The advent of digital technologies has opened up an online space that is transforming the architecture of every aspect of our social life. The social forces unleashed by human interactions in this online space are upsetting the equilibrium of multiple aspects of our pre-existing order, not the least of which is the way in which leadership is envisioned and practiced. Notions such as “smart mobs,” or real-life “leaderless movements” such as the various “Occupy” movements around the world, highlight the effective agency of grassroots networks that are enabled by an ever-growing array of digital and wireless communication technologies. These technologically driven social experiments cast into doubt familiar notions of and approaches to leadership that are hierarchical, top down, command driven or control oriented, or that rely on the charismatic authority of a few. Meanwhile, a new set of leadership dynamics that are participatory, collaborative, networked, and that allow for a diffusion of power at the grassroots, are beginning to emerge. These changing expressions of leadership call for a questioning of what leadership means in the digital age: what are some commonly held notions of leadership? To what extent are these familiar notions challenged by the advent of the digital age? What kind of ideal digital social space do we want to build? What kind of leaders does it need? What skills and visions would such a leader need to have?