Leading American schools is a multi-faceted and complex role as states have adopted requirements for the mentoring of new principals. Interactive problem-based simulations can offer novice principals opportunities to practice solving job-embedded issues. This study explored practicing administrators interacting with simulations embedded into an existing mentoring program. The perceptions of participants reveal that simulations could be used widely in a school district for professional development, personalized to the needs of the district. The same simulations could also be used during internship component of principal preparation programs. Future school leaders could explore current problem based scenarios in a risk free environment.