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Software DevelopmentIntermediateUser Prompt

Technical Debt Assessor

March 28, 2026

The Technical Debt Assessor performs a structured audit of code you provide, identifying accumulated technical debt and producing a prioritized remediation plan. It categorizes debt by type (design debt, code debt, test debt, documentation debt), estimates the risk and cost of each item, and recommends a paydown sequence that balances cleanup with ongoing feature work.

Engineering leads, senior developers, and CTOs use this template during quarterly planning, before major feature additions to legacy code, or when onboarding to an inherited codebase. It is especially valuable when stakeholders need a clear, non-technical summary of why "refactoring" deserves time on the roadmap.

The prompt goes beyond listing code smells. It connects each technical debt item to concrete business risk: slower feature delivery, higher bug rates, onboarding friction, or scaling ceilings. This framing helps developers communicate the cost of inaction to product managers and executives who may not intuitively understand why a working codebase still needs investment.

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The Prompt

Assess the technical debt in the following code and produce a prioritized remediation plan:

**Project Context**:
- Application type: [e.g., B2B SaaS web app, mobile API, data pipeline]
- Tech stack: [e.g., Python/Django, React, PostgreSQL]
- Team size: [NUMBER OF DEVELOPERS working on this codebase]
- Codebase age: [e.g., 3 years, started as a prototype]
- Current pain points: [WHAT PROMPTED THIS AUDIT? e.g., "New features take 3x longer than expected", "Bugs keep appearing in the billing module"]

**Code to Assess**:
```
[PASTE THE CODE, MODULE, OR FILE(S) YOU WANT ASSESSED. For large codebases, paste the most problematic area first, or paste the directory structure and key files.]
```

**Known Constraints**:
- Upcoming priorities: [WHAT FEATURES OR DEADLINES ARE COMING THAT AFFECT REFACTORING TIMING]
- Off-limits areas: [ANYTHING YOU CANNOT CHANGE RIGHT NOW, e.g., "We cannot swap the ORM until Q3"]

Produce the assessment in this format:

1. **Executive Summary** (3-4 sentences): A non-technical overview of the codebase's health and the business risks of its current state. Written so a product manager or CTO can understand the urgency without reading the full report.

2. **Debt Inventory**: For each item of technical debt found, provide:
   - **ID**: TD-01, TD-02, etc.
   - **Category**: Design Debt (architectural issues), Code Debt (implementation smells), Test Debt (missing or inadequate tests), Dependency Debt (outdated or risky dependencies), Documentation Debt (missing or misleading docs)
   - **Description**: What the problem is and where it lives (file, module, or layer)
   - **Severity**: Critical / High / Medium / Low
   - **Business Risk**: How this debt manifests as a real-world problem (e.g., "Every new payment method requires changes in 4 files instead of 1, tripling development time and bug surface")
   - **Effort Estimate**: T-shirt size (S: hours, M: 1-3 days, L: 1-2 weeks, XL: multi-week project)
   - **Dependencies**: Other debt items that should be resolved first, or features that would be blocked

3. **Debt Distribution**: Summarize how many items fall into each category and severity level. Identify which category carries the most risk.

4. **Priority Matrix**: Rank all items by "impact over effort" ratio. The highest priority items deliver the most risk reduction for the least investment.

5. **Remediation Roadmap**: Organize the debt items into three phases:
   - **Phase 1 (Quick Wins)**: Small-effort, high-impact items to tackle immediately alongside feature work. Target: 1-2 weeks.
   - **Phase 2 (Focused Sprints)**: Medium-effort items that require dedicated sprint time. Target: 1-2 sprints.
   - **Phase 3 (Strategic Refactors)**: Large-effort items that need planning, possibly feature freezes, or phased migration. Target: quarter-level planning.
   For each phase, estimate the cumulative risk reduction (e.g., "Completing Phase 1 eliminates 40% of the identified high-severity debt").

6. **Prevention Recommendations**: 3-5 process or tooling changes that would prevent similar debt from accumulating (e.g., "Add a linting rule to enforce maximum function length", "Require test coverage for new files in CI").

Usage Tips

  • Start with the pain: Paste the module or area that causes the most frustration. Technical debt assessments are most valuable when they start with the code your team dreads touching.
  • Include the directory structure: Even if you only paste one file in detail, a tree view of the project gives the AI context about naming conventions, separation of concerns, and overall architecture.
  • Share this report with stakeholders: The Executive Summary and Business Risk fields are deliberately written in business language. Copy them directly into planning documents or sprint proposals.
  • Reassess quarterly: Run this audit every quarter on different parts of the codebase. Track how many debt items get resolved versus how many new ones appear. A growing backlog signals a systemic process problem.
  • Pair with SD-01 (Code Review Assistant): Use the Code Review Assistant for individual PRs and the Technical Debt Assessor for periodic codebase-wide audits. Together they catch debt both at the point of creation and during retrospectives.

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