Drowning in Technical Debt?

“Technical Debt” — a term that is often wrapped in mystery, like some cryptic message between engineers and the technology gods. It’s difficult to quantify for executives and financial "decision makers", which makes it even harder to prioritize against everything else the business is trying to achieve.

So what is it exactly? It's probably best explained as a metaphor (I'm not intentionally trying to make it more cryptic, I promise!) Technical debt is sort of like building a house of cards — everything might look stable for now, but one wrong move, like adding new functionality for example, can send everything crashing down. Every shortcut, every delayed upgrade, every "bolt on feature", every ignored bug adds another shaky layer to the structure. Eventually, the weight of old decisions becomes too much, and when the collapse happens, it’s not just an engineering problem — it’s a business catastrophe. The question at this point isn’t if it will fall, but when.

As technology leaders, part of our job is advocating for the real cost of technical debt. But why should we care? If you’ve ever felt like you’re patching holes in a sinking ship, yelling into the void about outdated systems, or walking a tightrope between maintaining old code and shipping new features, welcome to the club.

More importantly though — why should leadership listen?

The Real Cost of Technical Debt

Technical debt usually boils down to two things: risk and money (spoiler alert: both affect the bottom line).

One thing people at all levels of business understand? Dollars. So let’s put technical debt in financial terms:

• Security vulnerabilities – Outdated frameworks and dependencies are an open invitation to hackers. A single breach can cost millions in damages, legal fines, damaged brand and lost customer trust.

• Increased risk of outages – The older and more fragile your system, the more likely it is to collapse. Just ask Southwest Airlines — their outdated scheduling software led to a massive meltdown in December 2022, grounding flights, frustrating thousands, and burning $800 million in the process (ouch) ¹

• Slower development cycles – Legacy code slows everything down. If your team is spending more time wrestling with old code than shipping new features, your competitors are already pulling ahead

• Operational inefficiencies – The longer you ignore the problem, the worse (and more expensive) it gets. Fixing tech debt proactively is actually cheaper than scrambling during a crisis.

Getting Leadership to Care

So... how do you get decision-makers to see technical debt as an actual business threat?

• Make the risk real – “We need to upgrade” doesn’t cut it. Try: “If we don’t upgrade in the next few months, we could face a security breach that costs millions.”

• Show the dollars – Gather metrics. Slow development, outages, and inefficiencies all cost money. Spell it out.

• Bring receipts – Real-world failures like Southwest Airlines' outage prove these risks aren't theoretical. Compare their mistakes to your own risks.

• Push for ongoing investment – Paying down tech debt isn’t a short-term fix — it’s a long-term strategy. Frame it as an investment in keeping systems running, maintaining revenue, and avoiding costly disasters.

The Role of Tech Leaders

Our job isn’t just writing code and maintaining servers — it’s making sure the systems we build don’t turn into expensive liabilities. Therefore, we must take up the torch and make sure we are proactively:

• Identifying weak spots before they become disasters

• Fighting for the resources to keep things running smoothly

• Communicating risks in a way business leaders actually understand

• Ditching the “us vs. them” mindset — when systems fail, everyone loses
  

Technical debt will never fully go away, but ignoring it is the most expensive option. Smart leaders will either invest in a stable, scalable system now — or they (and you) will pay a much bigger price when everything falls apart later.