Continuing education advances society. For every student, our educational system should provide a seamless transition from one level to the next until a degree or certificate is earned that reflects a mastery of skills needed to secure employment. This helps prepare each individual for a successful life after exiting the educational system and greatly benefit our society. Today, however, many students graduating from high schools are not ready for a postsecondary education. Transitioning students from high school to college is a complex process that requires many different approaches. Students making this transition are finding it more difficult to enter and succeed at a higher level of education because of the complexity of this process. Preparing students for postsecondary options is critical for every student. Students from low-income families and some ethnic and racial minority groups are most dependent on the ability of their high school to prepare them properly for college success (Conley, 2010). In what ways can schools better prepare students for postsecondary success? This study focuses on the creation of a Postsecondary Readiness Guidebook (PRG) which provides a comprehensive approach to help educational leaders prepare students for postsecondary success. The guidebook uses a problem-based learning design and follows the research and development process. The guidebook was field tested by educational leaders in a K-12 public school though a workshop using a qualitative methodology. During the field-testing of the guidebook, data were collected through assessments, interviews with educators, and questionnaires completed by educational leaders at the school. Data were analyzed using inductive coding, facesheet coding, enumeration, and typology. The findings of the study reveal that using a guidebook with a comprehensive approach to postsecondary preparedness can help school leaders prepare students for postsecondary success. Educational leaders in the school collectively focused on best practices and programs aimed at preparing students for postsecondary options through the use and interaction of the PRG. The guidebook gave them a compass for which to navigate the complex process of preparing students for postsecondary success.