PurposeThe purpose of this paper is to explore mentoring experience through positioning theory lens. It discusses, specifically, the mentoring experience of beginning teachers and mentors in a school in Singapore.Design/methodology/approachThis study uses a case study approach. The data are collected mainly through interviews with beginning teachers and mentors.FindingsThe findings suggest that beginning teachers who had an emotionally assuring mentoring experience had mentors who positioned themselves as emotional providers. Those who had a professionally fulfilling mentoring experience had mentors who positioned themselves beyond the providers of emotional support. Beginning teachers who had a less satisfying experience had mentors who positioned themselves as physically and emotionally unavailable. Mentors who had a professionally frustrating mentoring experience had beginning teachers who challenged their positioning. Those who had a personally enjoyable and professionally satisfying mentoring experience positioned themselves as not averse to learning from beginning teachers.Practical implicationsThe findings suggest that schools may want to give more attention to mentor preparation, and it should not be a one‐off exercise. The findings also suggest that it may be a good idea to also consider a pre‐mentoring session for both mentors and beginning teachers before they embark on the mentoring proper.Originality/valueAlthough this study is at best a research in progress, it, however, signifies the first step towards initiating a dialogue in this aspect as there are hardly any studies that mentoring particularly in the context of Singapore. For the teaching profession in Singapore, this is especially a significant first step.