Managing Tech Debt

Scope

Covers

• Identifying and making technical debt visible (including user-visible symptoms)
• Prioritizing debt work using a transparent scoring model
• Deciding refactor vs migrate vs rebuild vs deprecate with explicit criteria
• Planning incremental modernization (avoid “rewrite traps”)
• Building a business case for hard-to-measure investments (metrics + small tests)
• Creating an execution-ready paydown plan with risks, milestones, and comms

When to use

• “Create a tech debt register and prioritize what to fix next quarter.”
• “We’re considering a rewrite/migration—help us make the call and plan it safely.”
• “Our legacy system slows delivery—build a paydown plan with milestones and metrics.”
• “Leadership won’t fund refactors—quantify impact and propose a measurable plan.”

When NOT to use

• You need to respond to an active incident (use incident response/runbooks).
• You only need to fix a small localized bug or a single refactor (just do the work).
• You need a full architecture redesign from scratch without existing constraints (separate architecture/design process).
• You need roadmap prioritization across many product bets (use technical-roadmaps or prioritizing-roadmap).
• You are designing a new platform or infrastructure system, not modernizing an existing one (use platform-infrastructure).
• You need to cut scope on an active project to hit a deadline (use scoping-cutting).
• The real problem is engineering process, culture, or team dysfunction, not code (use engineering-culture).

Inputs

Minimum required

• System/service(s) in scope + brief description
• Primary pain: reliability risk, velocity tax, scalability/perf, security/compliance, operability, UX fragmentation, cost
• Time horizon (e.g., “6 weeks”, “next quarter”, “12 months”) + any fixed deadlines
• Stakeholders + decision-maker(s) (Eng/PM/Design/Leadership)
• Constraints: team capacity, freeze windows, compliance/security requirements

Missing-info strategy

• Ask up to 5 questions from references/INTAKE.md, then proceed with explicit assumptions.
• If estimates are unavailable, use ranges and label confidence.
• Do not request secrets/credentials; use redacted or synthetic identifiers if needed.

Outputs (deliverables)

Produce a Tech Debt Management Pack in Markdown (in-chat; or as files if requested):

1. Context snapshot (scope, pains, constraints, stakeholders, success definition)
2. Tech Debt Register (inventory table with owners, symptoms, impact, effort range, risks)
3. Scoring + prioritization (model + ranked list + rationale)
4. Strategy decision(s) (refactor/migrate/rebuild/deprecate) with explicit criteria
5. Execution plan (incremental milestones, sequencing, resourcing, decommission plan)
6. Migration + rollback plan (if applicable; includes “dual-run” cost/plan)
7. Metrics plan (baseline, targets, leading indicators, instrumentation gaps, small tests)
8. Risks / Open questions / Next steps (always included)

Templates: references/TEMPLATES.md

Workflow (8 steps)

1) Intake + decision framing

• Inputs: User context; references/INTAKE.md.
• Actions: Confirm the decision(s) to be made, scope boundaries, time horizon, and constraints. Define what “success” means (e.g., fewer incidents, faster deploys, simpler UX integration).
• Outputs: Context snapshot (draft).
• Checks: A stakeholder can answer: “What will we decide/do differently after reading this?”

2) Surface the “debt symptoms” (user + engineering)

• Inputs: Known pain points; incident/perf history if available; qualitative reports.
• Actions: List user-visible symptoms (inconsistent UX, broken integrations, slow workflows) and engineering symptoms (deploy pain, flaky tests, high MTTR, brittle dependencies). Map symptoms → suspected debt sources.
• Outputs: Symptoms → suspected causes map (bullet list).
• Checks: At least 1 symptom is tied to a measurable signal (latency, errors, cycle time, support volume) or explicitly marked “needs instrumentation”.

3) Build the Tech Debt Register (inventory)

• Inputs: Repos/services/components in scope; symptoms map.
• Actions: Create a debt register with a consistent schema (type, location, current workaround, impact, risk, rough effort, dependencies, owner). Separate “must fix” from “nice to have.”
• Outputs: Tech Debt Register (table).
• Checks: Every item has an owner, an impact statement, and an effort range (even if coarse).

