Historically, the role of district central offices has been to efficiently execute policy and compliance demands around enrollment, funding, licensure, facilities, and academic standards with little attention to the processes and learning that is needed to promote high-quality instruction. This capstone examines the implications of organizing districts around the goal of execution rather than the goal of learning and high-quality instruction in Boston Public Schools. I examine the current system and use insights from District Learning Visits to inform how the district might reorganize around the central goals of supporting learning and high-quality instruction, particularly within the Division of Schools. The Boston Public Schools is a K-12 public school district serving 125 schools and approximately 49,000 students. It is the birthplace of public education in the United States and has a long legacy of leading the path in academic achievement. A key problem of practice for the Boston Public Schools is twofold: there is a culture of siloed work resulting in a lack of trust and coherence across district divisions, and the siloed work in each division is organized to execute rather than to learn. Each division executes in silos. There are few opportunities for district divisions to work interdependently with a focus on teaching and learning. The District Learning Visits strategic project was an effort to have central office leaders focus on teaching and learning and engage in deeper learning practices for themselves and those they supervise to improve student outcomes. This capstone focuses on the possibilities and limitations of shifting from organizing to execute to organizing to learn. Specifically, I use key characteristics of systems effectively organized to learn to assess the Boston Public Schools, such as the district's ability to provide process guidelines and tools that enable employees to collaborate in real-time, collect process data, and institutionalize reflection (Edmondson 2008). In addition, I offer the implications of this shift on multi-levels of the system beginning with my own leadership and growth, the Boston Public Schools, and the K-12 public schooling sector. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]