The purpose in writing this autoethnography was to describe, analyze and interpret one leader's experience in leading a group of online teachers. I specifically wanted to identify the characteristics of an online learning environment that triggered teachers to focus on management issues rather than instructional learning issues; that is what conditions should be in place to help teachers manage their online workload effectively to shift teacher discussions from management and metrics to student-centered learning; and finally how to ascertain what to do to better promote a leadership culture to inspire teachers in analyzing the teaching and learning process in the online classroom. This research was conducted as an autoethnographical exploration. Autoethnography was selected because it is specifically designed to study complex issues and promote self-reflection in daily praxis. It works well in situations where the researcher wants to better understand her role in connection with the culture under study. A socio-technical framework provided the theoretical lens for the study. It helped focus on the balance between the technical and social issues related to online learning. I looked specifically at how the teachers taught and promoted student growth in the context of this infused technology-based learning system and the extent to which the technical systems and infrastructure supported teachers' daily work. From my data and the analysis, three findings served as the basis for my recommendations for school leaders and my suggestions for further research: (a) online learning is highly social; (b) human interactions among teachers and students and deliberate support for students is important; and (c) existing policy drives the current management focus. Further research should be conducted to focus on the impact of state/district policy on student learning with a goal of creating performance-centered metrics of success. Policy decisions should drive student achievement rather than data management decisions such as the number of log-ins. There needs to be a clear and relevant process for the management of compliance issues, but state metrics for program success should first focus on measuring students' progress towards standard. [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.]