This paper presents the findings of a study focused on the experience of coaches when coaching millennial leaders (where millennials are those people born 1980-1999). Following a hermeneutic phenomenological approach using Interpretative Phenomenological Analysis (IPA), four coaches were interviewed using semi-structured interviews. Findings relate to the life stage of the coach compared to their millennial client, which resulted in coaches often playing the role of mentor; or to ‘the times we live in’, with millennial clients interacting with the world differently from their coaches, which affected coaches’ ways of working and work-life balance expectations.