There’s a common belief in tech: to stay relevant, you must constantly chase the newest frameworks, languages, and tools. But what if the opposite skill — mastering outdated systems — is equally, or even more, valuable?
Former Meta tech lead Alex Chiou recently posted that “reading terrible legacy code is a much more important skill than writing fresh good code.” And he’s right. Unless you join a brand-new startup, chances are you’ll spend much of your career working in someone else’s codebase — and often, in systems that have been around for decades.
Legacy Tech Is Everywhere
The idea that most companies have modernized their entire stack is a myth. From banking systems running on COBOL, to manufacturing software tied to proprietary APIs, to government agencies still operating on Windows NT, legacy systems run a massive share of the world’s critical infrastructure.
Even in big tech, the deeper you go, the messier it gets. Large, successful companies have code touched by dozens (sometimes hundreds) of developers over the years. The result? Layers of spaghetti logic, half-documented business rules, and design decisions made under constraints that no longer exist.
At the end of the day, all code ages. What feels modern today will be tomorrow’s legacy — and the next developer will face the same challenge of reading, understanding, and making sense of it.
Why Old-School Skills Still Matter
Being able to read, understand, and work within old systems is more than just a survival skill — it’s a competitive advantage. It means you can:
- Keep mission-critical systems running while the business explores modernization.
- Troubleshoot issues when documentation is missing or wrong.
- Translate undocumented logic into maintainable, updated processes.
- Evaluate replacements with a deep understanding of what’s being replaced.
In other words, legacy fluency buys companies time — and time is often the most valuable commodity during transformation. Modernization projects rarely happen overnight; they can take months or even years to complete. During that period, the organization still needs its existing systems to operate reliably. If those systems go down, business operations stall, customers are impacted, and transformation goals are delayed.
Being able to keep those legacy systems running smoothly while new solutions are built is like having a safety net. It gives the company breathing room to plan migrations carefully, test changes thoroughly, and avoid risky “big bang” cutovers that could jeopardize both revenue and reputation.
The Mix That Wins: Old and New
Of course, you can’t build the future on legacy knowledge alone. The most effective teams combine two kinds of talent:
- Maintenance Talent (the old folks) — people who’ve been through the toughest systems, know the quirks and history of the code, and can repair or adapt it without breaking what’s already working.
- Transformation Talent (the new folks) — professionals who bring modern frameworks, fresh perspectives, and forward-looking practices that make systems more maintainable, scalable, and aligned with current business needs.
When these two work together, organizations get the best of both worlds: stability and innovation. Maintenance Talent ensures the systems that keep the business running don’t collapse during change, while Transformation Talent paves the way for scalable, maintainable solutions. The challenge is getting both groups to share knowledge and work toward the same outcome.
It’s worth noting that the need for talent in emerging technologies often gets more media attention — and for good reason, given the opportunity cost of not adopting new tools that can drive innovation or reduce costs. But in the shadow of that spotlight, the role of developers who understand and maintain legacy systems is frequently underestimated. These are the people who keep the invisible machinery of operations running day after day.
As the old IT adage goes: “The work is done well when nobody notices.”
The Opportunity Cost Question
Some argue that keeping legacy skills sharp takes time away from learning high-ROI “buzzword” technologies. That’s true — but it’s also a question of balance. Legacy maintainers might not create flashy demos, but without them, the business might not function long enough to experiment with the next big thing.
The Long Game
Legacy systems will be with us for years. Many companies still run a significant part of their operations on them — and will likely continue to do so for quite some time. Modernization is a delicate process that requires time, coordination, and careful planning.
During that transition, it’s critical that existing systems continue to operate without disruption. The teams who still depend on them — and the processes that rely on the data they produce — can’t afford downtime, bottlenecks, or unreliable outputs. This is where deep legacy knowledge becomes a strategic asset, ensuring stability while transformation efforts move forward.
The paradox is that you need experts in the old stack to dismantle it— and when done right, those same experts transition to the new stack along with the systems.
At Inclusion Cloud, we help you find that sweet spot for your team — combining the right mix of Maintenance Talent and Transformation Talent. Whether you need individual experts to strengthen your current team or Agile Pods and cross-functional teams ready to accelerate your initiatives. Contact us!
