Many states are mandating reforms in university-sponsored principal preparation programs, but faculty and school system personnel often have concerns about the prescriptive nature of state mandates related to these reforms. Auburn University served as one of four pilot principal preparation program redesigns in Alabama, a process that took over two years. Redesign efforts involved negotiating state requirements, faculty needs and research interests, school district needs and interests, best practices, and common sense. The re-design was developed and is being implemented in partnership with seven school districts. In this article we interrogate the issues, challenges, and successes faced throughout one university's principal preparation program redesign process, offering reflections, insights, and lessons learned for others currently engaged or soon to be negotiating competing agendas for how they should prepare principals.