Financial Services (FS) firms consistently have systems which are less reliable and of poorer quality than other industries[1]. Many of us as customers of banks and other FS providers have experienced the frustration of systems and processes that fall short of our expectations, sometime dramatically so. And there have been many examples of major banking and payment system failures in the news over the years which cause huge frustration and hardship for people and companies. Clearly this is not a great starting point for banks that are trying to digitally transform their operations and services. But why is this, and what does it tell us about how to prepare for a Digital Transformation?