While ‘soft skills’ are often viewed as add-ons in the digital journey, they are in fact critical to realizing the opportunities created by Industry 4.0 for the construction industry. This chapter focuses on a vital, but oft-neglected aspect of digitalization, namely Digital Leadership. By exploring understandings of digital leadership in the built environment, we show that digitalization demands that traditional views of leadership are broadened from an existing focus on senior figures in firms to embrace wider views of leadership across supply chains, projects and the industry as a whole. Skills in collaboration and a multi-cultural awareness are important components of this. This enhanced view of leadership is explored and practical examples of their application in firms, supply chains and projects in the construction industry are provided. The Teaching Case Methodology is introduced as a suitable pedagogical approach to address this growing skills gap in the industry and summarise data gather during recent sessions using this method. The data suggest some ‘dos and don’ts’ for digital leaders operating in the AEC industry and guidance on leading digitalization journeys across supply chains.