Despite significant empirical work in the sport coaching domain, there remains a paucity of evidence to inform practice in high-performance sport coaching. As a result, there are gaps in our understanding regarding coaching expertise at different levels of athlete performance. A significantly underutilized approach in coaching research is Cognitive Task Analysis and it’s knowledge elicitation tools. Addressing these concerns, here we utilize applied Cognitive Task Analysis and a semi-structured interview protocol to elicit the cognitive challenges and use of knowledge by a group of N = 7 high-performance endurance sport coaches from a single national governing body. Analysis suggested prominent and ongoing challenges in day-to-day practice which, in turn require significant adaptive skill. In addition, results show how coaches used knowledge flexibly and conditionally to meet the demands of their role. A novel finding being the identification of the use of curriculum knowledge to mentally project the needs of athletes. The findings suggest opportunities for utilizing Cognitive Task Analysis to investigate the cognitive challenges of sport coaching and enhance coach development practice.