This chapter examines the differences in facilitating a settlement-driven versus dialogue-driven mediation. It also examines the concept of introducing a humanistic approach to mediation and dialogue. The chapter presents the characteristics and qualities of an effective mediator in relation to the victim and offender, the facilitator’s responsibilities during preparation, the dialogue itself, and follow-up, including the significance of self-care. Nowhere else in the restorative justice process is the principle of respect and being non-judgmental more critical than in how the facilitator treats victim, offender, and other key stakeholders. Settlement-driven mediation is generally practiced within a conflict resolution context. In contrast, dialogue-driven mediation recognizes that most conflicts develop within a larger emotional and relational context characterized by powerful feelings of disrespect, betrayal, and abuse. Besides the governing values that define humanistic mediation, mediators must cultivate their emotional commitment to and connection with the highest principles they assign to the dialogue work.