Many application development and delivery (AD&D) leaders acknowledge that digital business cannot exist on top of old, monolithic legacy applications, but most technology executives have been too conservative changing out back-end systems. Real digital transformation requires fast, sweeping modernization of old systems into new cloud-based systems that are agile, mobile, and able to deliver disruptive, real-time intelligence. We will introduce five signs that your current approach is not bold enough and five ways to turn your strategy around before it is too late.