A global decline in students’ motivation and academic performance poses a serious threat to future competence supply, particularly in knowledge-driven economies such as Sweden. Despite higher education’s growing importance for economic and social mobility, the number of students pursuing such education continues to fall. This study employs a mixed-methods design using an explanatory sequential approach to explore how teachers’ leadership identity influences their aspirational engagement in shaping students’ beliefs and intentions to pursue higher education and future career opportunities. The results show that teachers who identify strongly with their leadership role exhibit a type of leadership that influences aspirational engagement with students. This, in turn, may promote students’ beliefs in their potential and intentions to pursue higher education through (1) aspirational engagement in individual dialogues with students, (2) aspirational engagement when introducing new subject areas in whole-class communication, and (3) aspirational engagement related to practical work experience (PRAO). This study demonstrates an understanding of the important potential of teachers’ contributions to elevate society’s future competence supply.