Clinical simulations provide opportunities for novice school leaders to synthesize and enact their professional knowledge, decision-making approaches, and skills in an authentic, challenging environment. This article outlines the use of clinical simulations and standardized individuals to enhance and extend the preparation of novice school leaders. Modeled directly from medical education's use of standardized patients, school leader participants engaged with a standardized father who strongly challenges a unit of instruction on reproductive education. In real-time, in front of the standardized father, each school leader must navigate requests for an alternative assignment, demands that the unit of instruction be removed from the school entirely, and questions on the morality of offering the curriculum. Implications address the school leaders' different, individual approaches to this shared, clinical experience, but also emphasize the broader use of clinical simulations in the preparation of teachers for both general and content-specific contexts.