Member-only story
From Technical Debt to Technical Health with HealthCheck
Why software fails and how you can practically address it with a six-step plan

It is common for software-producing teams to struggle with their business counterparts when it comes to technical debt. If you’ve ever built a software system or product, have been hampered by how hard it is to evolve it at the expected rate, and subsequently tried to argue for allocating time for accrued technical debt, then you might have heard one or more of these at some point:
- “Why didn’t you build it right the first time?”
- “I don’t think you need that.”
- “I don’t have those issues!”
- “You’re just taking the piss, aren’t you?”
- “We don’t have time nor money for nice-to-haves right now…”
- “Is this actually a problem or are you just gold-plating the damn thing?”
- “So now you want more money to do what you failed to do the first time around!?”
- “Christ almighty, don’t go telling management about this!”
Let’s be clear: Unless you own the budget, you’ll never have absolute leverage in this (or any) situation. And, unfortunately, there will not come an opportunity in which there is suddenly time and money to do these activities—you’ll probably get the hint already in the intonation and delivery of the statement from your counterpart! How on Earth do we align on the necessity of addressing the technical debt damaging our team and product?!
In this article, I’ll propose a way to understand technical debt and make it a concrete, meaningful notion for all involved parties—one that is possible to quantify, qualify, and solve. We’ll round off with a six-step strategy to tackle technical debt, including running a HealthCheck review and offering a way to calculate your technical debt.
After reading, I hope those of you in the “business” track can better understand the nature and pedigree of technical debt and consider why it’s wise to repay it and that those of you closer to the technology will be able to quantify risks and costs involved with unrestrained technical debt.