Technical Debt Register Skill

Technical Debt Register Skill

Produce a complete technical debt register for a team or service. A debt register is not a complaint list — it is a prioritized, business-impact-aware inventory that lets an engineering team make deliberate choices about which debt to pay down, in what order, and with what expected return.

Good debt management is not eliminating all debt. It is ensuring debt is visible, owned, and resolved when the interest cost exceeds the cost of fixing it.

Required Inputs

Ask for these if not already provided:

• Team or service name — what team and/or service this register covers
• Known debt items — list of known technical debt, or ask Claude to elicit them by asking about: legacy code, missing tests, outdated dependencies, architectural shortcuts, manual processes, observability gaps, security backlogs
• Tech stack — language, frameworks, infrastructure (helps Claude categorise and score items correctly)
• Team size and velocity — number of engineers and approximate story points or days per sprint (needed for effort estimates)
• Current quarter / planning period — so the roadmap targets the right timeframe

Output Format

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Technical Debt Register: [Team / Service Name]

Team: [Name] | Service(s): [Name(s)] Author: [Name] | Last updated: [Date] Planning period: [Q[X] [Year]] | Review cadence: [Monthly / Quarterly]

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Overview

[2–3 sentences describing the team's current debt situation, the main categories of debt, and the business context — e.g. are they in a growth phase where velocity matters, or approaching a compliance deadline where security debt is critical?]

Total items in register: [X] Unresolved items: [X] Critical/High priority items: [X] Estimated total resolution effort: [X story points / X engineer-weeks]

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Debt Category Definitions

Category	Description	Examples
Code quality	Code that works but is hard to change safely	Duplicated logic, deeply nested conditionals, inconsistent error handling, missing abstraction
Architecture	Structural decisions that limit scalability or increase coupling	Monolith that should be decomposed, sync calls that should be async, missing domain boundaries
Testing	Gaps in test coverage that increase regression risk	Missing unit tests, no integration tests, flaky test suite, no test data management
Security	Known vulnerabilities or missing security controls	Outdated dependencies with CVEs, missing rate limiting, hard-coded secrets, insufficient auth
Dependencies	Outdated or risky external dependencies	End-of-life libraries, major version lag, abandoned packages
Infrastructure	Infrastructure that limits reliability or developer productivity	Manual deployment steps, no IaC, single-AZ, missing autoscaling
Observability	Gaps in visibility that slow incident response	Missing metrics, no distributed tracing, poor log structure, no alerting on key SLIs
Process	Manual or error-prone operational processes	Manual DB migrations, no runbooks, tribal knowledge not documented

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Debt Register

Scoring Method

Business impact (1–5):

• 5 — Blocking growth, causing production incidents, or creating compliance risk
• 4 — Significantly slowing delivery or increasing incident likelihood
• 3 — Noticeable slowdown; manageable but accumulating
• 2 — Minor friction; low immediate risk
• 1 — Cosmetic or aspirational; no current business impact

Effort to resolve (1–5, lower = easier):

• 1 — <0.5 day; single engineer
• 2 — 0.5–2 days; single engineer
• 3 — 3–5 days; single engineer or small pair
• 4 — 1–2 weeks; team collaboration required
• 5 — >2 weeks; significant planning and coordination

Priority score = Business impact × (6 − Effort) (rewards high-impact, low-effort items)

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ID	Item	Category	Business impact (1–5)	Effort (1–5)	Priority score	Status	Owner
TD-001	[e.g. No integration tests for payment flow]	Testing	5	3	15	Open	[Name]
TD-002	[e.g. Authentication library 3 major versions behind]	Security	5	2	20	Open	[Name]
TD-003	[e.g. Database queries not using connection pooling]	Architecture	4	2	16	Open	[Name]
TD-004	[e.g. Manual deployment process for [service]]	Infrastructure	4	3	12	In progress	[Name]
TD-005	[e.g. 200-line God function in order processing]	Code quality	3	3	9	Open	[Name]
TD-006	[e.g. No structured logging — plain text only]	Observability	3	2	12	Open	[Name]
TD-007	[e.g. ORM version has known N+1 query issue]	Dependencies	3	3	9	Open	[Name]
TD-008	[e.g. No runbook for [critical operation]]	Process	3	1	15	Open	[Name]
TD-009	[e.g. Test coverage at 34% — no meaningful safety net]	Testing	4	4	8	Open	[Name]
TD-010	[e.g. Hard-coded config values in application code]	Code quality	2	1	10	Open	[Name]
TD-011	[e.g. Service deployed single-AZ with no failover]	Infrastructure	5	4	10	Open	[Name]
TD-012	[e.g. No alerting on P95 latency for [endpoint]]	Observability	4	1	20	Open	[Name]

