Modernizing legacy applications can be daunting, especially since legacy applications tend to grow in complexity over time and have multiple dependencies on other enterprise systems. In a recent survey, 71% of respondents reported that legacy modernization efforts were stressful1. Fear of failure from previous attempts has increased IT leaders’ fear of harming their careers. Culprits of failed modernization span the gamut – from misaligned expectations and costly strategy missteps to hard-to-find resources and tools that can provide the right knowledge and capabilities. At the same time, it is clear that organizations must grow and transform to enhance innovation potential, improve internal and external experiences, and reduce risk and costs. Cracking the code on the best legacy modernization approach is therefore essential.
As the saying goes, all seemingly intractable problems can be untangled by breaking them apart in ways that still make sense and tackling them in smaller doses. In fact, mapping out modernization projects in phases empowers every organization on its modernization journey to achieve success without drowning in the time and resource costs of failures. By continuously aligning with business stakeholders, thoroughly reviewing systems, zeroing in on specific modernization paths, and using a test or pilot project prior to scaling, IT teams can finally crack the code of successful application modernization.
Here’s a tried-and-true roadmap for the best legacy modernization approach for your team, outlining the critical steps:

Step 1: Align on goals with business stakeholders and take stock of your organizational constraints
When you start the initial planning for your modernization project, work with key stakeholders on what the business goals are that the modernization project needs to address and different ways in which those goals can be achieved. Typically, this will take the shape of either a business transformation, technology transformation, or both. Then, take stock of your constraints: people, processes and budget. Consider who needs to be involved during the process, such as business and technical stakeholders, and resources that will be required for the project. Budget, resource or time constraints may dictate if you can pursue a business transformation or if you need to focus only on a technology transformation to start.
More questions to consider include: What is the timeline for modernization, and how quickly do you need to show results? Do you need to embark on a major transformation initiative or do only certain systems need to be addressed? How will you measure the success of the project? What is your available budget? Taking stock of your initial requirements and constraints will help you identify key considerations as you determine your ideal path to modernization.
Step 2: Assess your legacy applications, including critical dependencies
The next step is to assess your legacy applications thoroughly. Review the source code and generate an up-to-date list of documentation artifacts to understand the logic, complexity and dependencies within the applications. This documentation process will reveal the software’s complexity as well as dead or redundant code that is surely lurking inside. The output at this stage is a series of reports, diagrams, and logic representations that provide a detailed view into the composition, database access details, and logic of the applications processed. These artifacts give you necessary information to categorize the current state of your applications, estimate the investments needed to determine your transformation options and help outline the business value associated with each option. This step also allows you to see how you could break up the modernization process across multiple applications, i.e. which modules have dependencies and which don’t.
Using manual methods, the effort required for documentation and analysis of your applications can be significant. This is where your team can benefit from intelligent automation. There are tools out there that can automate the reverse engineering of your source code and produce documentation artifacts for you. For example, the Intellisys platform reduces the time to create documentation by 90% or more using its patented technology. This documentation provides both graphical and non-graphical artifacts allowing both technical and business analyst resources to dive deep into understanding the inner workings and complexity of their systems. Using that knowledge, they can estimate the investments needed to achieve the business value associated with the outlined modernization goals.
Step 3: Determine the best legacy modernization approach(es) for you
Every enterprise system is unique, so determining the type of modernization you want to implement for each system that needs it is a vital step in the modernization process. The most common modernization options fall into five broad categories – Retain, Migrate As-Is, Optimize & Migrate, Reimagine & Redesign, or Retire. Here’s a quick visual to describe these options:

- Retain: Use this path for an application where no changes are needed for business processes, that has few dependencies, and/or can be supported using modern technology
- Migrate As-Is: This is one of two technology transformation options. Use this path for an application where code/rule/architecture optimizations are not essential prior to migration or where there are significant benefits to moving the application immediately.
- Optimize & Migrate: This is the second of the technology transformation options. Use this path for an application where minor code/architecture optimizations are essential prior to migration.
- Reimagine & Redesign: This is a business transformation path. Use it for an application where there are significant policy and technology changes that need to happen to meet business goals moving forward.
- Retire: This path can also be part of a business transformation. Use it for an application that has duplicate functionality with another or no longer makes sense for business goals moving forward.
Determine the path that best fits your organization’s needs and integrate it into your planning. To learn more about these approaches and how to choose between them, download our application modernization strategy and planning guide.
Step 4: Start small with a pilot project
Create a small, clearly defined project to test your process, such as modernizing a single component of the application. Apply your modernization process to this small project to validate your planning, communication, and expected results. The test project will help you identify any flaws in your process and enable you to course-correct before embarking on a full-scale modernization project. Take what you’ve learned, integrate it into the larger plan, then run another test to confirm the process works as you planned.
Conducting small, quick tests will verify which processes work and are repeatable and will save resources, pitfalls, and hidden risks in the larger project. It may also help you confirm whether your vendors are a good fit for the initiative. If a vendor fails to perform as expected during the test project, use it as an opportunity to clear up any requirements, or to consider finding a new vendor.
At this point, you should have a clear understanding of what it will take to complete your modernization project. During this and any of the previous two steps, regroup with the key stakeholders and revise their expectations based on the revealed complexity, risks, and resources (both internal and external) needed to successfully complete the project. Include revised cross-organizational dependencies, budget projections, and timeline.
Rewrite the deliverables and timing for each phase of the modernization process. Mapping out your current state, available resources, and expectations will help you avoid mismatches between capabilities and expected outcomes- a common pitfall in application modernization projects.
Step 5: Scale with confidence
Upon completion of a successful pilot or pilot projects, scale the initiative to achieve your full transformation goals.
Throughout all these phases, embrace automation over manual processes. Automation enables IT teams to implement modernization initiatives on a larger scale, consistently, and minimizes the risk of errors, at a fraction of the cost and time that manual processes take. Automation also enables organizations to more quickly test and understand if a modernization approach will meet their needs. Organizations can iterate and adapt prior to starting a large-scale effort, using the pilot phase. Once this evaluation is done, the rest of the phases can be more successful because you have the learnings from the proof of concept step.
Consider these automation benefits: a multi-billion dollar investment firm turned to Intellisys to automate the reverse engineering and migration of an AS400 COBOL transactional system to Java and PL/SQL. To start, they were able to extract meta-data from 151,000 lines of COBOL code in two weeks, which, in turn, empowered the organization to analyze and optimize the extracted meta-data in four weeks. At the end, just under 90% of the COBOL code was transformed automatically, with the remaining code requiring manual completion.
To learn more about how EvolveWare can help you define the best legacy modernization approach to meet your goals, schedule a consultation with our expert team.
1 Mechanical Orchard Research Report. (2024 September). “Legacy Issues: What IT leaders really think about modernization.” Retrieved (2024/09/26). From https://www.ciodive.com/press-release/20240829-enterprise-it-leaders-twice-as-likely-as-juniors-to-delay-advocating-for-le-1/



