Over the course of the last several decades, K-12 educational systems have begun to adopt digital technologies to support teaching and learning. These tools have enabled the rise of online schools as well as fundamentally changing practices of school leadership. However little attention has been given to how instructional leadership is changed through the use of new media, or what leadership for learning might look like as more advanced versions of these tools are adopted in schools. This study looks towards the future of digitally mediated school leadership through an examination of leadership practices in the sophisticated player organizations in and around the massively multiplayer online game (MMO) "World of Warcraft" ("WoW"). By examining leadership practices in game, it seeks to understand how digital media structures leadership in playful learning organizations known as guilds, and the ways in which in-game leadership can inform current and future school leadership research and practice. This study was framed using theories of distributed cognition (Hutchins, 1995) and distributed leadership (Spillane, Halverson, & Diamond, 2001) as a means of defining what the actual tasks of leadership are in guilds and the communities of practice (Lave & Wenger, 1991) that surround them. Interviews were conducted with 14 different guild leaders from 11 unique organizations. Interview data was analyzed using Bolman and Deal's Four Frames in order to reflect meaningfully on parallels and differences between school and guild leadership. Findings include: the ways in which a data rich environment structures organizational leadership, the significance of interpersonal leadership in digitally mediated organizations, the ways in which both guilds and schools function as "nested communities of practice", and the fundamental differences between leadership of voluntary and involuntary populations. The study also includes a discussion of practical implications for contemporary school leaders, as well as a considering limitations of the work and possible avenues for future research. [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.]