Educational leaders must be cognizant of the role of education in meeting the demands of society, equipping students with the necessary skills to function as successful citizens in their world. Antiquated, one way communication and direct instruction, the drill and practice behaviorist approach used by teachers and enhanced by such early technological innovations as television, film, and microcomputers (Whelan, 2004; Aslan & Reigeluth, 2011)were designed to accommodate the industrial age and assembly line worker, not the 21st century learner. Reading and writing are no longer the most demanded skills by employers; problem solving, team work and critical thinking skills are, expanding the definition of “literacy.” As Oblinger (2003) points out, the millennial learner believes “computers aren’t technology – it is an assumed part of life” (p. 39). Web 2.0/3.0 characterized by the ability of learners to not only consume information but to create, publish, and share information with a community of learners behooves educators to reconsider technological use and embrace constructivist pedagogical approaches to meet the needs of today’s learner. Thus, the challenge for educational leaders will be two-fold. First, to facilitate the necessary paradigm shift of 20th century- educated practitioners required for second order change – professional development and technical support, teacher retention and recruitment. Second, to consider and balance the cost effectiveness of technology plans – many web 2.0/3.0 applications are free but may lack appropriate technical support; open source resources can reduce costs but raise questions regarding authenticity; ubiquitous access will be a must, but the three w’s – wherever, whenever, and whatever, may pose risks to the safety and security of students and staff; environmental considerations – cost to recycle and destroy computers (Jensen, Taylor & Fisher, 2010).