This cross-case study explored leaders' systematic decision-making practices and persistence to become modern learning organizations. Given that this research is explanatory, the cross-case approach allowed for a comparison of the findings, identifying similarities and differences (Creswell, 2013) of how executive leaders from the different schools perceived the influence of the SB21 program had on their systemic decision making. The researcher utilized individual and paired interviews with 15 participants across three schools. The qualitative approach allowed the researcher to collect vast amounts of evidence through stories and events relayed through the participants (Merriam, 1998). These stories formed raw data the researcher used to make meaning by analyzing the data and then drawing conclusions from the findings. The findings in this study demonstrate school leaders can be trained to implement a systems approach to school reform. Therefore, the overall findings lead to the conclusion that all of the school leaders in this study exhibited persistence because they had available, strategies learned through the SB21 PD to overcome many factors that typically stall school reform. These strategies included: Engaging in targeted professional development, providing staff with appropriate support, utilizing a systems thinking approach to decision making, and using a combination of strategic, instructional, and transformational leadership styles. The study provides implications for practices executive leaders could utilize to move their schools to become modern learning organizations.