Mentorship is an established practice supporting learning in applied and experiential education. Although scholarship acknowledges that effective mentorship involves both process and relationship (Kwan & Lopez-Real, 2005), little is known about what allows for the development of positive and productive relationships between mentees and their mentors. This essay looks specifically at the mentorship of preservice teachers, and posits that at the heart of developing productive mentorship relationships is inquiry-based dialogue, an interpersonal method of fostering critical reflective dialogue through nurturing, thoughtful, inquisitive and non-hierarchical communication. The authors, who were partnered as mentor-mentee in a preservice teacher in-school immersion experience fifteen years ago, draw upon practitioner inquiry and oral history approaches to reflect upon their own mentor-mentee relationship. This article models the narrative nature of inquiry-based dialogue, while arguing that this form of dialogue can support strengthened mentor-mentee relationship through providing space for horizontal mutual engagement in core critical reflective questions about practice.