Technical Debt Assessment: A Practical Checklist
A structured framework for assessing technical debt, covering code, infrastructure, processes, and knowledge. Includes a scoring model for prioritisation.
A structured framework for assessing technical debt, covering code, infrastructure, processes, and knowledge. Includes a scoring model for prioritisation.
Who this is for
Technical leaders who know their systems have accumulated technical debt, but need a structured way to assess, quantify, and prioritise what to address.
Question this answers
How bad is our technical debt really, and what should we fix first?
What you'll leave with
Technical debt is the accumulated cost of shortcuts, deferred maintenance, and outdated decisions in your technology systems. Like financial debt, it compounds. Small amounts are manageable, but unchecked accumulation eventually constrains everything you try to do.
It's not just about messy code. Technical debt includes:
Every business with software has technical debt. The question isn't whether you have it; it's how much, where, and what to do about it.
Most businesses know they have technical debt. What they lack is a structured view of how much, where it sits, and what to prioritise. Without this, technical debt gets addressed reactively, fixing things only when they break, which is the most expensive approach.
A structured assessment gives you:
We assess technical debt across four dimensions. Each dimension has specific checklist items rated on risk (likelihood of causing a problem) and impact (severity when it does).
This is what most people think of as technical debt, code quality, architecture decisions, and design patterns.
The platforms, servers, and environments your systems run on.
The tools, workflows, and practices that your team uses to build, test, and deploy software.
What people know and what's documented. Often overlooked, but one of the most dangerous types of debt.
For each checked item, assign a score:
| Low impact | High impact | |
|---|---|---|
| Low risk | 1, Accept it | 2, Plan to address |
| High risk | 2, Plan to address | 3, Address now |
Risk = how likely is this to cause a problem in the next 12 months?
Impact = if it does cause a problem, how severe is the business impact?
Sum your scores across all dimensions. This gives you a total debt burden and, more importantly, a prioritised list of what to address first.
"We need to restructure the order module" means nothing to a finance manager. Put it in business terms instead.
Put your own numbers against each one where you can. A rough estimate from your own time records is more convincing than "the code is hard to work with".
Some debt is normal. A business with none would never ship anything quickly. The aim is debt you know about, are paying down at a steady rate, and that is not blocking the work that matters.
Yes. Taking a shortcut on purpose to meet a deadline is a fair decision. The key words are "on purpose" and "written down". Trouble starts when debt builds up quietly.
Chip away, almost always. Big clean-up projects are hard to justify and are often cancelled halfway when priorities shift. Leaving each part a little better every time you touch it is steadier and less disruptive.
When keeping it running costs more than building or buying a replacement, or every change is slow and risky. Our legacy system migration guide covers how to move without breaking what works.
Run through the checklists above with your development team. Score each item, sort by priority, and pick the top 3–5 items to address in the next quarter.
If you'd like an independent assessment, book a technical audit with our team. We'll review your systems, quantify the debt, and give you a prioritised remediation plan, including honest advice about what to fix, what to live with, and what to replace.
Meet the person
This guide comes from real projects. If it raises a question about your own system, you can ask the founder directly.
HELLO PEOPLE designs, builds and looks after AI, software, app and data solutions for Australian businesses, with senior expertise on every project and a scope agreed before work starts. For an older system, that means learning what it really does first, so nothing your business relies on is lost.
Since 2007, HELLO PEOPLE has delivered more than 100 projects from Perth for small and medium businesses across Australia: custom software and apps, system integrations, data migrations, reporting and dashboards, and AI that works inside the systems a business already runs.
I lead every engagement myself. I trained in accounting before moving into IT, hold accounting and IT professional qualifications and an MBA, and bring more than 20 years of experience across sales, service delivery, inventory and compliance. I am also a PhD candidate in AI at Curtin University, researching retrieval-augmented generation (RAG), so the technology is always judged by what it does for the business.
Small and boutique. The person who scopes the work is the person who does it, and the same person is there when the old system is switched off.
No ticket queue and no account manager in between. You hear back within one business day, usually sooner.
The upgrade is the start, not the end. When you need the next system, integration or report, you call the same person, who already knows your business.
Ask the author
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Kasun Wijayamanna
Founder, replies within one business day
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