Key Takeaways
Legacy software is tolerated because, let’s face it, it works, and works well. But that’s no longer good enough. Nowadays, it limits an organisation’s strategic options. Legacy software can slow down, or make strategic plans more expensive or complicated than they need to be.
Whilst legacy software is considered stable, the real risk isn’t system uptime – it’s the software engineers who understand your legacy systems retiring. It’s the core logic that frequently lives in undocumented code written decades ago. It’s the regulatory, security, and integration demands which are increasing.
Why CEOs Should Modernize
Many manufacturing and financial services companies still use software built decades ago. This software is stable and reliable but it isn’t flexible. There are many reasons why CEOs should modernize their software and NOW is the right time to do it.
If your core systems still run on COBOL, RPG, Visual Basic 6 or SAS, this isn’t a problem for your IT team. They’re used to it and can work with it. Instead, it‘s a leadership decision. One that sits with the CEO.
Legacy software has been tolerated because it “works.” It processes transactions. It keeps the lights on. There’s been no disastrous failures as yet. But that’s no longer good enough.
1. Stable isn’t the same as safe
Legacy systems are often described as stable. However, this stability is becoming more and more fragile. The real risk isn’t system uptime – it’s the software engineers who understand your legacy systems retiring. It’s the core logic that frequently lives in undocumented code written decades ago. It’s the regulatory, security, and integration demands which are increasing.
When something does go wrong, the issue isn’t whether the system can be fixed. It’s how long it takes, how much it costs, who is affected, and, importantly, who notices. You don’t want your customers to be the first to notice.
2. Legacy technology limits strategic options
Most CEOs have clear growth ambitions:
- Increase turnover and profit
- Launch new products and services
- Improve response to customer demand
Legacy systems don’t necessarily block these. But they can slow them down, or make them more expensive or complicated than they need to be. Over time, decisions might be shaped by what’s technically possible rather than what makes commercial sense.
While it takes time and it might be too costly for you, but it’s not for your competitors who have already modernized.

3. The real cost shows up where you least expect it
Legacy platforms often look cost-effective because you’ve had them so long they’ve become great value for money. That’s misleading. The real costs show up as:
- Long delivery timelines
- Manual workarounds
- High dependency on scarce software skills
These costs grow as the business grows. What once felt manageable affects margins and momentum. A hidden cost is also things you just can’t do technically, because they are not supported by your platform.
4. Reputation, talent, and future proofing matter
Technology choices send signals. High-quality talent want to work in environments that invest in the future. High caliber software engineers want to work in environments that use modern software where they can learn and grow. Partners and investors look for organizations that can execute change quickly if needed.
Persistently deferring modernization sends a message:
- We’re prioritizing short-term comfort over long-term capability
- We’re carrying avoidable risk
- We’re reactive rather than proactive
That’s not how CEOs want to be positioned.
5. Modernisation is no longer an all-or-nothing gamble
One of the biggest misconceptions is that modernization requires a risky, disruptive “big bang” programme. That’s not the case.
Modern approaches allow companies to:
- Modernize in phases
- Keep systems running throughout
- Test frequently
- Deliver measurable results at each stage
- Reduce dependency on obsolete skills
The greater risk now lies in standing still.

6. AI integration
A fairly new reason why CEOs should modernize is that old legacy systems cannot make the most of new AI technologies because they can’t be integrated easily.
7. Legacy software can work against you
Legacy software either enables your strategy or quietly works against it. For CEOs, modernization is not about technology for its own sake. It’s about:
- Managing operational and regulatory risk
- Protecting growth plans
- Ensuring your organization can adapt
- Leaving the business stronger than you found it
- Reacting quickly to external threats and opportunities
The decision isn’t whether modernization will be needed. It’s whether it’s done on your terms in an organized way, or later under pressure – frantically.
That choice sits at the top.
AI integration image created and content researched using CoPilot.