In the present paper, I discuss the internal conflict that accompanies the work of fellow pedagogical supervisors in teacher training institutes. Such internal conflict is manifested in the difficulty that pedagogical supervisors face in successfully integrating the subjective (the personal) and objective (the professional) dimensions of the work of pedagogical supervision. This difficulty, I argue, challenges the possibility of formulating ideological guidelines for the tutor-student relationship, and may ultimately negatively impact the quality of the teacher education process. Below I describe the complexity of the dilemma and its pedagogical implications. Subsequently, I propose a criterion for its resolution via Dewey's concept of "experience" which I have applied in the context of my work as a pedagogical supervisor in the Primary Education Program at Contradictory Components of Teacher Training.