In this paper, Larkin and Gould’s (1999) activity theory methodology for defining work-related roles, and Burns’ (1963) analysis of organismic organizational form are merged into a model that describes associate and leadership roles and relationships in virtual organizations. The effects of a lack of a shared physical space and face-to-face social interaction, a continual need for learning and collaboration, and the temporalities that characterize roles and relationships in virtual organizations will be explored. This exploration will focus on the challenges that virtual workspace effects have created for two current leaders of virtual organizations. The acquisition and use of leadership power to meet these challenges will be discussed. Gifford and Enyedy’s (1999) activity theory, as well as interview data from six educators, will be used as a basis for drawing parallels between associate and leadership roles and relationships in virtual organizations and learner and instructor roles and relationships in virtual learning communities. These parallels will be extrapolated into a tentative model for pedagogical leadership in virtual learning environments.