Managing Technical Debt - A Strategic Approach

Technical debt isn't inherently bad—it's a tool. The key is managing it strategically rather than letting it manage you.

Authored by: Steven Alan Wilson

Tags:Technical DebtSoftware ArchitectureEngineering LeadershipStrategy

Managing Technical Debt - A Strategic Approach

Reframing the Conversation:

Early in my leadership journey, I made the mistake of treating all technical debt as the enemy. I pushed teams to eliminate it completely, which led to over-engineering and analysis paralysis.

Then I realized: technical debt is like financial debt. Sometimes taking on debt is the smart choice—if you manage it strategically.

The Strategic Framework:

I developed a framework that changed how we approached technical debt:

Categorize Intentionally: We started labeling debt as either "strategic" (chosen for speed) or "accidental" (created through lack of knowledge or care). This simple distinction changed our conversations.

Quantify the Interest: For each piece of debt, we estimated the ongoing cost—slower feature development, increased bugs, team frustration. This made the invisible visible.

Track and Communicate: We created a technical debt register that was visible to product stakeholders. This transparency led to better-informed prioritization decisions.

The Balance:

Finding the right balance meant:

Strategic Shortcuts: Sometimes shipping with technical debt was the right call. We'd document it, understand the cost, and plan the payback.

The 20% Rule: We allocated 20% of each sprint to debt reduction. Not in a separate sprint, but continuously. This kept the codebase healthy without stopping feature development.

Debt Days: Once a quarter, the entire team would focus exclusively on paying down debt. These were some of our most productive and energizing days.

The Results:

This approach delivered remarkable outcomes:

Faster Delivery: Paradoxically, by accepting some debt, we delivered faster. The key was choosing which debt to take on.

Better Morale: Engineers appreciated having dedicated time for quality. The codebase stopped feeling like a burden.

Stakeholder Trust: By making debt visible and showing consistent paydown, we earned trust to make technical decisions.

The Lesson:

Technical debt isn't a failure—it's a choice. The failure is in making that choice unconsciously or failing to pay it back. Treat it like financial debt: borrow intentionally, track the interest, and pay it down systematically.

About the Author

Hi, I'm Steven Alan Wilson, a Digital, Technical, and AI Leader with over 20 years of experience helping organizations build exceptional digital products and high-performing teams.

I share insights on leadership, technical strategy, and building great teams. Welcome to my corner of the internet.