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The authors develop a ‘transactional’ account of mentoring, based on the theory of communication in John Dewey’s mature works. This account addresses two well-documented problems in mentoring communication: mentors’ frequently listen insufficiently and possess inadequate grasp of mentees’ situations and goals, particularly those of mentees from underrepresented groups; mentors’ motivations for entering mentoring relationships often remain unexamined, leaving room for hidden agendas leading to mentee harm. Conceiving mentoring communication as ‘transactional’ significantly reframes the standard interactional account as a blurring of identity boundaries between participants leading to subsequent revitalization of both. A ‘transactional’ account also involves genuine mutuality, reciprocity and equality of status within the mentoring communication situation, emerging from openness, vulnerability and creative imagination depended upon by both partners.