If war is an inherently human phenomenon, the discussion of the human aspects of war is as timeless as the discussion of war itself. One prudent starting point for any discussion on military issues is the philosophy of war described by the 19th-century theorist Carl Von Clausewitz. In Clausewitz, we have a life-long soldier explaining what it takes to reach the highest strata of the weapons profession; we would be wise to listen to what he has to say. Nevertheless, digitization is not just about technology. Only exposure to the best technology does not guarantee digital performance. More traditional companies must have the best mix of talent to drive to make a successful transition. Companies will blend internal expertise expected to be "digitally equipped" with chosen, externally attracted, "born-digital" talent from pure-play Web 4.0 or "Internet of Things" organizations, or from traditional companies more experienced in digital approaches. There is a big hurdle: highly experienced digital talent either capable of transforming or having the characteristics and skills to be technologically ready in the near future, is rare and in high demand. Leaders with "digital" or "internet" in their names are currently hot commodities. Compounding the problem: Leaders who are likely to succeed in leading a digital transition in a conventional company may have a markedly different profile from those who usually flourish in a pure-play, native-digital enterprise. Some research shows, born-to-digital executives may be more likely to rise through the expert ranks of pure-to-play work firms; they are often narrowly focused on one key area. On the other side, managers who excel in traditional companies appear to be largely based on their experience and abilities, including their ability to read people and inspire teams. As this analogy indicates, digital performance is not a' one-size-fits-all' skill proposition.