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Category Breakdown

Category distribution (by item count):
─────────────────────────────────────────────
Code quality     ████████░░  [X items]  ([X]%)
Architecture     ██████░░░░  [X items]  ([X]%)
Testing          █████████░  [X items]  ([X]%)
Security         ████░░░░░░  [X items]  ([X]%)
Dependencies     ███░░░░░░░  [X items]  ([X]%)
Infrastructure   ████░░░░░░  [X items]  ([X]%)
Observability    ████░░░░░░  [X items]  ([X]%)
Process          ██░░░░░░░░  [X items]  ([X]%)
─────────────────────────────────────────────

Priority distribution:
Critical (score 20–25): [X items]
High     (score 12–19): [X items]
Medium   (score  6–11): [X items]
Low      (score   1–5): [X items]

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Top 5 Priority Items — Resolution Plans

TD-XXX: [Highest priority item name]

Priority score: [Score] | Category: [Category] | Owner: [Name]

Problem: [2–3 sentences describing what the debt is, how it manifests, and what pain it currently causes. Be specific — reference actual incidents, slowdowns, or risks.]

Business impact: [What happens if this is not resolved? Reference any incidents, near-misses, or growth blockers. E.g. "This caused 2 production incidents in the last quarter and adds ~30 minutes of debugging time to any change in this area."]

Resolution approach: [Clear description of the fix. Not "improve the code" — describe the actual work: "Extract the payment processing logic into a dedicated PaymentService class, write unit tests to 80% coverage, and update the 3 call sites."]

Steps:

1. [Specific, ticketable step]
2. [Specific, ticketable step]
3. [Specific, ticketable step]

Acceptance criteria:

• [Measurable criterion — e.g. "Zero hard-coded config values remain in application code"]
• [Measurable criterion — e.g. "CI pipeline passes with new tests"]
• [Measurable criterion]

Effort estimate: [X story points / X days] Suggested sprint: [Q[X] Sprint [Y] / When [dependency] is complete]

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TD-XXX: [Second priority item name]

Priority score: [Score] | Category: [Category] | Owner: [Name]

Problem: [Description]

Business impact: [Impact description]

Resolution approach: [Approach description]

Steps:

1. [Step]
2. [Step]
3. [Step]

Acceptance criteria:

• [Criterion]
• [Criterion]

Effort estimate: [X story points / X days] Suggested sprint: [Sprint or timeframe]

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TD-XXX: [Third priority item]

(Follow same format as above)

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TD-XXX: [Fourth priority item]

(Follow same format as above)

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TD-XXX: [Fifth priority item]

(Follow same format as above)

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Debt Reduction Roadmap

Guiding principles

• Allocate [X%] of each sprint's capacity to debt resolution — recommended 15–20% for healthy teams
• Security and dependency debt is addressed on a fixed cadence regardless of priority score
• No new feature work in modules with Critical debt unless the debt is scheduled for the current sprint
• Debt items closed without a resolution (accepted/deferred) must have a named owner and a review date

