As online learning becomes a strategic focus of colleges and universities, the effectiveness of online education administrative leaders assumes an increasingly critical role in achieving institutional goals. In this article, the author uses a critical theory lens to understand how online education administrative leaders in higher education institutions negotiate the various political challenges to promote effective practice. The study found that online education administrative leaders work to build relationships, build credibility and trust, find common ground, use data to drive change, and empower faculty. Negotiation tactics are situational and contextual.