A conundrum of schools wanting to personalize and customize learning, to tailor it around individuals is juxtaposed against a lack of logistics and strategy in this discussion with Matt Yeager, Assistant Superintendent of Technology from Garland Independent School District in the Dallas, Texas area with 52,000 students.  Yeager introduces his theory of leadership and answers questions about what he means by tailored learning, missing logistics and his work in connectivity for schools and students. He provides additional valuable insights in strategic planning and how schools need to understand how technology will help them change structure and gain long-held desires to provide what learners and parents really want.