There is a cultural mismatch between teachers and students in classrooms across the U.S. that, despite teachers' best intentions, too often leads to student harm. Mentors are uniquely positioned to interrupt conscious and unconscious bias that leads to inequitable practices but often have difficulty holding the necessary hard conversations. Among the reasons for this is socialized niceness, particularly in women, which prioritizes comfort and avoids conflict at all costs. Nina F. Weisling and Wendy Gardiner provide insights for recognizing, naming, and working through socialized niceness in mentoring to ensure all students have opportunities to learn in safe and rigorous classrooms.