This is a book for anyone intrigued by the complexities of digital leadership that require a capability to constantly balance the routines of everyday business with the ability to innovate. Finding the appropriate mix between the dichotomy stability—flexibility has been a delicate task that few, if any, corporations have properly managed to overcome. Why is that? This conundrum becomes acute as businesses embark on digital transformations, an often-painful venture highlighting the deficiencies of traditional management styles but also agile methodologies. They deliver results that are far below initial expectations, provide half-baked digital solutions where potential commercial gains are poorly captured and leveraged, and, far too often, not even identified. Mismatches between technologies, the man-machine (dis)connect, or organizational dysfunctionality are typically identified as root causes, but beneath them lurks a more scathing problem: an inadequate leadership. This inadequacy rests on a lack of holistic insights backed by well-rounded skills and sets of knowledge that are required to understand all aspects of a digital transformation, as well as its participants from employees to customers. Thus, what is needed is a modern take of the Renaissance Man.