Increasingly, principals are challenged to merge technology and instruction to achieve meaningful school reform. There are limited studies revealing the personal perspective of a principal who applied servant and transformational leadership to achieve school improvement by leveraging school-wide technology integration. The purpose of this qualitative autoethnography was to examine one principal leading a one-to-one laptop initiative to improve a high school. In this study, an autoethnographic layered account was used to examine my leadership as principal in a comprehensive, private high school serving a demographically diverse student body outside Chicago from 2003-2011. The method of autoethnography revealed the hidden thoughts, feelings, and actions applied to achieve technology-driven reform. The leadership framework for the study was the Interstate School Leaders Licensure Consortium (ISLLC) standards with expectations of setting the vision, collaborating, directing instruction, managing the learning environment, having ethics, and cultural responsiveness. Triangulation was achieved using analysis of documents and artifacts, stakeholder interviews, and a self-assessment. Documents analyzed included notes, emails, reports, and evaluations. Interview participants included the school's president, technology director, a math teacher, a science teacher, and administrative assistant. The 21st Century School Administrator Self-Assessment created by the National Association of Secondary School Principals (NASSP) provided self-reported skills in educational leadership, resolving complex problems, communication, and self-awareness. Findings revealed leadership experiences included communicating the vision, infusing change, empowering others, coddling resistant faculty, affirming success, and collaborating. The findings indicated that strong and principle-centered leadership was necessary in facilitating school-wide technology integration. School culture evolved from a general reluctance to change and disagreement of technology's value to a more collegial learning community that accepted ongoing changes in the school. The general learning experiences for students changed from passive to active. Recommendations include replicating this study with other principals implementing one-to-one laptop initiatives to create group case studies and developing a quantitative survey to investigate whether the results are generalizable. Implications indicate leading technology-driven reform is a culturally complex endeavor reliant on the skills of the leader and the results of this study can inspire further research about the increasingly important issue of leadership needed for technology-driven reform. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]