This paper reports findings from an evaluation of a district-wide initiative deploying iPads to school administrators (principals) to improve workflow efficiencies and promote technology leadership self-efficacy. The findings indicate that iPad utilization not only facilitated administrative tasks (memos, calendars, etc.), but also improved specific complex administrator responsibilities such as teacher evaluations. School administrators perceived that their use of iPads improved their professional image, augmented their ability to lead in a technologically advanced workplace, and generated a significant return on the district's financial investment. Data, analysis, reflections, connections to teacher education, technology in schools, principal preparation and future research directions are presented.