How to Build an Application Modernization Roadmap

Alexander Kirpichny

Product Owner, Ispirer Systems

Let's face it—technology doesn't stand still, and neither should your business. If you're still relying on aging legacy systems that groan every time you press "Enter," you're not alone. Many companies are caught in the same boat: balancing the need for innovation with the risk of disrupting core operations.

Application modernization is what helps keep this balance.

What is Application Modernization—and Why Should You Care?

Application modernization means updating old software systems to take advantage of modern technologies, like cloud-native, microservices, scalable databases, and secure APIs. It helps businesses move faster, scale, and avoid scary "critical failure" moments caused by outdated code or unsupported platforms.

Why It Matters Now More Than Ever

• 70% of digital transformation projects fail due to poor planning or outdated technology.

• Legacy systems cost up to 15% more annually to maintain.

• 63% of IT decision-makers say legacy systems are a "sustainability nightmare".

So how do you make sure your modernization journey doesn't turn into a multi-year money pit? You build a clear, actionable roadmap: from strategy to execution.

And not alone. Tools like Ispirer's CodeWays and InsightWays make the process smoother and up to 80% faster.

Let's dive into it step by step.

Section 1: Assessing the Current State

Before you take off, you need to know where you're starting from.

Step 1: Take Inventory of What You Have

Create a detailed list of all existing applications, platforms, and databases. It can look like this:

You can also use InsightWays, a free assessment tool, to scan application code, libraries, and database structures and spot:

• Outdated technologies

• Security vulnerabilities

• High-maintenance dependencies

It will also show you which parts of the code can automatically be updated to a new tech so that you can assess the automation potential.

Step 2: Measure Technical Debt

Look at:

• Lines of deprecated code

• Unsupported libraries or frameworks

• Hardcoded business logic

If your app has 50,000 lines of procedural SQL scattered across dozens of stored procedures, you might be sitting on a spaghetti bomb.

Section 2: Defining Objectives and Prioritizing Applications

After the assessment, you may realize that not everything needs to be rebuilt from scratch. So, ask yourself:

• What business goals are driving this? (e.g., Cut costs? Boost performance? Meet compliance?)

• Which apps are really mission-critical?

The RTMI model is a handy framework for making decisions that define the final objectives:

Section 3: Choosing the Right Modernization Strategy

Okay, time to pick your tools. There are six main strategies, often called the "6 Rs":

Then, think again about the parts of the application that you can potentially transfer automatically. With CodeWays, for example, you can auto-convert some application code from, say, Delphi to Java or C#, saving hundreds of hours.

Section 4: Designing and Planning the Roadmap

You've assessed your legacy systems, set your priorities, and chosen your strategies. Now, it's time to build a more detailed step-by-step plan.

Break It Down into Phases

Let's avoid chaos by tackling this in bite-sized chunks. A solid roadmap typically includes the following phases:

1. Discovery & planning. Again, tools like InsightWays to deeply analyze your applications and databases. Document dependencies, identify blockers, and engage stakeholders across IT, security, operations, and even HR.

2. Pilot modernization. Choose a small and non-critical app with moderate complexity. It will act as your sandbox for experimenting with tools, testing strategies, and learning lessons with no risk for the business. It's also a great way to win early buy-in from leadership, if you're not the one approving the modernization. Plus, at this and the following stage, you'll want to plan which parts of the application will be updated automatically to the new tech with CodeWays.

3. Full modernization. Once your pilot succeeds, roll out the approach across prioritized apps. Use a phased or wave-based deployment and focus on high-impact applications first. These have the biggest business or performance value.

4. Testing & optimization. It's best to perform multiple rounds of testing: automated and manual. Load tests, user acceptance testing (UAT), security scans, and performance tuning are non-negotiable.

5. Deployment & training. Deploy in production, but also make sure your users and support teams are trained and confident.

And don't forget documentation! A beautifully modernized system is useless if no one knows how to use it.

Many legacy apps are also tangled in complex system integrations. It's a good idea to decide where you can use APIs, middleware, or microservices to bridge old and new components during the transition.

Read more: Modernization vs. Migration: Databases, Applications & Cloud

Section 5: Implementation and Execution

Yes, things can get messy at this stage. But with the right approach and tools, you’ll stay in control. You already have your phases, and it's time to go through each of them.

At the implementation stage, you can take the full advantage of CodeWays. If you have dedicated engineers, they can perform and control the setup for partial automation of code updates. If not, it's better to hire an expert team that can even plan the entire process for you and assist in prioritization

Thus, you will avoid becoming a part of the 70% of digital transformations that failed.

Read more: 11 Reasons Why Companies Fail at Cloud Migration and How to Succeed

Section 6: Monitoring Progress and Continuous Improvement

Modernization doesn't end at deployment, though. In fact, the most successful companies treat it as a continuous cycle of optimization and learning. These companies track the right KPIs to know exactly how the app modernization process goes:

Read more: Migrating to the Cloud Without Downtime: The Complete Checklist

Section 7: Overcoming Challenges

Finally, even with the best roadmap, bumps in the road are inevitable. The good news is that most of them are predictable and avoidable with the right mindset and tools. We've made a quick cheat sheet on what you need to anticipate:

Not sure you'll get it done? Lean on Ispirer's support services for application modernization planning, troubleshooting, and even customized automation logic. Our experts will help you translate tech goals into real-world business outcomes!