Interest in cloud migration has steadily increased at the rate of 60% year-on-year since 2015. As more and more organizations move to cloud, they face challenges with lift and shift/forklift migrations. These include losses in application functionalities and performance degradation resulting in a higher TCO. It has slowly come to light that forklift migration is not the best-fit solution for a cloud movement and an application-down approach has to be considered for cloud transformations. This research discusses the need for organizations to take a holistic bi-directional view of both applications as well as infrastructure in order to achieve a business-oriented, risk-free & high velocity transformation.