As transgender individuals receive more attention nationwide, it is only a matter of time before increased numbers of transgender educators seek placement in teacher education programs, and eventually, employment as teachers. Given the high levels of discrimination against transgender individuals historically, it is reasonable that P-12 school leaders and educator preparation programs (EPPs) would seek to proactively determine obstacles that may exist when placing transgender teacher candidates (and future employees) in schools for field experiences. The researchers for this study engaged in a qualitative approach, interviewing 14 school leaders in seven different districts on their attitudes regarding field placement and possible hiring of transgender teacher candidates. Emerging themes noted that while school leaders expressed an appreciation for diversity, they believed the presence of a transgender teacher candidate would stimulate resistance in their local communities. Further comments by participants indicated a need for training to provide leaders with guidance on navigating these issues, as well as training to better understand the transgender experience.