A symbolic compilation of stories centered in a variety of organizational settings is presented. Through fictional characters and organizations, the narrative illustrates a variety of models, theories, and techniques that coaches might utilize when working with clients. This series of professional parables brings to life an assortment of executive coaching situations and leadership dilemmas where individuals are challenged to address issues, alter approaches, and overcome obstacles. While all persons, places, and activities are imaginary, the approaches and recommendations represent real-world descriptions. Each of the five stories told offers opportunities for both coaches and clients to strengthen their communication skills, to connect with each other by establishing common ground, and to contribute to their respective roles in the workplace as well as the world. This collection of models in action is a blueprint for building relationships, a framework for moving forward, a catalyst for creating change, and a template for taking the next steps.