The Executive's Guide to Technical Debt

No. Technical debt is an inevitable part of building software, just as financial debt is a normal part of running a business. Ward Cunningham coined the term to describe the trade-off between shipping quickly and building perfectly. Every successful company carries some debt - the question is whether you are managing it intentionally or ignoring it until it becomes a crisis. Bad engineering can create debt, but so can smart strategic decisions like launching an MVP or pivoting quickly.

Watch for these warning signs: feature delivery is slowing despite stable or growing headcount, the same systems cause repeated incidents, engineers are leaving and citing "legacy code" in exit interviews, simple changes require weeks instead of days, and your team avoids touching certain parts of the codebase entirely. If three or more of these apply, your debt is likely at a level that requires dedicated investment, not just incremental improvement.

It depends on the severity. For moderate debt, embedding 15-20% capacity within existing teams works better because the people who know the code best are the ones improving it. For critical debt in specific systems, a temporary "tiger team" of 3-5 senior engineers can make concentrated progress. Avoid creating a permanent debt team - it sends the message that debt is someone else's problem and removes accountability from the teams creating it.

At 15% of engineering capacity, most teams see measurable improvement within 2-3 quarters. The first results are usually reduced incident frequency and faster onboarding, followed by improved feature velocity. Below 10%, you are typically just keeping debt from getting worse without actually reducing it. The key is consistency - a sustained 15% allocation beats a one-time "debt sprint" every time because it builds the muscle memory and culture of continuous improvement.

Use the financial metaphor directly: "We took out loans to ship faster. Those loans have interest. If we do not make payments, the interest compounds and eventually we cannot ship at all." Then translate to their language: show the impact on time-to-market, customer satisfaction, security risk, and talent retention. Never present it as a technical problem - present it as a business risk with a measurable remediation plan. Our board presentation guide has slide-by-slide templates.

Technical debt compounds. Today's 33% maintenance overhead becomes 50%, then 70%. Feature delivery slows to a crawl. Your best engineers leave for companies with modern stacks. Security vulnerabilities accumulate in systems nobody dares to update. Eventually you face the most expensive option of all: a full rewrite or replacement, which costs 5-10x what incremental remediation would have cost. The companies that ignore tech debt do not fail suddenly - they slowly lose the ability to compete until a more agile competitor takes their market.