This capstone examines how a newly formed senior-level team worked together to complete a complex task, while driving towards a larger goal of becoming a learning organization. For the 2014-2015 academic year, central office leaders in the San Francisco Unified School District (SFUSD) worked to develop a new approach to the execution of their strategic plan, "Impact Learning. Impact Lives." In a continued attempt to decrease SFUSD's persistent achievement gap and to increase academic performance of "all" students, district leaders renewed their commitment to deeper levels of implementation for the strategic plan. During a series of senior-level team meetings in the spring of 2014, central office leaders realized that a number of district departments were inadvertently working at cross-purposes or duplicating efforts. Likely reinforced, in part, by previous and current SFUSD organizational systems and structures, district departments had become accustomed to working in silos, which, in turn, required limited system-level interdependence. Given the SFUSD senior leadership's desire to shift their organizational culture to one of learning together, this capstone explores the district's transition from silo driven work to cross-departmental teaming. The research section of this capstone outlines the principles of effective strategy execution and teaming. The analysis section describes the impact of the district's organizational culture on the application of these principles. The implications section identifies important components -- communication plans, cycles of inquiry, teacher and leader voice that are needed to ensure effective strategy execution in large, urban school systems. This capstone concludes with an acknowledgement of the challenges associated with organizational change and calls for continuous reexamination of strategy execution guided by research and reflection. [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.]