For centuries informational reservoirs have been guarded and distributed by a select few. The diffusion of resources characteristic of the information age has made the accessibility of knowledge within the key stroking reach of many. This generalized value of accessibility has given validity to proverbial wisdom which avows that knowledge is power. Critical school leaders having internalized the principle that access to information is empowering to students. These leaders have begun to question the limitations of accessibility and skill development as it relates to historically marginalized students plugged into the information age. This chapter will explore the leadership techniques and strategies of high school administrators and faculty who embody the tenants of transformative philosophy as they prepare historical marginalized students to compete in the information age.