Competency-based medical education (CBME) has produced large collections of data, which can provide valuable information about trainees and medical education systems. Many organizations continue to struggle with accessing, collecting, governing, analyzing, and visualizing their clinical and/or educational data. This hinders data sharing efforts within and across organizations, which are foundational in supporting system-wide improvements. Challenges to data sharing within medical education include variability in legislation, existing data policies, heterogeneity of data, inadequate data infrastructure, and various intended purposes or uses. In this eye opener, the authors describe four case studies to illustrate some of the aforementioned challenges and characterize the complexity of data sharing within medical education along two dimensions: organizational (single vs. multiple) and data type (clinical and/or educational). With the goal of better supporting data sharing initiatives, the authors introduce an action-oriented blueprint that includes a three-stage process (i.e., preparation, execution, and iteration) to highlight crucial aspects of data sharing. This evidence-informed model incorporates current best practices and aims to support data sharing initiatives within their own organizations and across multiple organizations. Finally, organizations can use this model to conceptually guide and track their progression throughout the data sharing process.