Overview
Technical debt refers to the implied cost of additional rework caused by choosing expedient solutions now instead of better approaches that would take longer. It accumulates through shortcuts, outdated dependencies, poor documentation, and evolving requirements that leave code misaligned with current needs.
Hiring specifically for technical debt reduction requires finding engineers who genuinely enjoy maintenance and improvement work—not everyone does. These engineers bring experience with legacy systems, knowledge of refactoring patterns, and strategies for incremental improvement that don't require risky big-bang rewrites.
The ideal candidate for debt work is a systematic thinker who appreciates clean code and finds satisfaction in improvement rather than novelty. They've inherited messy codebases before, improved them without breaking everything, and can articulate why this work matters to non-technical stakeholders. This isn't about finding someone willing to do "the boring work"—it's about finding someone for whom this IS the interesting work.
What Success Looks Like
Before you start hiring, define what success means for your debt reduction initiative. Vague goals like "improve code quality" lead to unfocused efforts and frustrated engineers. Be specific about outcomes.
Measurable Success Indicators
Velocity and Delivery
- Feature development time decreases (measured by cycle time)
- Sprint commitments are met more consistently
- Engineers estimate more accurately (reduced variance)
- New features require less "hidden work" to implement
Quality and Stability
- Bug rates in legacy areas decrease month-over-month
- Production incidents related to legacy systems decline
- Mean time to recovery (MTTR) improves
- Regression rates drop after deployments
Developer Experience
- Developer satisfaction surveys improve
- Engineers stop avoiding certain parts of the codebase
- Onboarding time for new hires decreases
- Code review turnaround time improves (cleaner code is easier to review)
Technical Health
- Test coverage in critical paths increases
- Build times decrease
- Deployment frequency can increase safely
- Security vulnerabilities in dependencies are patched
Red Flags That Debt Work Isn't Working
Watch for these warning signs:
- Engineers are "refactoring" but nothing measurably improves
- Debt work keeps getting interrupted for "urgent" features
- The team is rewriting rather than incrementally improving
- Stakeholders have lost visibility into progress
- Engineers working on debt are becoming isolated from product teams
- New debt is accumulating faster than old debt is paid down
Types of Technical Debt (and Who Addresses Each)
Not all technical debt is the same, and different types require different skills to address. Understanding what you're dealing with helps you hire the right people.
Code Quality Debt
What it looks like: Messy code, duplicate logic, unclear naming, missing tests, complex conditionals, long methods, tight coupling.
Who fixes it: Any experienced engineer with refactoring skills. This is the most common type and doesn't require specialized expertise—just patience, good judgment, and testing discipline.
Skills needed: Refactoring patterns, test-writing ability, code review experience, systematic approach to incremental change.
Architecture Debt
What it looks like: Monolithic systems that should be decomposed, outdated patterns (e.g., MVC when event-driven would be better), synchronous operations that should be async, missing abstraction layers.
Who fixes it: Senior engineers with system design experience. Architecture changes require understanding the full system, managing complex migrations, and making decisions that affect the codebase for years.
Skills needed: System design, distributed systems knowledge, migration planning, strangler fig pattern implementation, backward compatibility management.
Dependency Debt
What it looks like: Outdated libraries with security vulnerabilities, deprecated frameworks, unsupported language versions, packages that haven't been updated in years.
Who fixes it: Engineers with good DevOps instincts and testing discipline. Dependency updates seem simple but often cascade into breaking changes that require careful handling.
Skills needed: Dependency management tooling, semantic versioning understanding, integration testing, rollback strategies, security vulnerability assessment.
Infrastructure Debt
What it looks like: Manual deployment processes, missing CI/CD, inadequate monitoring, no infrastructure-as-code, manual scaling, undocumented server configurations.
Who fixes it: Platform engineers or DevOps-minded developers. This debt requires different skills than application code—infrastructure thinking, automation mindset, and operational experience.
Skills needed: CI/CD pipeline design, infrastructure-as-code (Terraform, Pulumi), monitoring and observability, containerization, automation scripting.
Knowledge Debt
What it looks like: No documentation, tribal knowledge held by one person, unclear system boundaries, missing runbooks, no architecture decision records.
Who fixes it: Engineers who value documentation and knowledge sharing. This is often overlooked but critical—technical debt in people's heads is the hardest to pay down.
Skills needed: Technical writing, diagramming, knowledge management, communication, patience for interviewing system experts.
