If you’ve ever been knee-deep in a spreadsheet that feels more like a house of cards than a data tool, you’re not alone. After years leading IT as a CIO, and now working closely with clients at TopBloc, I’ve seen organizations of all sizes wrestle with one of the most stubborn roadblocks in digital transformation: legacy systems and technical debt.
These systems may have carried us for decades, but today, they’re often more of a burden than backbone as they slow progress, increase risk, and drain resources. Think of legacy systems like an old flip phone: reliable in its time, but not exactly built for the world we live in now. Technical debt is the digital clutter that builds up over time—quick fixes, workarounds, or outdated integrations that were never meant to last but somehow became permanent. And when left unchecked, this debt makes change harder, slower, and costlier.
The Real-World Impact of Outdated Systems
I’ve worked with teams juggling a maze of disconnected spreadsheets—each one manually updated, riddled with complex formulas, and stored in siloed folders. It works, until it doesn’t. The time spent patching together these makeshift solutions is rarely counted, but it adds up fast. Worse still, these environments make it nearly impossible to scale, pivot, or innovate with confidence.
5 Ways to Tackle Legacy Systems and Technical Debt
1. Take stock and prioritize:
Start by identifying your mission-critical systems and the areas creating the most friction. Focus on high-impact upgrades that will make a visible difference in performance, security, or user experience.
2. Modernize bit by bit:
Digital transformation isn’t all or nothing. Ripping and replacing every system overnight is rarely realistic or necessary. A phased approach lets you modernize at a sustainable pace while minimizing disruption.
3. Embrace the cloud:
Cloud platforms offer scalability, flexibility, and better integration capabilities. By moving to Workday and other modern cloud solutions, organizations can reduce reliance on outdated infrastructure and simplify ongoing maintenance.
4. Teamwork makes the difference:
True transformation requires alignment between IT, operations, and business teams. When these groups collaborate from the start, roadblocks become smoother detours, not dead ends.
5. Invest in your people:
The best systems in the world can’t succeed without the right skills behind them. Empower your teams with training and tools to adapt and thrive in a modern digital environment.
Building for the Future
Digital transformation isn’t just about upgrading your tech stack. It’s about future-proofing your organization. By addressing legacy systems and technical debt head-on, you free up resources, reduce risk, and position your teams for long-term success.
At TopBloc, we specialize in guiding organizations through complex transformations with clarity, creativity, and care. Whether you’re migrating from legacy platforms or untangling a web of technical debt, we can help you build a roadmap that works for your goals and your people.
Ready to start clearing the clutter?
TopBloc can help modernize your systems and maximize the value of your Workday investment, reach out today to get started.
Brett Fahrner, VP of Customer Experience, Office of the CIO
Brett Fahrner, a veteran CIO with over 22 years of experience, has led IT teams across multiple industries, guiding leadership in building enterprise technology stacks that drive growth. He has implemented enterprise systems, overseen international M&A transactions, and managed technology through periods of rapid expansion. Brett’s expertise helps organizations navigate transformation with the right technology strategy.
