This study investigated the impact of structured, five-to-seven-minute, one-to-one conversations every other day between the special educator and each student. Retrospective cohort analysis of six years of student grade point average data was used to measure the effect of the one-to-one conversations. Statistical analysis revealed a significant improvement (Cohen's effect +0.83) in academic outcomes in the one-to-one conversations cohort as compared to student outcomes prior to the course and versus the control cohort. These increases persisted in the after-transition period (Cohen's effect +0.99). Data from student feedback surveys revealed that students perceived one-to-one conversations as helpful and self-identified gains in self-reflection and independence. These results and their implications for future research and practice are described.