Quarterly plan

Quarter	Focus area	Items targeted	Estimated capacity	Expected outcome
[Q1 Year] (current)	Security + observability	TD-002, TD-012, TD-006	[X] points / [Y] eng-days	Auth library current; latency alerting live; structured logging shipped
[Q2 Year]	Architecture + reliability	TD-003, TD-011, TD-004	[X] points / [Y] eng-days	Connection pooling fixed; multi-AZ deployed; deploy automation complete
[Q3 Year]	Testing coverage	TD-001, TD-009	[X] points / [Y] eng-days	Payment flow integration tests live; overall coverage ≥60%
[Q4 Year]	Code quality + process	TD-005, TD-008, TD-010	[X] points / [Y] eng-days	God functions refactored; runbooks complete; zero hard-coded config

Sprint allocation model

Sprint capacity: [X] story points

Allocation:
  ├── Feature work:        [X * 0.75 = ~Y] points  (75%)
  ├── Debt resolution:     [X * 0.15 = ~Y] points  (15%)
  └── Unplanned/bugs:      [X * 0.10 = ~Y] points  (10%)

Debt items that fit in one sprint ([≤Y] points each):
  ✓ TD-002 ([X] points)
  ✓ TD-012 ([X] points)
  ✓ TD-006 ([X] points)
  ✓ TD-008 ([X] points)

Multi-sprint debt items (break into phases):
  ~ TD-001: Phase 1 ([X] pts) → Phase 2 ([X] pts)
  ~ TD-009: Requires dedicated debt sprint or pairing

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Accepted / Deferred Debt

Items where the cost of remediation currently exceeds the business value, accepted with explicit review dates.

ID	Item	Reason for deferral	Review date	Owner
TD-XXX	[Item]	[e.g. "Rewrite would require 3 weeks with no user-facing value at current scale; revisit at 10× traffic"]	[Date]	[Name]
TD-XXX	[Item]	[e.g. "Dependency has a CVE but no upgrade path exists until Q3; mitigated by WAF rule"]	[Date]	[Name]

Policy: No item may be deferred more than twice without escalation to the engineering manager.

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Deeper Materials

This skill ships with support files — use them when they are available:

• references/debt-pricing.md — Pricing Debt: Turning "It's Bad" Into a Number Someone Can Rank. Apply it while producing the output; it carries the calibration and judgment calls the method summary above compresses.
• templates/debt-entry.md — a fill-in version of the deliverable with the quality gates inline. Offer it when the user wants to work the document themselves rather than have it generated.

Scoring Rubric (0–40)

Score any output of this skill before handing it over; 32+ is ship-quality.

Dimension	0	5	10
Business-impact translation	Items described in engineering terms only	Impact stated but unquantified	Every item priced in business terms (risk, velocity drag, cost) a non-engineer could rank
Scoring discipline	Priorities assigned by feel	Formula used but security/dependency items still under-scored	Formula applied consistently, with the "feels technical" bias explicitly corrected
Resolution plan quality	Top items have vague intentions	Plans exist but aren't ticketable	Top-5 plans are specific, ticketable steps with sequencing and a definition of done
Capacity realism	Roadmap ignores sprint budget	Allocation stated but exceeds actual capacity	Quarterly allocation fits real capacity, and accepted/deferred items carry owners and review dates

Quality Checks

• Every item has a named owner — no unowned debt
• Priority scores are calculated using the formula, not assigned arbitrarily
• Security and dependency items are not scored below their actual business impact because they feel "technical"
• Top-5 resolution plans include specific, ticketable steps — not vague descriptions like "improve test coverage"
• The quarterly roadmap allocates realistic capacity — debt allocation does not exceed actual sprint budget
• Accepted/deferred items have a review date and a named owner — no permanently deferred items
• The register distinguishes between debt (deliberate or accumulated shortcuts) and bugs (unintended defects)
• Items are closed as resolved only when acceptance criteria are met — not when the PR is merged

Anti-Patterns

• Do not score debt items arbitrarily — priority scores must be calculated using the documented formula
• Do not conflate technical debt (deliberate shortcuts) with bugs (unintended defects) — they require different remediation strategies
• Do not underrate security and dependency items because they feel abstract — score based on actual business impact
• Do not create "permanently deferred" items — every accepted item must have a review date and named owner
• Do not include resolution plans that are vague descriptions — each plan must have specific, ticketable steps