Montessori middle schools can be immensely successful and highly beneficial to students. Traditional schools notice differences in students who come from Montessori backgrounds; they find them to be adaptable self-starters who often take on leadership roles. Prestigious high schools seek to recruit Montessori middle school graduates. As more parents seek alternative educational plans for the teen years, often deemed the most difficult, more Montessori programs, both public and private, appropriately strive to meet this need. The value of adolescent programs that provide a holistic, substantive, and developmentally based experience for their students is becoming more recognized. In this article, the author provides a list of guidelines to consider when developing a successful Montessori program for middle school students.