The purpose of this study was to evaluate the leadership styles and the extent to which central office administrators are using technology and compare this to the districts' practices regarding the integration of technology. The intent was to find if there was a correlation that existed between a digitally advanced administrator at the central office level with digital transformation practices in the district. Additionally, the goal was to create a profile or model of an effective digital leader from the research and data. This study is a mixed method of qualitative and quantitative research designed to address and research pertinent issues in educational technology leadership. These data were collected through an adapted and modified version of the CoSN (Consortium for School Networking) Digital Leadership Team Assessment and Empowered Superintendent Self-Assessment tools distributed to central office administrators in Nassau and Suffolk County school districts on Long Island, New York. The 82 participants of the study were superintendents, assistant superintendents and other central office administrators across Long Island. The data analysis was followed by one-to-one interviews of four superintendents chosen with high technology use based upon their responses to the assessment tool. Additionally, the researcher addressed the definition of leadership based upon literature reviews and international technology standards for administrators as set forth by ISTE (International Society of Technology in Education). The types of leadership include: transformational, innovative digital, and future ready and address how the culture of the organization is affected by these types of leaders. A strong and significant correlation .86 was found between leadership and district practices from this study. Implications such as changing interview and hiring, practices for administrators to include more than just interview questions is relevant and needs to be addressed for the technology advancement in public education. A recommendation for future research is to conduct a comparative study of central office administrators with building level administrators to see if there is a difference in practice and usage. Another recommendation is to do a case study of a highly effective digitally advanced and recognized district and discover what leads to their success. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]