Research has identified that parents are a key influence in the career planning process of adolescents. Despite this, limited research exists in regard to how schools and parents/guardians might connect in support of the career development process of youth. The purpose of this research was to explore what Saskatchewan parents/guardians do to support the career development process of their high school aged children, investigate what types of school-based supports parent/guardians deem most helpful in support of their children, and attempt to identify if and how parents/guardians and schools might connect in meaningful ways in support of the students’ career exploration process. The study targeted parents/guardians of Grade 10, 11, and 12 students within the province of Saskatchewan in the 2012-2013 school year. The initial survey instrument was an online questionnaire involving both quantitative and qualitative components. Follow-up telephone interviews were conducted to further explore various aspects stemming from the online results. Results identified specific school-based career supports deemed helpful, uncovered perceived gaps in career-related supports, identified the value of career conversations and communication, supported the notion of developing a common language for career development, and acknowledged the power of partnerships. Recommendations for both practice and research were presented in an effort to identify meaningful ways in which parents/guardians and schools may connect in order to help students develop the necessary career competencies to make informed decisions while creating and recreating their preferred futures.