Background/Context The introduction of a racial equity policy provided an opportunity for one school district to examine its systems. The policy addressed structural inequity, as well as cultural literacy issues, internal personal biases, and other power dynamic differences in a historically impacted city. Researchers from a local research-practice policy partnered with the district Director of Equity to support the implementation of a racial equity policy that could be informed by data and research. Purpose/Objective The purpose of this study was to investigate if early warning indicators, specifically indicators of organizational readiness and a Director's leadership skills, could guide the implementation of a racial equity policy. Research Design The study explored using two instruments adapted from Adaptive Leadership to provide iterative feedback on the implementation of a new, challenging policy. Through development of an interview protocol that included potential leading indicators as well as qualitative prompts focused on readiness challenges and successes, the research team and Director met every three weeks to generate data and reflect on preliminary themes. Findings/Results The team found that the indicators of organizational readiness and leadership skill were helpful in informing on the current status and developing new ideas and scenarios to ease implementation of the policy. The qualitative data yielded themes highlighting critical tensions and focus areas essential for practitioners to consider when implementing a racial equity policy. Conclusions/Recommendations The primary implication of the study is that leaders and researchers need to focus on systems-level organizational work and the development of leadership skills. Leaders must anticipate district and school staff defaulting to technical rather than adaptive solutions, especially when addressing the goal of equity. While technical solutions are expedient and comfortable, they will not lead to true or continuous improvement. Moreover, the professional development work required is not singular or temporary, but rather embedded work, likely over many years. Also critical is team learning through authentic conversations making space for individuals’ lived experiences. A final step for developing systems-thinking is iteratively defining the metrics each office and school should be using to support this work formatively. As districts engage in such efforts, a focus on proximal, process-based measures will be more immediately helpful, particularly measures for staff, and not necessarily student data.