By Rajesh Jethwa, CTO at Digiterre, and co-author of Transform!: The 14 Behaviors Driving Successful Digital Transformation in the Age of Gen AI

Modern life runs on an intricate network of technologies so familiar we barely notice them. We see the polished surface of digital services, mobile apps and rapid delivery systems, yet beneath these innovations sits something surprisingly fragile. It is a vast ecosystem of legacy software, outdated infrastructure and deeply embedded organisational routines that were built for a different era. This hidden technology, a blend of code, machinery and human workaround, keeps the world functioning. Increasingly, however, it is showing signs of strain.

The more advanced society becomes, the more vulnerable it becomes to failures within this buried architecture. When modern systems falter, the effects can cascade instantly. The British Airways disruption in 2024 made this clear. A single technical fault led to widespread delays and cancellations, stranding thousands of travellers and exposing how dependent airline operations are on tightly meshed systems. Although air travel appears smooth from the outside, its core relies on a patchwork of old and new platforms. When just one piece collapses, everything stalls.

Transform, Behaviors Driving Digital Transformation

The global CrowdStrike outage offered an even more dramatic demonstration. A flawed update to widely used security software caused computers around the world to crash or lock into endless reboot cycles. Airports, hospitals and corporations all felt the impact. This incident revealed how deeply embedded certain tools have become and how a single error in one system can ripple across continents within minutes.

Another example is the UK Post Office Horizon scandal, where faults in an accounting system resulted in wrongful accusations against hundreds of postmasters. This was not only a technology failure but also a failure of change. An organisation that had become overly dependent on a single system assumed that any discrepancy must be human error. When technology becomes unquestionable, it gains authority that can override evidence and experience, with devastating consequences.

These events highlight a broader truth. Large scale digital transformation efforts often fail. Studies regularly suggest that between 60 and 70 per cent of such initiatives do not achieve their intended outcomes. Organisations underestimate the complexity of changing systems that underpin everyday operations. They invest in new software without addressing the outdated processes, cultural assumptions and decision making structures that surround it. Technology cannot succeed if it is layered on top of old thinking.

High stakes systems are difficult to change because they have become intertwined with human behaviour. Employees develop tacit knowledge that compensates for the shortcomings of old tools. This invisible layer of human patchwork allows outdated systems to survive far longer than they should. The paradox is that these systems seem stable precisely because people are constantly rescuing them.

But such arrangements cannot last. As expectations for speed, transparency and security grow, the legacy architecture becomes a bottleneck. Reinvention becomes essential for resilience.

The path forward begins with recognising that technology is only one part of the equation. True digital transformation requires rethinking how work flows, how decisions are made and how people collaborate. Organisations need clarity about the purpose their systems must serve today, not the assumptions they inherited from the past. Simplifying processes before upgrading tools reduces complexity and ensures that new technology is not forced to replicate outdated practice.

Reinvention also depends on small, continuous experiments rather than large, inflexible programmes. Pilot projects, prototypes and iterative learning build adaptability. They help organisations respond to uncertain...