This chapter discusses the influence of leadership on emerging workplace design driven by technological developments. The chapter will also explore the monitoring, surveillance, and automation strategies utilised by business organisations to improve the effectiveness of their marketing initiatives. Despite the well-documented evidence for the effectiveness, efficiency, and sustainability of digital transformation of business organisations, it can have severe impacts on business stakeholders such as customers, employees, and society. We aim to focus on the luxury and fashion industry and propose approaches that leaders can utilise to implement and support digital transformation effectively.