The Ideal Candidate Profile
Core Attributes for Technical Debt Work
| Attribute | Why It Matters | How to Assess |
|---|---|---|
| Legacy system experience | Has navigated old codebases without drowning | Ask about specific legacy projects |
| Incremental mindset | Won't propose risky big-bang rewrites | Discuss approach to large changes |
| Testing discipline | Can add tests to untested code safely | Ask about testing legacy code |
| Patience and persistence | Debt work is slow; quick wins are rare | Check references on long projects |
| Communication skills | Must justify debt work to stakeholders | Have them explain technical concepts |
| Business awareness | Prioritizes debt that matters to the business | Ask about ROI decisions |
Experience Level: Senior Required
Technical debt work is not for junior engineers. Here's why:
What juniors lack:
- Pattern recognition for what "good" looks like
- Judgment about which debt matters
- Experience with large-scale refactoring
- Political capital to advocate for debt work
- Ability to mentor others on improvement practices
The right experience level:
- 5-8 years minimum for individual contributor debt work
- 8+ years for leading a debt reduction initiative
- Mix of greenfield and brownfield experience (both perspectives are valuable)
- Ideally: has inherited a messy codebase and improved it without breaking it
Personality Fit: Who Actually Enjoys This Work
Not every engineer finds debt work satisfying. The best candidates:
- Get genuine satisfaction from making things better (not just making new things)
- Enjoy detective work and understanding why systems evolved the way they did
- Are patient with slow, incremental progress
- Find clean code aesthetically pleasing
- Are comfortable with ambiguity and incomplete information
- Don't need the dopamine hit of shipping new features constantly
Red flag candidates:
- Only want to work on new features
- Have never maintained a system they didn't build
- Prefer "burn it down and start over" to incremental improvement
- Get frustrated when work doesn't show immediate results
- Dismiss existing code without understanding its context
Positioning the Role (Not "Maintenance Work")
Why Positioning Matters
How you describe this role determines who applies. Call it "maintenance work" and you'll attract people who couldn't get a better offer. Position it correctly and you'll attract engineers who genuinely excel at this work.
Framing That Attracts Strong Candidates
Instead of: "Fix legacy code"
Say: "Modernize critical systems that power our business"
Instead of: "Maintenance engineer"
Say: "Platform Quality Engineer" or "Systems Improvement Lead"
Instead of: "Clean up technical debt"
Say: "Lead strategic technical investments to accelerate engineering velocity"
Instead of: "Work on old code"
Say: "Transform a mature codebase while maintaining reliability for millions of users"
What Strong Candidates Want to Hear
- Authority to make changes — Not just identifying problems, but actually fixing them
- Executive support — Leadership understands and backs this investment
- Measurable impact — Clear metrics to show their work matters
- Reasonable timeline — Not a death march with unrealistic deadlines
- Team integration — Not isolated from the engineers building features
- Technical challenge — The problems are genuinely interesting, not just tedious
What to Be Honest About
Don't oversell. Engineers can smell inauthenticity. Be upfront about:
- The actual state of the codebase (they'll see it anyway)
- How much organizational support exists for debt work
- The timeline and resources allocated
- Whether debt work has been attempted before (and what happened)
- The balance between debt work and feature pressure
Interview Focus: Assessing Refactoring Experience
Key Interview Questions
Question 1: "Tell me about a legacy system you inherited. How did you approach improving it?"
| Good Signs | Red Flags |
|---|---|
| Describes systematic discovery phase | Jumped straight to rewriting |
| Mentions adding tests before changing | Refactored without tests |
| Used incremental approach | Proposed big-bang replacement |
| Considered business priorities | Purely technical focus |
| Can describe measurable outcomes | Vague about results |
Question 2: "How do you prioritize which technical debt to address first?"
| Good Signs | Red Flags |
|---|---|
| Considers business impact and risk | Personal preference only |
| Mentions security/stability concerns | No structured framework |
| Talks about team pain points | Ignores developer experience |
| Balances effort vs. value | Wants to fix everything |
| Involves stakeholders in decisions | Makes decisions in isolation |
Question 3: "Describe a time you had to add tests to code that wasn't written with testing in mind."
| Good Signs | Red Flags |
|---|---|
| Mentions characterization tests | Rewrote the code to test it |
| Discusses seams and dependency injection | Gave up when it was hard |
| Focuses on high-risk areas first | Insisted on 100% coverage |
| Pragmatic about effort vs. value | Dogmatic about testing rules |
Question 4: "How do you get buy-in for technical debt work from non-technical stakeholders?"
| Good Signs | Red Flags |
|---|---|
| Translates to business impact | Uses only technical jargon |
| Provides concrete examples and metrics | Can't explain why it matters |
| Proposes small wins to build trust | Demands large upfront investment |
| Shows ROI thinking | Expects automatic support |
Question 5: "Tell me about a refactoring that went wrong. What happened and what did you learn?"
| Good Signs | Red Flags |
|---|---|
| Takes ownership of mistakes | Blames others or circumstances |
| Describes specific learnings | Vague or defensive answers |
| Changed approach afterward | Same mistakes repeated |
| Shows humility about the work | Overconfident about skills |
Technical Assessment Approach
Consider a practical exercise that reflects real debt work:
Option 1: Code Review Exercise
Give them a realistic code sample with debt. Ask them to:
- Identify the problems
- Prioritize what to fix first
- Describe how they'd approach the fix
- Estimate the effort and risk
Option 2: Refactoring Exercise
Provide a small, messy codebase and ask them to:
- Add tests to a specific function
- Refactor without changing behavior
- Explain their decision-making process
- Discuss what they would do differently with more time
Team Structure Options
Option 1: Dedicated Tech Debt Team
How it works: 2-4 engineers focused entirely on debt reduction, working across the codebase on strategic improvements.