4) Score and prioritize (make trade-offs explicit)

• Inputs: Debt register.
• Actions: Score items on impact and risk (user harm, reliability, security, velocity tax) vs effort and sequencing constraints. Produce a ranked list and explain the top 5–10.
• Outputs: Scoring model + prioritized list.
• Checks: Top-ranked items are defensible: rationale references symptoms/signals and constraints, not “taste”.

5) Decide strategy per top item: refactor vs migrate vs rebuild vs deprecate

• Inputs: Top-ranked debt items; constraints; required capabilities (incl. operational flexibility).
• Actions: For each top item, pick a strategy and document options + criteria. If proposing a rebuild, include a plan to avoid the rewrite trap: migration phases, parallel support cost, cutover and decommission.
• Outputs: Strategy decision(s) + decision memo(s).
• Checks: For any “rebuild/migrate” decision, the plan includes a decommission path and acknowledges dual-run cost.

6) Create the incremental execution plan

• Inputs: Strategy decisions; constraints; dependencies.
• Actions: Convert work into milestones (thin slices), define sequencing, and set resourcing/capacity (e.g., % per sprint). Add explicit “done means decommissioned” criteria for migrations.
• Outputs: Execution plan (milestones + owners + timeline).
• Checks: Each milestone has a measurable acceptance criterion and a rollback/stop condition.

7) Quantify value: metrics + small tests

• Inputs: Baselines (or estimates); execution plan.
• Actions: Define metrics that make the investment fundable (e.g., incident rate, MTTR, p95 latency, deploy frequency, lead time, cost). Where impact is hard to measure, propose a small test (limited rollout, canary, instrumentation spike).
• Outputs: Metrics plan (baseline → target → measurement method).
• Checks: Metrics include at least 1 leading indicator and 1 guardrail; instrumentation gaps are listed with owners.

8) Align stakeholders + quality gate + finalization

• Inputs: Draft pack.
• Actions: Add stakeholder cadence (updates, review gates). Run references/CHECKLISTS.md and score using references/RUBRIC.md. Finalize Risks / Open questions / Next steps.
• Outputs: Final Tech Debt Management Pack.
• Checks: Plan is incrementally executable, risks are explicit, and the first milestone can start immediately.

Anti-patterns (common failure modes)

1. "Big bang" rewrite — Proposing a full rewrite without migration phases, dual-run cost estimates, or decommission criteria. Result: the rewrite takes 2x longer, the old system lives on, and you maintain both indefinitely.
2. Debt register without owners — Cataloging debt items without assigning an owner or linking to user-visible symptoms. Result: the register becomes a graveyard document that nobody acts on.
3. Prioritizing by developer frustration — Ranking debt by what annoys engineers most rather than by impact on users, reliability, or velocity. Result: high-visibility-but-low-impact items consume the budget while critical reliability debt festers.
4. Metrics theater — Defining improvement metrics (deploy frequency, MTTR) without baselines or instrumentation. Result: you cannot prove the investment worked, eroding future funding for debt work.
5. Invisible paydown plan — Doing debt work silently without stakeholder communication or milestone reviews. Result: leadership sees no progress, cancels the effort, and the team loses credibility for future proposals.

Quality gate (required)

• Use references/CHECKLISTS.md and references/RUBRIC.md.
• Always include: Risks, Open questions, Next steps.

Examples

Example 1 (quarterly planning): “Use managing-tech-debt. System: payments-service. Pain: frequent incidents + slow delivery. Horizon: next quarter. Output: a Tech Debt Management Pack with a prioritized register and paydown plan.”

Example 2 (rewrite decision): “We want to rebuild our pricing engine. Compare refactor vs rebuild, include migration phases, dual-run costs, rollback plan, and a metrics-based justification.”

Boundary example (redirect — generic question): “Tell me whether tech debt is bad and how to avoid it.” Response: This skill produces an actionable management pack, not general advice. Ask for a specific system, pain point, and time horizon. Otherwise provide a minimal intake checklist and an example register schema.

Boundary example (redirect — neighbor skill): “Our roadmap has too many competing priorities and we cannot decide what to build next quarter.” Response: This is a roadmap prioritization problem, not a tech debt management task. Redirect to technical-roadmaps or prioritizing-roadmap for a prioritization framework. If tech debt items are among the competing priorities, return here to produce the debt register and paydown plan.