Although there is a significant body of research evaluating the potential effectiveness of parent involvement programs, little research has studied effective methods to reach non-traditional caregivers, specifically grandparents. The purpose of this study is to examine how grandparent caregivers in a particular setting consider the barriers to, and facilitators of, meaningful engagement at the school level. As the first stage in an iterative participatory action research project, the research team conducted a series of interviews to facilitate the co-definition of grandparent engagement issues at a middle and high school. The results offer initial insights as to the importance of listening to grandparent caregivers when seeking to determine the facilitators of, and barriers to, school involvement. These results will be used to further engage the grandparent and school communities in the development of context-specific strategies intended to inspire the meaningful engagement of grandparent caregivers.