Despite extensive preparation in high-quality programs, novice teachers face a daily deluge of moments when their understandings about teaching are called into question in the living context of their new classrooms. These encounters often challenge new teachers' ideals about what teaching truly entails as well as their abilities to succeed in the profession. Once eager to begin teaching on their own, they find themselves working in isolation, wishing for opportunities to work through the challenges they now face within a network of like-minded colleagues, such as those offered by cohorts and university supervisors with whom their theories about the classroom coincide. In the face of these and other pressures, some decide that they might not be cut out for the job, when what they may really be lacking is the necessary support system to aid this transition. As a solution to this dilemma, the authors propose an increase in purposeful and meaningful dialogue. An effective mentor/protege relationship is essentially dialogical. Given that the mentor learns as the beginner learns, the mentor needs to take a dialogical stance to promote open conversations and investigation. Journals, blogs, observations, and subsequent debriefings help both the mentor and the beginner to learn much about teaching and learning.