Today's school leaders are often stretched thin, juggling increasingly complex challenges with limited resources. This situation is exacerbated by veteran administrators leaving the profession, leaving less experienced principals and assistant principals to lead schools without substantial support. To address the evolving needs of school leaders, traditional professional development must be reimagined and tailored professional learning experiences must be provided. A culture of continuous improvement can be fostered by aligning these experiences with both individual educator needs and broader district goals. At Orange County Public Schools (OCPS) in Florida, the Leadership Development department, under the office of the Chief of Schools, created a customized experience for OCPS principals and assistant principals grounded in best practices and research. This article discusses the coaching program that was designed to support both new and experienced principals and assistant principals by providing mentorship and instructional support.