Why are companies not tackling their Windows technical debt?

The much discussed Windows 10 end-of-support deadline finally passed in October. There was, and still is, a big push to generate awareness around the need to upgrade devices still running on Windows 10, which are now susceptible to security risks.

But it seems even if organizations weren’t aware of end-of-support deadlines (which they should be), they do seem to be aware of the many issues and risks technical debt poses.

Jonathan Dedman

That means they are accruing a variety of operational, performance and compliance risks from maintaining outdated systems.

Notably, half of the leaders surveyed said they had experienced system downtime that was linked to technical debt.

Despite this, there seems to be a major disconnect between awareness and action. Even though there is widespread acknowledgement of technical debt and its challenges, only a fraction – 14% – of respondents are prioritizing fixing and upgrading legacy systems in the next year.

The leaders surveyed were from government, finance and manufacturing. These are high-risk sectors, often with vast and complex IT estates, making modernization a major and costly activity.

But given the scale of the problem and the risks that come from technical debt, you would think more would be proactively addressing the issue.

So, why are so many not tackling their technical debt? And what methods could help them overcome any challenges they may be facing?

software, the task of solving technical debt can seem momentous. This is potentially why many companies avoid their debt but, in doing so, leave it building.

The most obvious avoidance factor would be the time and cost of modernizing outdated applications, especially in a climate of reduced budgets and external economic pressures. Just under half of those surveyed (45%) said these two factors were prohibitive to confronting their technical debt.

But the actual practicalities of modernizing bespoke Windows applications can be challenging too.

Many legacy applications have hardcoded and specific operating system (OS) dependencies that traditional migration methods like containerization and virtualization struggle to account for – these business-critical apps aren’t designed for modern OS environments.

So, this could explain why 30% of leaders leave systems as they are, because they are scared of “breaking something”.

Crucially, the threat of downtime is ever present, and these high-risk sectors can’t afford any disruption to their services. Yet running their applications in legacy Windows environments can lead to downtime too. So, it’s a catch-22 situation: downtime can occur from both upgrading applications and leaving them unsupported.

A combination of these reasons is likely influencing strategy. Forty-six per cent of companies are happy to leave systems as they are and only address technical debt reactively after problems occur.

But it works the other way round too. There is also the idea of wanting the latest technology and being too ‘future-focused’. A common theme we hear at the moment is that “if it doesn’t have AI, we don’t want to invest”.

It’s a completely understandable viewpoint – innovation drives profit. But building a strong foundation to move forward is critical to being able to innovate. Without it, new technologies simply won’t work to good effect and security and compliance risks will remain high.

Paying off technical debt

So, what are some of the solutions?

To get things on track and solve urgent technical debt issues (like using Windows 10 devices), an immediate modernization project will be required. But it’s unlikely you’ll be able to pay off all of your technical debt in one go.

In fact, a major overhaul of systems can create risks of its own. The smarter approach is to implement cost-effective and incremental changes that start paying off technical debt bit by bit.

Not only does this reduce risks, but it creates a company mindset of continuous modernization that will prevent technical debt from emerging again.

For example, aligning budgets and resources with end-of-support deadlines so that devices are gradually upgraded with enough time to spare.

This mindset can be driven by awareness of what tools and strategies are able to cost-effectively tackle technical debt with very minimal disruption.

IT infrastructure without altering the behavior of the applications themselves.

Automation capabilities can then monitor and track for risks like drift over time to support an ongoing strategy. In this position, firms are far better placed to integrate newer technologies like AI.

Targeted upskilling for using both new technologies and legacy systems is also crucial to ensuring skills gaps are reduced and there is knowledge at both ends of the spectrum.

And incentivizing buy-in from the C-suite by explaining the risks of technical debt is key to building a clear and funded transformation roadmap to eliminating it – promisingly, 39% have done this.

Less debt, more freedom

Windows technical debt is widespread. But while many are aware of the risks and costs this creates for them, they face blockers in taking action and eliminating their debt.

Clearly, there’s a mindset issue to overcome, and companies need to prioritize the task in hand. Cultivating this mindset comes from understanding why blockers exist and the tools and strategies available to overcome them.

By building modern IT infrastructure, companies gain operational freedom and the springboard to innovate further. To reach this desirable position, they must tackle their Windows technical debt first.