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When’s the best time to upgrade your tech stack?

Before your legacy tech becomes a liability.

“Companies that have adopted a digital-first mindset have a recruiting advantage—they’re able to provide the tools that offer simplicity and make employees’ jobs less stressful.”1
—Fortune

Like getting married or having kids, there’s never a “perfect” time to replace your legacy technology with more advanced enterprise solutions. The mere thought of it is daunting and overwhelming. It’s comforting to fall into an “if it ain’t broke, don’t fix it” mindset, especially when your staff and budgets are maxed out.

There’s nothing wrong with hanging onto your systems if they work well, protect your assets and don’t impede growth. But at some point, your legacy IT will become a liability. In an ideal world, you’d upgrade before then. So how do you know when “then” is? Consider the risks of sticking with legacy tech vs. the rewards of adopting a digital-first mindset with advanced enterprise technology.

Reward of upgrading: Keep employees productive—and keep employees
Risk of waiting: Frustrated employees lose interest and loyalty

You know who suffers most when you try to extend the life of dated technology? Your people. Slow, cumbersome apps are kryptonite to productivity and innovation. Even worse: The frustration and stress of waiting for lags, buffering and unresponsive programs can chip away at the satisfaction and joy of meaningful work. To employees, it feels like the company doesn’t care enough to invest in the tools to make the most of their skill sets. And in today’s tight labor market, you want to do everything you can to keep employees feeling valued and satisfied.

Consider this: 41% of Gen Z enterprise workers are unhappy with their job and more than 50% will look for a new one in the next year.6 Why? Because they spend too much time on menial tasks—a third of the work week7—and they know there are simpler, more efficient ways of working.

Reward of upgrading: Attract top talent
Risk of waiting: Being short-staffed and unable to recruit skilled employees

To compete for the best candidates, you have to offer the best technology. Job seekers want the freedom and flexibility to work on their own schedules, from anywhere. They want tools that minimize mundane work and free them for more rewarding activities. And that means embracing a digital-first mindset with technology that supports Unified Communications, advanced voice systems, and applications that allow people to collaborate, be productive and access your network securely from everywhere.

Reward of upgrading: Free your team, cut maintenance costs
Risk of waiting: Wasting time and money on equipment maintenance

It takes longer and is more expensive to maintain, fix and update legacy technology. The components are costly, often difficult to source and the work needs to be done on site. Many legacy systems aren’t even supported by the manufacturer anymore. When they are, you have to continually update to keep them functional—and it’s not so easy. Even a small adjustment eats up time and resources.

In contrast, modern IT solutions like SD-WAN can be provisioned and implemented remotely, upgraded and scaled easily and automatically, and monitored and maintained from a central location. Your IT team’s time is money, and when you upgrade technology, you free up time.

Reward of upgrading: Secure your network and stay in compliance
Risk of waiting: Devastating damage from a cyberattack, fines for incompliance

Legacy systems simply don’t have the capabilities and intelligence to detect and prevent cyberattacks. Security updates are rarely available. Without basic protections like intrusion detection and business firewall services, your network is riddled with vulnerabilities. Even scarier: Cyber villains know you’re using solutions that are no longer supported by the vendor and can stealthily aim attacks at the unprotected apps.

Advanced enterprise solutions include continually updated defenses, like Managed Firewall and remote monitoring, to help identify and avert issues before they escalate. These protections are critical in compliance-heavy industries, like government, healthcare and financial services. 

Reward of upgrading: Delight customers and gain market share  
Risk of waiting: Falling behind the competition

Customer expectations are continually growing and changing. To keep up, you need to continually adapt your processes to offer ever-more-convenient ways of working with you. If it’s not easy to interact with your business, customers will go elsewhere. Problem is, legacy systems are rigid. They’re difficult and time-consuming to upgrade and are often incompatible with new capabilities. In contrast, enterprise solutions are adaptable by design, making it easy to scale and integrate new apps and features with minimal resources.

When’s the right time to upgrade legacy technology? Before the risks become realities.

For the past five years, replacing legacy apps has been a top 10 IT spend.2 Why? Because limping along with legacy technology, creating workarounds and adding third-party solutions are useful band-aids. But they aren’t long-term solutions. Sooner or later, you’ll need to replace your end-of-life systems. Preferably before they frustrate team members and customers and put your network and business at risk.

So why not upgrade now? Rather than waste resources and risk vulnerabilities on temporary fixes, start reaping the rewards of a digital-first solution as soon as possible.


Replace your legacy tech before it becomes a liability. Contact our Enterprise Tech Experts to help you assess your risk-to-reward ratio.


1 gartner.com/smarterwithgartner/7-options-to-modernize-legacy-systems
2 trends.simnet.org/trends-study-archive