Academic mentoring is increasingly being used by many universities as a tool to enhance the quality of research-led teaching, promote cross-faculty collaboration and encourage a mentoring culture and community. This article reports on a pilot project established to investigate the benefits of building flexibility into a structured academic mentoring program at the University of Sydney. Twenty-six academics from the Faculty of Business and Economics and the Faculty of Education and Social Work participated in the program. The mentors ranged in position from lecturer to professor and the mentees from associate lecturer to senior lecturer. Flexible arrangements were shown to be important in a variety of ways, from the pairing of mentor with mentee, to focussing on issues of work survival and life balance, research outcomes and career advancement. The project highlighted the lower number of male academics involved in formal mentoring, which merits further exploration. All participants reported positive outcomes, although refinement of the pairing process was recommended. A variety of unanticipated outcomes was reported by mentees.