As supervisors of preschool teachers, childcare center directors are well-situated to mentor their staff to pursue higher education. Telephone interviews with 78 directors examined their role as mentors in encouraging preschool teachers to take college classes. Educational mentoring was shown to be distinct from career mentoring. Logistic regressions showed that the director's educational mentoring of teachers and teachers' aides was associated with greater college attendance, whereas career mentoring was related to less attendance. Furthermore, the director's confidence staff members' ability to complete an Associate's degree promoted college enrollment. Finally, some directors appeared to be transformational leaders who created an education-friendly climate for their entire staffs. These findings suggest that the workplace is an under-researched, critical context for work-to-school mentoring. (Contains 1 table.)