It has long been known that generalist primary and early childhood teachers struggle with teaching music, due to a lack confidence and skills. This paper discusses some early findings of a phenomenological study which follows a twelve-month collaboration between a music specialist (the researcher) and a small group of early childhood educators in different pre-school settings. The multiple case study looks at this particular model of professional development through the eyes of the participant teachers, analysing their perceptions to identify how their general lack of music skills and confidence can be most effectively addressed. Through the data collected from the participants it can be shown that the general lack of confidence needs to be understood as a group of specific issues, referred to by the researcher as the "group of confidence". The different issues that make up this group of confidences can be successfully addressed through a mentoring collaboration that offers long term and consistent practical and moral support. In addition, the implications of the collaboration on both the participants and the researcher have become an important aspect of the study.