This paper argues that Liz Lerman's and Larry Lavender's approaches to mentoring student choreographers denote a shift in the philosophy of choreographic mentorship in higher education, because they reflect current concerns in critical pedagogy. My particular interest is in the relationship established between student artist and educator when a philosophy of critical pedagogy is infused in the choreography classroom. Lerman's and Lavender's philosophies create space for students to explore a wide range of material, they allow for more agency, power, and risk taking in the students' choreographic practice, and they also allow for a reciprocal student to mentor relationship. By enacting simulated conversation with these mentors in this essay, representing their voices and choreographic principles, I locate and analyze the elements of choreography craft and process that they value and those that they omit or reject. New insights into the philosophies of these important figures are gleaned as I play their parts, interacting with them as choreographer to mentor. The staged conversations are then reanalyzed through a lens of critical pedagogy for a closer investigation of what future mentorship could look like. This paper reinvigorates choreographic mentorship, interweaving narrativity, choreographic analysis, and pedagogical analysis in experimental ways.