This chapter explores creativity in a high-performance sport coaching context, by sharing three composite vignettes each developed using an AI-assisted process adapted from Bakkum et al. (2024). Based on the authors’ professional work, these vignettes provide examples of creative coaches and how their creativity was promoted. The vignettes introduce Oliver Armstrong, a coach developer, and two coaches that he has supported: a volleyball coach who faced a crisis while preparing for the Olympic Games and a basketball coach who was seeking more innovative strategies to support player development. Following an iterative process of shared reflection, the authors identified a series of principles to guide the practice of creative coaches and those who support them. Emerging from reflections about our work through these vignettes, the discussion focuses on three principles of creative coaching (i.e., triggered episodes, contextual intelligence, and legitimate marginality) and two principles for supporting creative coaching (i.e., trusted guide and quality learning environment). Readers might consider using these vignettes to prompt reflective conversations and the principles to inform their practice.