"Job shadows" offer young people a chance to investigate the world of work by spending time with adults in the community and experiencing the culture of the workplace. A job shadow gives a student a meaningful introduction to the world of work and provides a context for understanding the connection between school and careers. This guidebook was designed to help program coordinators and teachers design and implement job shadows for students. A job shadow is a worksite experience, typically 3 to 6 hours, during which a student spends time one-on-one with an employee observing daily activities and asking questions about the job and industry. Students complete written assignments before, during, and after the job shadow to help them understand and reflect on what they experience. When appropriate, students perform hands-on tasks at the work site. The guide offers suggestions to the program coordinator for creating the framework for job shadows--assessing students' interests, placing students at worksites, orienting partners, and handling logistical issues. It describes how teachers can structure learning during the job shadow and help students make a connection between what happens in school and at the workplace. The guide also includes fact sheets, classroom exercises, and sample forms. A glossary and index are included. The companion guidebook for students helps them structure their learning. It contains assignments that students complete before, during, and after the job shadow. (LMI)