Teachers involved in a Master's level course in diversity participated in virtual, synchronous, anonymized discussions around issues of ethnic and racial diversity, gender, and stereotypes that could impact their students' participation in fields related to science, technology, engineering, and mathematics (STEM). Guided by theoretical frameworks from Social Cognitive Career Theory (SCCT) and Critical Race Theory (CRT), a convenience sample of 14 science and mathematics teachers participated in a series of virtual chats using open-ended questioning and facilitated by two university instructors. Using conversation and critical discourse analyses, three primary themes emerged: understanding of issues related to stereotypes, encouragement of females and minorities to pursue careers in STEM, and the place for diversity discussions in science and mathematics classrooms. The teachers felt burdened by curricular and administrative constraints that inhibit their ability to participate in thought-provoking critical conversations. The paper concludes with a discussion of ways teachers can assist in the STEM career identity development of their underrepresented females and students of color and calls for research that combines the key findings in SCCT and CRT to build confidence and capacity for teachers to effectively confront issues of racism, sexism, and stereotyping in science and mathematics classrooms.