Delivery Manager's Guide to Overcoming Legacy Software Migration Challenges - Part 1

With the application modernization services market size projected to reach USD 52.9 Billion by 2030 (1), it's clear that more companies are recognizing the importance of moving away from outdated solutions.

The main reason is that legacy systems often become a barrier to progress. What once supported daily operations can now slow down innovation, increase costs, and limit flexibility. Modernization is essential, but the process can be complex and full of challenges.

Piotr Rawski , our Delivery Manager at Grape Up , shares insights on overcoming key obstacles during legacy software migration. Part 1 of this two-part series will focus on dealing with knowledge gaps, aligning conflicting stakeholder interests, making future-proof decisions, and managing third-party dependencies.

With the right strategies and tools, including Generative AI, legacy software migration challenges can be effectively addressed, paving the way for a smooth transition.

Challenge #1: Limited knowledge of legacy systems

Over the years, legacy software tends to lose its subject matter experts, leaving gaps in knowledge. Documentation is often outdated or incomplete, making it difficult to fully understand how the system functions. This lack of information slows down migration efforts and can derail progress.

Our solution:

• We always start with a comprehensive discovery phase that includes interviews, daily operation observations, and reviewing any available documentation.
• We use Generative AI to analyze legacy code and incomplete documentation, quickly identifying key functions and dependencies. This ensures we fully understand the system and address any issues during the migration.

Challenge #2: Unclear target solution & conflicting priorities

Understanding the legacy system is just the first step - defining the new solution is another challenge altogether. In large organizations, multiple stakeholders often have competing visions for the replacement system, leading to confusion and conflicting priorities.

These competing interests can cause the product backlog to grow uncontrollably, making it harder to manage and prioritize tasks. This lack of focus makes decision-making slow and ineffective, putting the project at risk.

Our solution:

• We rely on the support of a single, decisive product leader empowered to align everyone around a shared vision and make key decisions quickly.
• For complex projects with shifting scopes, we focus on an agile, continuous discovery and delivery approach. This keeps the roadmap adaptable and allows teams to collaborate in real-time.
• To manage conflicting demands and maintain focus, we use MVP/MDP approach and prioritization strategies to make sure we deliver the most critical features first.

Challenge #3: Making strategic decisions for the future

Migrating legacy systems provides the chance to modernize, but if the new architecture isn’t designed for scalability and future growth, you risk creating technical debt that requires further migrations down the line.

Our solution:

• We start by conducting a thorough SWOT analysis, which helps evaluate the pros and cons of different technology options and infrastructural choices.
• We also use Architectural Decision Records (ADRs) to document key choices. This ensures that future teams understand and respect decisions made during migration, preventing unnecessary changes.

Challenge #4: Managing third-party dependencies

Legacy systems often rely on a web of third-party services that might not integrate smoothly with the new solution. Some vendors may be slow to adapt to required changes, and hidden dependencies can crop up late in the process, causing delays.

Our solution:

• Before starting a migration, we establish clear governance over partnerships with third-party vendors, ensuring that expectations, timelines, and responsibilities are aligned.
• Generative AI helps us identify and analyze hidden dependencies early, reducing the chance of unwelcome surprises down the road.

Migrating legacy systems is challenging, but your organization can move forward confidently by addressing these key issues. In Part 2 of the article, we’ll explore further challenges, including resource management, budgets, and how to execute a smooth data migration and rollout strategy.

Let's discuss challenges to legacy migration and modernization

Do you have a legacy system that’s holding you back?

Have you encountered similar challenges in trying to migrate or modernize it?

If you're curious about how we solve software modernization issues, talk to us. At Grape Up , we’re ready to help you upgrade your systems with minimal disruption and for long-lasting results.

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Source:

1) https://www.globenewswire.com/news-release/2023/11/22/2784824/0/en/Application-Modernization-Services-Market-to-Hit-USD-52-9-Billion-by-2030-Research-by-SNS-Insider.html