Supervision provides benefits for school counsellors and career counsellors such as support, an opportunity to gain new ideas and strategies, and personal and professional development. Despite this, studies have also shown that school counsellors perceive that the amount of time they participate in supervision is inadequate. In career counselling, there is little evidence that supervision has even been established as a mainstream professional practice. The reasons for this curious situation, whereby little time is spent on a potentially beneficial activity, are uncertain. The present study investigated the supervisory experiences of a group of school counsellors and career counsellors for a six month period following their completion of an intensive supervision training program. Participants recorded their supervisory experiences in a structured diary. Even though the participants were well informed about supervision, the findings of the present study are consistent with those of previous studies. This history of repeatedly similar findings suggests that it may be timely to ask some fundamental questions about supervision in these two professions. Such questions in turn suggest possible new research directions.