There’s a fine line between stability and stagnation.
Tech leaders are constantly weighing the tradeoff between building what’s next and maintaining what’s already in place. But the longer “good enough” lingers, the more it drains your velocity, your talent, and your edge.
So how do you know when to modernize – and when it’s time to move on entirely?
Why Companies Wait – and What It Costs
The reasons for sticking with legacy systems are rarely irrational. Migrating a platform or reworking infrastructure feels risky. The cost is upfront, the disruption is real, and the ROI isn’t always immediate. But the risk of standing still? That’s often harder to see and quantify – until it’s too late.
Ask yourself:
- Are your engineers spending more time maintaining than building? Consider: Do you devote significant capacity to maintenance vs. net new development?
- Do new features feel like a gamble every time you deploy – or worse, like a mountain of effort for something that should be simple?
- Have you lost great talent who got bored or frustrated with your tech stack?
It’s not just you. According to a recent IDC report, developers spend less than 16% of their time actually building new applications. The rest? It’s consumed by operational drag—setting up CI/CD pipelines, triaging performance issues, digging through undocumented legacy code, and struggling with tool compatibility that should’ve been solved two architectures ago.
Often, this isn’t a sign of poor engineering, it’s a sign of systems that haven’t kept up. Modernization is about more than speed – it’s about removing the hidden friction that eats away at your team’s focus.
Warning Signs You’re Overdue
Modernization doesn’t start with a catastrophe, it starts with these quiet signals:
- Your devs are shipping hotfixes instead of features.
- Product and engineering teams are duct-taping systems just to make them talk.
- Onboarding new engineers feels like boot camp for legacy tooling.
- Customers are asking why something “so basic” isn’t possible or takes an incredible amount of time.
These aren’t just annoyances. They’re signs that your systems are blocking progress and that the problem is getting worse.
What “Modernization” Actually Means
Let’s clear something up: modernization doesn’t mean ripping everything out and starting from scratch.
Sometimes it’s breaking apart a monolith into services. Other times it’s moving key workloads to the cloud or refactoring the parts of your stack that are holding you back. There’s nuance here – and that’s where good engineering strategy shines.
One helpful concept is the Strangler Fig Pattern, coined by Martin Fowler. It’s a method of replacing a legacy system piece by piece, slowly “strangling” the old system out of existence. It’s not sexy. But it works.
Building a Business Case That Actually Lands
Modernization isn’t just a technical conversation – it’s a business decision. To get buy-in, tech leaders need to shift the conversation from “We need to upgrade XYZ” to “Here’s what we can do if we don’t.”
That might mean:
- Cutting time-to-market from months to weeks
- Reducing the cost of outages
- Making your company more attractive to top engineering talent
Here’s a real-world example:
An Entertainment Rights Management Software Company needed to overhaul an aging platform – specifically, a dated UI and brittle backend – without pausing day-to-day operations or risking revenue loss. Distillery architected a phased modernization strategy:
- First, we built a completely new front-end from scratch
- Once the UI was 80% complete, we began modernizing the backend and deployment layers
- The legacy system remained fully operational throughout the process
The outcome? A faster, more intuitive, and visually modern product that not only improved the customer experience but also supported the business through two acquisitions. The platform remains active and continues evolving, proving that modernization doesn’t have to come at the cost of business continuity.
You don’t need to tear everything down to build something better. With the right strategy, you can modernize in motion – no disruption required.
The Cost of Waiting vs. the ROI of Change
Let’s be honest: most companies don’t modernize because they want to. They do it because they have to. They get acquired. A new leader comes in. Or – worst case – something breaks that can’t be patched anymore.
But by then, the price tag is higher.
Consider this: delaying modernization doesn’t just cost more in the long run; it can also undermine your competitive edge. While you’re babysitting outdated systems, your competitors are building better user experiences, shipping faster, and attracting stronger teams.
McKinsey has found that companies who lead in digital modernization outperform laggards in revenue growth by over 5x. That’s not fluff – it’s survival.
So… When Is the Right Time to Leap?
There’s no perfect time. But there is a right mindset: anticipation over reaction.
If your systems are already holding back your roadmap, or your best engineers are quietly interviewing elsewhere, you’re past due.
And if you’re on the fence? Consider this your sign. Because the gap between “working” and “working well” is where growth dies.
Modernization Doesn’t Have to Be a Leap of Faith
At Distillery, we’ve worked with companies across industries to assess what modernization should actually look like for their goals. Whether it’s cloud migration, performance optimization, or refactoring for scale, we help engineering leaders move forward with confidence.
Curious what that might look like for you? Talk to us. Or check out how we’ve helped clients drive growth through smarter systems.