Both physicians and attorneys complete highly rigorous academic regimens in order to prepare to practice in their respective fields. Rarely does the training in law school or medical school prepare them to manage either staff or departments. Leadership coaching for physicians and attorneys is a newer field, which is slowly beginning to gain traction in medical and legal fields. Through coaching, professionals gain insights into how they are viewed by their supervisor, peers, and direct reports and use this knowledge to formulate coaching goals, which are facilitated by an Executive Coach. Coaching approaches are based on theoretical knowledge, which provides coaches with a framework for their client work. This framework when balanced with the coach’s insights through observation, the use of assessments and instruments, and other data provides a comprehensive method for client intervention. This paper focuses on two case studies of coaching engagements, which were a part of the Organizational Consulting and Executive Coaching Concentration requirements: a Practicum with a retina surgeon, and an Executive Coaching Internship with a litigation department chair. The application of theory as well as a review of selected articles related to the training and coaching of physicians and attorneys is included to provide an understanding of the past, present, and future of coaching in these fields. This paper is written in first person to create a connection between the author and reader and offer an introspective viewpoint beyond the academic nature of the topics. The case studies, though not originally connected, offer a glimpse into two portraits of successful professionals striving to better understand both management and themselves.