Six steps to legacy system freedom: A practical roadmap

Your actionable guide to breaking free from outdated systems without breaking your organisation.

If you’re reading this, chances are you’re staring at a system that’s become more burden than blessing. Maybe it’s the finance platform that requires three workarounds to process a simple invoice, or the membership system that crashes every time you try to run an annual report. Whatever brought you here, you’re not alone—and more importantly, there’s a way forward.

During a recent webinar with leaders across the non-profit sector, my colleague Alan Perestrello and I shared six practical steps that can guide any organisation from legacy frustration to modern freedom. Having worked with dozens of organisations through this journey, I can tell you these steps work—but only if you approach them systematically and honestly.

Step 1: Start with a clear purpose

“Begin with purpose—and make sure it’s grounded in a solid business case that aligns with your mission and impact.”

This isn’t about creating a wish list of features or justifying the latest technology trend. It’s about honestly assessing what’s broken and why it matters to your mission.

What this looks like in practice:

Document specific pain points: Don’t just say “the system is slow”—quantify how much time staff waste daily on workarounds
Connect to strategic goals: How is your current system preventing you from serving your community better?
Build a compelling narrative: Your board and stakeholders need to understand not just the cost of change, but the cost of staying put
Set realistic expectations: Avoid the trap of promising transformational change that creates unrealistic expectations

Step 2: Engage people early and often

“Trustees and senior leaders must be in the loop from day one—without their buy-in, momentum stalls fast.”

Your system replacement will touch every part of your organisation, so every part of your organisation needs to be part of the journey from the beginning.

Your engagement strategy should include:

Senior leadership and trustees: They need regular updates and clear communication about progress and challenges
End users across departments: The people who use systems daily often have the best insights about what really needs fixing
Champions and influencers: Identify people who are naturally enthusiastic about change and can help bring others along
The sceptics: Don’t ignore resistance—engage with it constructively to understand legitimate concerns

Step 3: Clean house before you move

“Clean your data before it moves—bad data doesn’t improve with age or new systems.”

This step is about more than just data cleansing—it’s about taking a hard look at everything you’re carrying forward.

Your housekeeping checklist:

Data audit: Identify duplicates, outdated records, and information that’s no longer relevant
Process review: Which procedures exist because of system limitations rather than business needs?
Integration mapping: What needs to connect to what, and how will that work with your new system?
Archive strategy: What historical data do you actually need access to, and what can be stored separately?

Step 4: Simplify your processes

“Use this moment to challenge outdated workarounds—don’t let legacy limitations shape your future ways of working.”

Legacy systems often force organisations into convoluted workarounds that become “the way we’ve always done things.” Your system replacement is a chance to ask: what if we didn’t have to do it this way?

Questions to ask about each process:

What are we actually trying to achieve here?
Which steps exist because of system limitations?
How would we design this process if we were starting from scratch?
What would our users prefer, and what would serve them better?

Step 5: Test, test, test, test

“Relentless testing is where the real risk reduction happens—and it’s a step many underestimate.”

Testing isn’t glamorous, but it’s what separates successful implementations from expensive disasters.

Your testing strategy needs:

Scenario-based testing: Don’t just test features—test realistic workflows that mirror how you actually work
User acceptance testing: Get real users testing real processes with real data
Edge case testing: What happens when things go wrong? How does the system handle exceptions?
Integration testing: If systems need to talk to each other, test those conversations thoroughly
Load testing: Can the system handle your peak volumes without breaking?

Step 6: Train and enable your people

“Don’t just train—equip and empower champions who can drive adoption from within.”

Training isn’t just about showing people which buttons to click—it’s about helping them understand how the new system changes and improves their work.

Effective training includes:

Role-specific sessions: Different people need different training based on how they’ll use the system
Champion development: Train your internal advocates first so they can help support others
Ongoing support structures: Plan for questions and challenges that will arise after go-live
Documentation and resources: Create materials people can reference when they need help
Celebration of quick wins: Help people see the benefits early to build enthusiasm

Bringing it all together

These six steps aren’t just a checklist—they’re a mindset. Successful legacy system replacement requires treating technology change as organisational change, with all the complexity and opportunity that entails.

The organisations that succeed are those that approach this journey with patience, planning, and a commitment to bringing their people along. They understand that the goal isn’t just to replace old technology with new technology—it’s to build capability for ongoing adaptation and improvement.

Your next steps

If you’re feeling overwhelmed by the prospect of legacy system replacement, start small. You don’t need to tackle everything at once. Pick one step—perhaps documenting your current pain points or engaging a small group of stakeholders—and begin there.

The journey from legacy burden to modern freedom isn’t always easy, but it’s absolutely worth it. The organisations that take this step don’t just solve their immediate technology problems—they position themselves to thrive in an increasingly digital world.

Joyce Harmon is Head of Client Services at Hart Square, where she guides non-profit organisations through complex technology transformations. Hart Square’s technology-neutral approach ensures you get the right solution for your specific needs, with the support you need to make it successful.

Looking to break free from outdated systems?

Talk to Hart Square about how we’ve helped 250+ non-profits and membership organisations successfully deliver strategic, sustainable change—from business case to benefits realisation. Get in touch to take your first step or explore our expertise.