Using the Gap Analysis problem-solving framework (Clark & Estes, 2008), this project examined collaboration around student achievement at the school site leadership level in the Pasadena Unified School District (PUSD). This project is one of three concurrent studies focused on collaboration around student achievement in the PUSD that include the teacher level conducted by Carruthers (2013) and the central office administrator level conducted by Llamas (2013). The primary purpose of this project was to identify the knowledge and skills, motivation, and organizational challenges that contribute to PUSD's gap in accomplishing its organizational goal for collaboration around student achievement from the perspective of the school site leadership. Mixed methods were used to collect survey data from 34 participants and interview data for four participants to identify and validate the knowledge and skills, motivation, and organization root causes that may contribute to the PUSD's school site administrator role in achieving the District's goal. Findings show that in general school site administrators are highly motivated and have the necessary knowledge and skills to meet the goals of the district but are impeded by issues related to resources specifically time for professional development, creation of job aids, assessments, and intentional communication to encourage collaboration across the district. Based on the findings, solutions are offered to address these challenges. This project, along with its concurrent studies, demonstrates how various stakeholders can systematically apply the Gap Analysis framework to address performance issues when implementing district-wide collaboration around student academic achievement. [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.]