As part of its ongoing engagement with community leadership, CSM hosted the 2019 San Mateo Leadership Program for its education day on December 7, 2018. Operated by the San Mateo Chamber of Commerce, the Leadership Program immerses local leaders in an intensive program of seminars on local government, business and services. The program also develops leadership skills and connects participants to professional networks in San Mateo County.

President Mike Claire, himself a graduate of the Leadership Program, hosted lunch, presented on community college education, and gave a campus tour for the class. Local school superintendents participated in a panel discussion on challenges faced in the schools, including Dr. Maggie MacIsaac, Burlingame City School District; Louann Carlomagno, Hillsborough City School District; Dr. Joan Rosas, San Mateo-Foster City Elementary School District; and Dr. Kevin Skelly, San Mateo Union High School District.