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5 Tips For Avoiding Roadblocks in Legacy Application Modernization

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There’s no one size fits all solution to application migration. However, with a detailed plan and thought-out legacy modernization approach, you can avoid roadblocks and common pitfalls. In our experience, these are the issues that tend to get overlooked or grossly underestimated when modernizing legacy applications and systems.

Tip #1: Identify Entangled Dependencies

Far too often, organizations begin an app modernization effort without considering the impacts to other applications and systems. An unexpected dependency can bring an entire migration project to a halt. It is essential to understand each app’s dependencies and how to manage them when moving to the cloud. 

Application migration often involves various teams across areas of a company, but the people who understand the dependencies might not initially be the ones involved in the application modernization project. Since different areas of the business might have competing agendas or priorities related to the app migration or timing, it’s important to consult with everyone that might be impacted. Ensure the right resources come together—when technical and business stakeholders work together, often multiple solutions for managing interdependencies emerge.

When we engage with clients for cloud migration projects, we ask the team what other applications rely on the data from each application we’re evaluating. Will there be latency if one app is on-prem and one is on the cloud? If we put that app in the cloud does the data warehouse also need to be in the cloud? Asking these types of questions can unearth hidden dependencies and considerations. Figure out the right set of architecture principles that will be important to consider. Underestimating application dependencies can be a serious roadblock if not mitigated ahead of time. 

Tip #2: Avoid Enterprise Governance Gridlock 

One overlooked roadblock that we often see when determining how to migrate legacy applications to the cloud is inflexible governance. At larger organizations, sometimes governance can get in the way of progress. Watch out for networking, security, and architectural guidelines that may be at odds with your intended migration plan. For example, one of our clients had a group of architects overseeing application architecture governance, another team doing data security (for HIPAA compliance, credit card compliance, etc.), another team that secures the network perimeter, and so on, and each had its own governance plan. Sometimes these plans were at odds with each other, which hindered progress when attempting to comply with conflicting guidelines. The solution was to establish oversight with a unifying group to resolve conflicts and set up collaborative structures for enterprise governance.

We approach technology governance with three ascending categories: boundaries, fences, and iron bars. This allows for a more flexible tiered approach to restrictions, security, permissions, and other governance structures. If your company’s enterprise governance is too rigid to get anything done, your teams may need to negotiate to avoid unmitigated gridlock. 


Tip #3: Get Ahead of Networking Conundrums

Legacy applications have a higher chance of security issues that if not considered before migration could have serious impacts when migrated to the cloud. A complicated corporate network is often overlooked because it’s like air—it’s everywhere, but you don’t see it. Things like asymmetric routing issues, or firewall, gateway, and certificate issues can be difficult to troubleshoot when they are discovered during migration instead of being planned in advance. Together they can seriously impede progress towards a successful application migration. 

The change to cloud might make a significant difference in the way regulatory compliance is handled, or the ways data is managed across applications. Technical debt in the corporate network such as illicit use of public IPs or unencrypted communication can cause glaring security gaps. Planning for and uncovering potential network issues early can prevent security and legal troubles and promote a smooth cloud application migration


Tip #4: Ensure Cloud Compatibility

When creating a legacy application modernization strategy, cloud-readiness of code and architecture must be considered. Some of our clients have struggled with key elements of cloud migration planning such as timing and prioritization. They might not be looking at the big picture of their migration, or they might be focusing too much on specific details—this is where our app modernization roadmap is most useful. 

Assessing each app for cloud compatibility may be a deciding factor in when, if at all, an app is migrated. For example downlevel .NET apps may require significant code changes to containerize. Existing monitoring or logging technologies may be antiquated or unworkable in the cloud. For some legacy applications, it may be too costly or too time-consuming to be practical to migrate. Understand not only which applications will have the most benefit in the cloud, but which are the most ready or will be the most efficient to migrate when making your modernization plan.


Tip #5: Find Business Value and Prioritize the Portfolio

Some of our clients find themselves with too many applications to move in a single phase of migration—they don’t know where to start, or they’re staring down a budgeting and a prioritization issue. They struggle to determine what should be prioritized and how. It’s important to evaluate and prioritize which legacy applications to migrate and which to retire, refactor, or rehost, and which may require an architectural overhaul to fully utilize the cloud environment and achieve the intended benefits of migration. It’s not always about technical ease. While that can be important because of the cost of migration, if an app isn’t providing business value by being in the cloud, that indicates that others should be prioritized. The nature of legacy application modernization may make the relative cost-benefit analysis misleading or difficult to quantify. Carefully evaluate which applications will bring the most business value by being migrated. 

At larger companies, competing priorities can complicate the evaluation process. Usually the effort is being led as an enterprise-wide IT initiative, but each business unit might have their own IT with a dedicated view of just their applications and might not be equipped to answer the larger business value question. Another potential roadblock may arise if IT doesn’t fully appreciate the evolving needs of the business, which can be more easily achieved in the cloud. These might include greater scalability, higher availability, or additional security services which are built into the cloud. Technical value and business value are both important, so we always bring the business stakeholders into the conversation, rather than just the technical teams, so that all can evaluate and understand the relative costs and business benefits of the cloud migration

Business value as the crux of the evaluation criteria brings clarity to the situation. An application that functions for 10,000 users on-prem, but could be expanded to serve 100,000+ users on the cloud is a prime example of an opportunity for business growth that would not exist if the app remained on-prem. Identifying these nuggets of business value is a critical component of the prioritization formula. 


Ready to modernize your legacy application portfolio? 

Contact our experts to see how we can prioritize and roadmap your cloud migration and bring ROI and business value.

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