Parent involvement has increasingly been mandated as a key component of school reform, and school-community relations courses (as well as standards for administrators) call for collaborating with diverse families and communities. Yet the role of school leaders in engaging parents is underdeveloped in the literature and in preparation programs. How do leaders envision parent engagement and construct their role in promoting it in a large urban district? What contextual factors enable and constrain leadership for parent engagement? This qualitative study of 12 urban administrators known for their commitment to parent engagement shows how their leadership style promoted a family-friendly climate but fell short of the comprehensive partnerships and shared leadership models envisioned in the literature. Implications for preparation programs are discussed.