Though coaching is a relatively young field, it is burgeoning in organizations. Designed to support individuals and organizations to implement their objectives (from job performance to team cohesion and strategic changes), the practice is gaining momentum given the volatility and complexity of our global and diverse environment. On its way to professionalization, it suffers from a gap between the advanced stage of the practice and the lagging academic discourse surrounding the field. This book intends to answer a call for increased connectivity between practice, theory, and research in support of a more professional, impactful, and ethical practice. We chose to address this gap by constituting a collection – derived from research we personally conducted – of 20 typical, yet complex, situations that practitioners face. Organized into ten chapters, these situations are positioned into the literature and commented on by world-class coaches, coaching researchers, educators, and program directors. The goal of this text is to create conditions to foster dialogue, questions, and solutions, between you, the reader, and us, the co-authors, as well as the “experts” who commented on the cases, together with your colleagues, supervisors, and/or classmates. Typical issues include ethical dilemmas, multiple agendas, and power dynamics, rooted in real situations experienced by coaches from different cultures and backgrounds.