North Carolina is one of several states that have begun to incorporate the components of the Framework for 21st Century Learning in its focus on school leadership development and support. A principal preparation program in rural eastern North Carolina initiated and designed webfolios for submission of evidences of internship learning experiences. Implementation and evaluation results from the pilot year 2007-08 indicated full implementation by both students and faculty. This paper will describe the process, perceptions, and lessons learned from students in the initial pilot group.