Developing and executing individualized retention plans for students. A career success survey is provided to a student, and the survey includes queries used to derive a student vulnerability index. A completed version of the career success survey with answers to the queries is received from the student, and an communication plan is assigned to the student based the completed career success survey (student vulnerability index). The dynamically assigned communication plan delivers messages to the student at periodic times in an effort to increase the likelihood of retaining the student or otherwise attempt to prevent the student from dropping out of an educational institution. The messages can include e-mail, mail, and telephone messages, and they can be sent at particular times during the student's enrollment at the educational institution. The content of the messages are personalized to the student based upon a number of criteria such as age, major, gender, identified needs, student vulnerability index, or any other criteria gathered by the system from the career success survey. The system also provides the basis of a student retention methodology for school administrators, faculty and staff by providing an environment for all concerted to better understand who the at risk students are, how to best help the at risk students, and a reporting system indicating improvement in student retention.