This chapter suggests that every coaching session—micro or macro—should be considered part of a holistic intervention contributing to the transformation of an organization’s cultural fabric. To achieve this, executive coaches need to be experienced in transitioning fluidly between micro and macro levels, and here it is suggested that the most effective can influence an organization’s culture by sensitizing leadership to the organizational dynamics; enabling a smooth transition from a micro to macro focus; reframing corporate culture; and importantly, via a case example, by creating a coaching culture. Such skilled group coaches have to engage with people throughout the organizational hierarchy, deduce rapidly team psychodynamics, and decide in the moment what really matters, being aware of the vicissitudes of leadership; i.e., they have to remain neutral, respond appropriately, and intervene judiciously. To be credible, they also must exhibit business acumen. Re-emphasizing that the ultimate aim is to create a coaching culture, the chapter then describes the objectives and benefits of coaching, and certain coaching methods—e.g., Socratic questioning—that can be used to achieve this. Finally, it is stressed that executive coaches should regularly assess and learn from previous initiatives, something only achievable via a true 360-degree evaluation.