In the last two decades there has been significant growth in the use of mentalization theory to conceptualize and organize the therapeutic practice of clinicians working with complex and multi-stressed families. In this paper we describe the supervisory use of the Family Cycle – a clinical activity designed to promote mentalizing in parents and children participating in an intensive home visiting program aimed at avoiding child/adolescent psychiatric hospitalization. We describe the Family Cycle in the supervisory context as a structure that facilitates fostering safety and regulation in the supervisory relationship, all in the service of mentalizing the experience of the families in therapy. We highlight barriers to working effectively with mentalization-based techniques and emphasize how supervisors can effectively model the mentalizing stance through interactions with clinicians. We end with a supervisory vignette illustrating concretely how one would go about applying this technique to supervision.