The study explores the educational potential embedded in the question-asking strategy as a key mentoring resource when used between an experienced teacher educator and a novice teacher for the professional development of both. The findings reveal that the process of a reflective dialog through asking questions led to deeper analysis by the mentor and novice and effected a change in the paradigm of the novice–mentor relationship. This self-study serves as an example of a teacher educator’s readiness to examine more closely her own mentoring style and its effects on the novice, and to better understand the contribution of a reflective dialog to the professional growth of both novice and mentor teacher.