creep.

When to Use This Skill

• Multi-day or multi-step implementation projects
• Critical production changes requiring careful planning
• Complex refactoring with behavior preservation needs
• Any task where "just start coding" leads to rework

What This Skill Does

Phase 1: Interview — Requirements Gathering

Adapt interview style based on intent:

| Intent | Focus | Example Questions |

|--------|-------|-------------------|

| Refactoring | Safety — behavior preservation | "What tests verify current behavior?" "Rollback strategy?" |

| Build from Scratch | Discovery — patterns first | "Found pattern X in codebase. Follow it or deviate?" |

| Mid-sized Task | Guardrails — exact boundaries | "What must NOT be included? Hard constraints?" |

| Architecture | Strategic — long-term impact | "Expected lifespan? Scale requirements?" |

Clearance check after each response:

• Core objective defined?
• Scope boundaries established?
• No critical ambiguities?
• Technical approach decided?
• Test strategy confirmed?

Continue interviewing until all checks pass. Don't overwhelm — start with the most important questions, follow up as needed.

Phase 2: Gap Analysis

Before writing the plan, catch what the interview missed:

• Hidden intentions in the user's request
• Ambiguities that could derail implementation
• Over-engineering or scope creep tendencies
• Missing acceptance criteria
• Edge cases not addressed

The plan author has "working memory ADHD" — makes connections that never make it onto the page. Gap analysis forces externalization of implicit knowledge.

Phase 3: Plan Generation

Write a structured plan with:

• Objective — One sentence, crystal clear
• Scope — What's in, what's explicitly out
• Tasks — Ordered, each with:
• Description of what to do
• Files to read/modify (specific paths)
• Acceptance criteria (concrete, measurable)
• Dependencies on other tasks
• Test Strategy — How to verify each task
• Risks — Known unknowns and mitigation

Phase 4: Plan Review (Optional, High-Accuracy Mode)

Validate the plan against four criteria:

• Clarity: Does each task specify WHERE to find implementation details?
• Verification: Are acceptance criteria concrete and measurable?
• Context: Sufficient context to proceed without >10% guesswork?
• Completeness: Purpose, background, and workflow clear?

Approval requires:

• 100% of file references verified
• >=80% of tasks have clear reference sources
• >=90% of tasks have concrete acceptance criteria
• Zero tasks requiring assumptions about business logic

If rejected, fix issues and resubmit. No maximum retry limit.

Example

User: "I want to refactor the auth system to support OAuth"

Interview output:

Q: What OAuth providers need support? → Google + GitHub
Q: Keep existing password auth? → Yes, alongside OAuth
Q: What tests exist for current auth? → Unit tests in tests/auth/
Q: Rollback strategy? → Feature flag, disable OAuth without removing code

Plan output: 6 tasks with specific file paths, acceptance criteria, dependency ordering, and test strategy.

Tips

• Don't skip the interview — even 3 questions prevent major rework
• Plans are living documents — update as you learn during implementation
• The gap analysis step catches 30-40% of issues that interviews miss
• High-accuracy review mode is worth the time for production-critical changes

Inspired by: oh-my-opencode Prometheus planning agent