The author investigates the symbolism of feminine and masculine energies in leadership through an exploration of the Arthurian legend of Parzival and the Holy Grail and Temple’s functional fluency model. Drawing on her experience as an educator, she reflects on a program she delivered for an all-male group in which she became curious about the impact of her presence as a female on their work together. She describes how exploring the “being in charge” role in the functional fluency model gave her a language with which to understand not only her impact on the participants but also their impact on her as they challenged each other’s frames of reference about leadership. She also reflects on how an understanding of feminine and masculine energies enables leaders to draw more fully on both and so experience more wholeness and a greater sense of authenticity in their roles.