Some strategic insights for legacy management
How can investing in legacy system expertise actually impact our business risk profile?
Legacy system expertise directly reduces operational and strategic risk. Organizations without skilled legacy teams face higher probabilities of downtime, errors in critical workflows, and costly delays during modernization projects. For example, an undocumented COBOL process in a banking system can halt transactions if no one understands it. In this case, legacy experts act as a safety net, as they can quickly troubleshoot issues, implement temporary fixes, or translate old logic into modern processes without jeopardizing operations.
But, beyond minimizing technical risks, they also reduce financial and reputational risk, ensuring that critical services remain reliable while the company pursues transformation initiatives. In essence, investing in legacy fluency strengthens both operational resilience and the company’s ability to innovate safely.
What is the ROI of balancing maintenance with transformation talent?
ROI comes from avoiding costly disruptions and accelerating modernization. Maintenance talent ensures that existing systems continue to run smoothly, preventing emergency fixes or downtime that could cost thousands—or millions—in lost revenue. Transformation talent, on the other hand, drives innovation, scalability, and efficiency in new systems.
By integrating the two, organizations reduce project delays, avoid repeated work, and maintain business continuity during transitions. For instance, when migrating a legacy ERP, maintenance experts can preemptively flag high-risk processes, while transformation teams implement the upgrade efficiently. This combination reduces indirect costs associated with errors, accelerates adoption, and ensures the investment in modernization delivers measurable returns rather than being stalled by preventable incidents.
How measuring the effectiveness of legacy skills within a modern IT team?
Legacy expertise can—and should—be quantified through operational metrics and project outcomes. Common measures include mean time to repair (MTTR) for legacy system incidents, frequency of unexpected downtime, accuracy of translating legacy logic into modern workflows, and the speed at which migration milestones are reached without major errors.
Another key indicator is knowledge transfer effectiveness: how well legacy experts document processes, mentor newer team members, or ensure that critical understanding doesn’t leave with retiring staff. By tracking these metrics, executives can see that legacy skills are not just “nice to have”—they directly influence reliability, project efficiency, and risk reduction.
Are there specific industries or business models where legacy expertise is more critical?
Yes, industries with high regulatory oversight, long product lifecycles, or mission-critical infrastructure benefit most from legacy expertise. Banking, insurance, healthcare, government, and utilities often run essential operations on decades-old software, where downtime can trigger regulatory penalties, financial loss, or reputational damage.
For example, a hospital relying on legacy patient management systems cannot afford system outages without affecting patient care. Organizations in these sectors gain a competitive advantage by maintaining staff who understand these systems—they can modernize at a measured pace while protecting core operations, ensuring compliance, and preserving trust among customers and stakeholders.
How to institutionalize legacy knowledge before it leaves the organization?
Capturing legacy knowledge requires a structured, multi-pronged approach to ensure critical expertise doesn’t walk out the door. Executives can implement the following strategies:
- Structured Documentation: Create detailed, version-controlled repositories of legacy code, process logic, and business rules. Include code annotations, flow diagrams, and decision rationale to make knowledge accessible to new team members.
- Mentorship and Knowledge Transfer: Pair legacy experts with transformation or newer team members on active projects. Encourage shadowing, pair programming, and hands-on learning so tacit knowledge—like quirks and workarounds—is transferred effectively.
- Internal Knowledge Bases: Develop wikis or intranet portals that store legacy system procedures, troubleshooting guides, and FAQs. This centralizes information and reduces dependency on individual experts.
- Automated Code Analysis: Use tools that can scan legacy code for patterns, dependencies, and undocumented logic. This not only documents hidden workflows but also helps assess modernization risks.
- Cross-Functional Project Teams: Embed legacy experts in modernization initiatives to ensure legacy knowledge informs planning and execution. This encourages real-time knowledge sharing and reduces errors during system migration.
- Succession Planning: Identify critical legacy roles and plan for gradual handoffs. Incentivize knowledge transfer as part of performance objectives to ensure continuity.
- Regular Review and Updates: Legacy knowledge isn’t static—review and update documentation periodically to reflect changes, fixes, or new insights gained from operational experience.
By combining these strategies, organizations can preserve legacy expertise as a sustainable asset, ensuring smooth modernization while maintaining operational stability.