Legacy systems may have been reliable in the past, but over time, they become more of a liability than an asset. Whether it’s aging infrastructure, security concerns, or limited compatibility with modern tools, hanging onto outdated technology can slow innovation and hold your business back.
If you’re ready to modernize your IT systems, putting the right digital transformation strategy in place can help you reduce disruption and keep your business running during the transition. Here are five tips to help you make your legacy IT migration a success:
1. Review Your Current Environment
Before making any changes, document your existing IT landscape – including which systems are still in use, how they’re connected, and any risks they may pose.
Look out for:
- High maintenance or licensing costs
- Security gaps or lack of compliance
- Outdated software with limited support
- User experience and performance issues
This review will provide a clearer picture of what to prioritize in your system modernization efforts and where the biggest opportunities lie.

2. Define Digital Transformation Strategy
Developing a successful digital transformation strategy involves more than simply replacing one tool with another. Start by thinking through your goals, such as performance improvements or a smoother customer experience. It also helps to consider which environment will best fit your needs, whether that’s cloud-based, on-premises, or a hybrid approach.
Make sure your goals are specific and realistic. Define how your data will be moved and protected, what kind of access users will need, and what outcomes would make the migration a success.
3. Avoid Legacy IT Migration Pitfalls
One of the biggest mistakes businesses make during system modernization is underestimating the complexity of legacy systems. These platforms often contain custom code, outdated data formats, or undocumented processes, so it’s important to plan ahead.
This can also help you avoid pitfalls like:
- Migrating without a rollback or recovery plan
- Choosing solutions that aren’t compatible with your roadmap
- Failing to train teams on new tools before go-live
Ultimately, taking time upfront to properly plan, pilot, and train can prevent delays and disruptions later on.
4. Choose Scalable, Future-Proof Solutions
As you replace aging infrastructure, make sure to invest in platforms that will continue to support your team as your business grows. Look for flexible, cloud-ready solutions that are easy to scale, secure, and integrate with other tools – without the overhead of managing hardware or legacy software environments.
Ask questions about long-term support, regular updates, and whether the solution aligns with your roadmap. Choosing the right technology now can help you avoid another migration sooner than expected.

5. Bring Your People Into the Process
Technology changes can only go so far without buy-in from the people using it. Including your employees in early conversations can help you uncover what’s working, what isn’t, and what they need in a new system. Plus, their feedback can lead to better adoption once the migration is complete.
Make time for regular updates, involve key users in testing, and provide hands-on training and support. A strong rollout plan keeps your teams informed and confident throughout the transition.
Streamline Your System Modernization With OnDemand
Legacy IT migration doesn’t have to be overwhelming. At OnDemand, we work with businesses to design and implement modernization strategies that fit their needs. Our team brings vendor-neutral guidance, deep experience, and a personalized approach to help you move forward without added pressure or complexity.
Ready to replace your legacy systems with scalable, modern technology? Contact us today to get started with a tailored digital transformation strategy.