Coaching creatively is the ability to develop (new and useful) training, competitive, and relational outcomes driven by a desire to explore and innovate coaching practices. The aim of this chapter is to explore how coaches can learn to coach creatively. We introduce two complementary pedagogical approaches, social learning theory (SLT) and design thinking (DT), as potential pathways for reimagining coach education. To begin we provide a brief overview of the literature on coach learning and development, emphasizing opportunities through participation learning situations (i.e., coaches learn through interacting with others). We argue that the reflective, collaborative, and experiential mechanisms embedded in these situations can foster more creative and innovative coaching. Next, we examine each pedagogical approach independently before highlighting their conceptual overlaps through a fictional case study (based on a set of real events) about how a coach developer named Andy enacted coaching creatively in practice. To conclude, we offer practical recommendations tailored to those working to build exceptional learning environments and guide the development of creative coaches. This chapter is especially beneficial for sport administrators, coaching associations, and coach developers who can nurture creative coaching from the grassroots to the professional stage.