This article describes the pilot study of an informal assessment, the Student Transition Questionnaire (STQ). The STQ is a 38-item assessment designed to elicit student perspectives on transition-related topics. In this mixed-methods study, we piloted the STQ with 186 participants, and then conducted focus groups with various stakeholders. A factor analysis revealed STQ items grouped together around five factors. We found that the STQ was useful in distinguishing students’ perceptions of personal strengths and needs. Focus group participants considered the STQ to be user-friendly and helpful in promoting student engagement in transition planning; participants also identified several areas needing improvement. Implications for revising the STQ, its application in transition planning, and future research are discussed.