Difficult conversations about "isms", power, privilege, and oppression are an essential part of social work education, and they present unique challenges for students and faculty. The current study examined students' and faculty's perceptions of the safety of the classroom and the competence of the faculty in facilitating difficult conversations at a graduate school of social work in New York City. Student and faculty versions of a survey were distributed to both groups. Results indicated students rated the experience of having difficult conversations at the school significantly more negatively than the faculty did. The majority of respondents expressed the need for courses and training to be more fluent in having difficult conversations. Future directions are discussed based on the findings.