Pros:
- Deep focus and expertise development
- Can tackle large, cross-cutting concerns
- Clear ownership and accountability
- Easier to measure progress
Cons:
- Risk of isolation from feature teams
- May lack context on business priorities
- Knowledge silos can develop
- Can become a "dumping ground" for unpleasant work
Best for: Large organizations with significant, widespread debt that requires coordinated effort.
Option 2: Embedded Percentage Model
How it works: Every team allocates 15-20% of sprint capacity to debt work. Engineers split time between features and improvement.
Pros:
- Context remains with those who know the code best
- Shared responsibility across the org
- No isolation or knowledge silos
- Debt work becomes normalized
Cons:
- Debt often deprioritized under pressure
- Scattered effort may not address systemic issues
- Hard to tackle large, cross-cutting problems
- Progress is slower and harder to measure
Best for: Organizations with moderate debt distributed across many systems.
Option 3: Rotation Model
How it works: Engineers rotate through focused debt-reduction periods (2-4 weeks), then return to feature work.
Pros:
- Fresh perspectives on old problems
- Knowledge sharing across the org
- No permanent "debt team" stigma
- Engineers develop improvement skills
Cons:
- Context switching overhead
- Progress can be interrupted
- Large projects are hard to complete
- Requires good documentation and handoffs
Best for: Organizations that want to build debt-reduction skills across the team.
Recommended Approach
For most organizations, a hybrid model works best:
- Small dedicated team (2-3 engineers) for systemic, cross-cutting concerns
- Embedded time (10-15%) in feature teams for local debt
- Clear ownership of which debt belongs where
- Regular sync between dedicated team and feature teams
Common Pitfalls
1. Hiring for Rewrite, Not Improvement
The mistake: You hire engineers who want to throw away everything and rebuild from scratch.
What happens: Big rewrites take 2-3x longer than estimated, often fail to launch, and lose the institutional knowledge embedded in the existing system. Meanwhile, the old system still needs maintenance.
Better approach: Hire for incremental improvement. Look for experience with the "strangler fig" pattern—gradually replacing legacy components while the system remains operational. Accept that some legacy code will live forever, and that's okay.
2. Isolating Debt Engineers
The mistake: The debt team works in a corner, disconnected from product priorities and feature teams.
What happens: They fix things that don't matter to the business, lack context for prioritization, and become resentful. Meanwhile, feature teams see debt work as "someone else's problem."
Better approach: Keep debt engineers connected. They should attend product planning, understand business priorities, and collaborate with feature teams. Consider embedding debt specialists temporarily with teams that have the worst problems.
3. No Clear Success Metrics
The mistake: The goal is vaguely "improve code quality" without specific, measurable outcomes.
What happens: Progress is invisible to stakeholders, engineers can't demonstrate value, and funding gets cut when pressure mounts. "We feel like things are better" doesn't survive budget discussions.
Better approach: Define metrics before hiring. Track velocity improvements, bug rates, build times, deployment frequency, or developer satisfaction scores. Show progress monthly. Make the value visible.
4. Treating Debt Work as Punishment
The mistake: Engineers are assigned to debt work because they're underperforming or it's the least desirable rotation.
What happens: The work is done poorly, talented engineers avoid debt projects, and the cultural message is clear: debt work is low-status. Quality suffers.
Better approach: Position debt work as a senior opportunity requiring specific expertise. Hire engineers who genuinely want this work. Celebrate debt reduction wins publicly. Make clear this is critical, valued work—not a penalty box.
5. Underestimating Communication Requirements
The mistake: You hire a brilliant technical engineer who can't explain their work to stakeholders.
What happens: Leadership loses confidence in the investment, engineers can't get time or resources, and the work gets cut. Technical excellence without advocacy is unsustainable.
Better approach: Treat communication as a core requirement, not a nice-to-have. Debt engineers need to translate technical improvements into business value, build stakeholder relationships, and advocate for their work. Interview specifically for this skill.
6. Expecting Immediate Results
The mistake: You hire a debt team and expect dramatic improvements in the first quarter.
What happens: Engineers rush, cut corners, introduce regressions, or burn out. When quick wins don't materialize, leadership loses patience and defunds the initiative.
Better approach: Set realistic timelines. Explain that debt reduction is a marathon, not a sprint. Plan for 6-12 months to see significant results on systemic debt. Celebrate small wins along the way to maintain momentum and stakeholder confidence.