Our understanding and development of expertise in sport relies on the capture and assessment of performers in various performance environments, and the design of appropriate practice conditions. To truly understand sport expertise we must ensure that we accurately describe and measure performance under specific task constraints that effectively capture the functional responses of performers in representative situations (e.g., competition), before attempting to develop knowledge and expertise within this context (Araújo & Davids, 2009). The aims of this chapter are to discuss a range of issues and considerations in developing representative tasks in sport research and practice, and provide tangible examples, applied insights, and advice for researchers and practitioners.