Like never before technology is integrating into our existence. It has well and truly escaped from the confines of the desktop computer to permeate our environment both natural and artificial. As increasing numbers of humans interact with technology for many different purposes, on many different devices and in many different ways, design, in particular digital design, has become of paramount importance. Organizations are recognizing the importance of design and beginning to invest into design as a strategy to promote innovation and success in highly competitive global environments. Practitioners of technology are constantly searching for new technologies and new applications of technologies to make a more efficient and effective world. Not surprisingly then, attention is turning to design leadership not simply for organizational survival but also for fuelling ongoing technological innovation. The field of design leadership, particularly digital design leadership is, as one would expect, in its infancy, and although existing leadership in business literature provides some generic concepts for informing digital design leadership it is necessary to better understand leadership specifically as it applies to digital design. Borne of this need, the main aim of the present chapter is to make some contribution to the understanding of the capacities and capabilities of digital design leaders. To provide some background prior to discussing the capacities of effective digital design leaders, the idea of design is discussed, the role of the digital designer as used in the chapter is defined and some core ideas relating to leadership and design leadership are brought to the fore.