This qualitative study explored the experiences of a sample of secondary school counselors who facilitate groups. Specifically, 18 diverse secondary school counselors were interviewed regarding how they conceptualize, perceive, and experience group work. Three research questions guided this study: (a) What are the experiences of secondary school counselors who conduct groups?; (b) What are secondary school counselors’ attitudes and perceptions towards group work?; and (c) What do secondary school counselors perceive as barriers and /or challenges to engaging in group work? Data were collected in three phases: Phase One, an initial focus group informed Phase Two of the study, individual interviews. Phase Three, member-checking, was used to validate themes generated from data analysis. Moustakas’s (1994) transcendental phenomenology guided the data analysis process. Findings revealed four themes associated with participants’ group work experiences: meaningful relationships, staff response, challenges, and encouraging feedback. Practical and research implications for secondary school counselors and counselor educators are discussed.