Some communities are collaborating with local leaders to improve relationships between authority figures and the communities they serve. This strategy builds on empirical successes as well as a theoretical tradition extolling the role of intermediary actors in bridging disconnected groups. In this paper, I problematize the expectation that individuals can fully span boundaries in situations of cultural difference and inequality. I draw from semi-structured, in-depth interviews with 14 community leaders from a variety of backgrounds, whom I call boundary-spanning actors (BSAs), to show that BSAs are rarely positioned to engage effectively with both authority figures and at-risk individuals, but instead position themselves at the boundary of one group. I distinguish between two ideal types of BSAs, the professional-advocate and the mentor, and show how a BSA's personal experiences, individual skills, and existing relationships lead to distinct credibility claims, and persuasive and practical strategies.