Though a variety of studies have considered the impact of mentoring on beginning teachers, there is little research that explores effective ways to support their work. This qualitative study addresses that gap in the literature by describing how one mentoring program sought to develop mentors' understanding of their local context by sharing elements of asset-based pedagogies and by engaging community members in the training process for new mentors. Initial interviews revealed that most mentors viewed the community through a deficit lens. Even after engaging in conversations with local stakeholders and learning about community resources, mentors indicated that little changed with respect to their perspectives of--and practices in--the community. We consider reasons for the program's limited success and discuss implications for programs that seek to develop mentors who actively engage with the school community in ways that value stakeholders' assets and experiences.