Given society's increasingly technology centric play and workplace environment, Massively Multiplayer Online Games (MMOs) can be an excellent sandbox to develop future leaders of teams, which are the lifeblood of any organization. MMOs like World of WarCraft provide rich immersive experiences that allow leaders and followers the ability to create highly complex ecosystems that can mimic some of the largest out of game organizations. In game they can potentially gain valuable insights, which can later be applied to the workplace. This study explores Leadership characteristics appearing in and out of game. A combination of identity theories and leadership characteristics provide a greater understanding of possible relationships that may be occurring between leaders and followers; and in and out of multiplayer video game environments. Using transformational leadership as a framework, 6 leaders were interviewed, and assessed with the Multifactor Leadership Questionnaire (MLQ). Also, their guild communities were examined for evidence of leadership behaviors. The results found relationships between a leader's in and out of game characteristics with values and contexts in the workplace between leader, community, and follower. These relationships create and shape the lived experiences of leaders providing them the insights to create connections between relevant contexts in game with their workplace environment. This study identifies leadership stories, that can been employed in the workplace for the benefit of the organization; and the use group play spaces as a place to practice leadership operations of a business. Through these narratives, leaders can better understand the values that shape their identity; the relevant contexts that enabled the appearance of leadership characteristics in and out of game; and an opportunity to connect with a community aligned to teach leaders how to be. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]