This article examines a unique pedagogical approach imbedded with collective learning experiences that engages students in a continuous cycle of mentorship. The research design is guided by two closely aligned methodologies, narrative inquiry and "testimonios." Narrative inquiry lends itself for the 'study of experiences as story'. A "testimonio" is an oral account, a verbal journey of the participant's life. "Testimonios/narratives" of students are drawn from multiple sources, including verbal reflection, journals, autoethnographies, mentor interviews, and personal interactions. As an instructor in the Urban School Leaders Collaborative, a program that leads to a Master of Education degree in educational leadership and principal certification, I am a facilitator of dialogue, a mentor and a mentee, learner and teacher. As a collective, we take part in deep collective critical reflection informed by a pedagogy of collective critical consciousness to fashion relationships of authenticity, equity, and reciprocity.