This study uses critical race theory to examine interviews with university tutors, during which they reflect on teaching experiences with first-year students. These tutors are responsible for helping students to conceptualise racism as structural in the context of an introductory module in literary studies. The analysis maps the discourses tutors mobilised to assign meaning to the challenges and successes they experienced during their interactions with students. Analysing such interviews can contribute to critical race theory by illuminating how knowledge about racism is developed during tutor–student collaborations. The results elucidate how tutors attempt to make sense of an unforeseen measure of reluctance from students racialised as Black to discuss systemic racism and its impact on their lives. More specifically, the psychoanalytic concept mentalisation grounds my exploration of the various ways tutors engage different discourses to account for this reluctance. The same concept sheds light on tutors’ capacity to reflect on their own intersectional positionalities and its influence on students’ learning. The article concludes by stressing that mentalisation is less fruitful, analytically speaking, when it is used to accuse individuals of falling short of some desired criterion such as critical thinking. Instead, the real danger arises when people are unable to mobilise a wide range of discourses capable of driving sophisticated interpretations. Specific suggestions are made for addressing this danger.