Tech Debt Dilemma: Avoiding the Rewrite Trap

Keeping Our Teams Healthy: Managing Tech Debt and Steering Clear of the Rewrite Trap

We’ve all been in that situation, where a once vibrant, sharp, and motivated engineering team launches a product with tremendous momentum. The excitement is palpable. Features are released rapidly. Customers are delighted. The future feels bright and full of promise.

Then, after a number of sprints, everything seems to slow down, sometimes almost to a crawl. The velocity is no longer what it was. New feature releases become scarce. The bug count climbs, and the quality issues start piling up. The team feels drained, even burned out. Stakeholders grow frustrated, demanding answers about why progress has stalled. And the inevitable whisper floats through the room—"maybe it’s time for a rewrite."

If this story sounds familiar, it’s because this cycle is, unfortunately, all too common.

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Understanding the Downward Spiral

It helps to think of teams as gardens. At the start, the plants (our code and team efforts) are small and thriving, and the weeds (bugs, technical debt) are minimal. But over time, if we don’t tend to the garden carefully—pruning, watering, weeding—it quickly becomes overgrown and unmanageable.

This decline usually boils down to three main causes:

1. Faulty foundational architecture: The original design decisions might have been sound based on initial knowledge but became flawed as requirements evolved.

2. Pressure to ship at all costs: When leadership demands features rapidly, teams often “kick the can” of technical debt down the road.

3. Lack of systemic planning for debt: Without a deliberate, ongoing effort to address tech debt, it accumulates silently and undermines team health.

We’ve seen firsthand that tech debt behaves like a credit card with compounding interest. Small, manageable payments keep things balanced, but letting it grow unchecked leads to bankruptcy—in this case, a team too overwhelmed to ship anything meaningful.

A useful, somewhat objective measure to watch is the ratio of significant features shipped versus the severity and number of bugs outstanding. When feature delivery drops sharply and bugs multiply threefold or more, despite no major changes in team composition, it’s a glaring danger sign.

Striving for a Balance: The “20% Tech Debt” Guideline

One practical takeaway we’ve embraced is to aim for a “stable fulcrum” of approximately 20% tech debt. This means that bug severity weighted by their number should remain about one-fifth of the size and scope of features shipped over the same period. Some level of bugs and technical debt is inevitable—it’s a natural cost of software development.

But exceeding this threshold signals that the team is carrying a heavier load than it can sustain, threatening velocity, quality, and morale. Maintaining this balance isn’t easy, but it’s critical for long-term success.

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The Pillars of Sustaining Team Health

From the insights shared, three habits stand out as pillars to keep teams healthy and the dreaded rewrite at bay:

Habit 1: Continuous Architectural Reviews — Staying Ahead of Complexity

At the outset of any project, architectural reviews are a given. But as deadlines loom and feature demands mount, the discipline to keep reviewing architecture often falls away. This is a costly mistake.

We’ve learned that consistently scheduling architectural reviews for every medium-to-large feature is a powerful preventative measure. The reviews don’t have to be elaborate. A few clear diagrams—sequence flows, entity relationship diagrams, block diagrams—and a concise overview are enough to convey the essential design.

Here’s why this works:

• Shared understanding: When everyone on the team sees how new features fit into the bigger picture, it reduces redundant work and unexpected clashes.

• Early tradeoff discussions: The team can weigh design decisions upfront, preventing costly refactors after code is committed.

• Proactive risk identification: Potential issues related to scale, performance, or stability are caught before they become problems.

• Better onboarding: Having a library of architectural documentation makes it easier for new team members to ramp up quickly.

• Skill development: Junior engineers get mentoring opportunities, learning how to articulate complex systems.

While it may seem like just another meeting, these architectural reviews function as the team’s first line of defense, catching trouble early and saving months of wasted effort.

Habit 2: Bug Backlogs and Relentless Grooming — Listening to the Product’s Pulse

Too often, bug backlogs become “out of sight, out of mind.” Teams avoid the tedious task of grooming bugs, hoping they’ll resolve themselves or get addressed later.

But this is a slippery slope. Bugs are the team’s early warning sirens—signals of pain points in the product or cracks in the process.

Our experience shows that:

• Setting internal bug SLAs (service level agreements) creates clear expectations on how quickly different severities of bugs should be fixed, without the undue pressure of customer-facing deadlines.

• Regular bug grooming sessions every sprint with the right stakeholders involved—not just engineers, but product managers, tech leads, support teams, and these on-call—keep the backlog manageable.

• Assigning bugs to on-call engineers guarantees that fixing and pruning happens continuously, preventing the backlog from ballooning.

• Transparent communication of bug fixes to the wider team via release notes or Slack posts keeps everyone informed and aligned.

This disciplined approach acts like a health check for the product and the team. By tracking the bug load sprint by sprint and balancing it against feature velocity, the team gains valuable visibility into their operational health.

Habit 3: On-Call Rotations — Muscle Memory for Stability

Many teams hesitate to start on-call rotations early, fearing it will distract engineers from feature work. But delaying on-call until the product grows more complex is often counterproductive.

Introducing on-call rotations as soon as the product ships—even if user load is light—builds vital muscle memory. Here’s how on-call benefits the team:

• Structured prioritization: Engineers focus first on incidents, then bugs, then refactoring, and only then features, ensuring stability remains the priority.

• Regular tech debt reduction: The steady pace of fixing and refactoring during on-call rotations keeps tech debt from spiraling.

• Better product stability: Fewer outages, fewer fires to put out, happier internal and external stakeholders.

• Skill leveling: Junior engineers get exposure to diverse parts of the system, accelerating their growth.

• Early warning system: If on-call work becomes overwhelmingly difficult, it signals immediate intervention is needed.

While this practice might reduce feature throughput slightly, the tradeoff is a far more stable product and sustainable team pace.

When (If Ever) to Consider a Rewrite

We get it—starting fresh with a rewrite sounds tempting. The allure of clean code and a greenfield project calls to every engineer.

But the risks are enormous:

• Customers might reject the new product.

• The team could fracture before the rewrite finishes.

• The company’s financial stability could be jeopardized.

• The new architecture may still have unforeseen technical flaws.

That said, there are rare circumstances where a rewrite is warranted:

• Merging multiple products with overlapping capabilities into a single platform.

• When original architecture is fundamentally broken despite best efforts.

• Security or compliance requirements demand a full overhaul.

• The company’s mission has pivoted so drastically that the old product no longer fits.

In these cases, the decision to rewrite should be made with full transparency, careful risk analysis, and alignment across teams.

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Wrapping Up: The Cost of Prevention vs. The Cost of Collapse

All the good habits we’ve described—continuous architectural reviews, rigorous bug grooming, disciplined on-call rotations—take time and discipline. They may slow feature velocity in the short term.

But the alternative—team collapse, product instability, and dreaded rewrites—is far costlier.

Team death leads to attrition, loss of knowledge, and toxic work environments. For smaller companies, it can mean company death.

We hope these reflections encourage you to think proactively about the health of your teams and products. Keep the technical weeds trimmed and the garden thriving.

Invest early in the architecture, listen closely to your bug backlogs, and build sustainable rhythms that support your people and your product.

In the end, it’s not just about code or features—it’s about nurturing the people who build them.

Looking forward to hearing your stories and how you’re managing these challenges.

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