Not long after Dennis Roseleip received a superintendency appointment in his native state of Montana, the district's entire administrative team departed, leaving him to fill three principalships in the opening months of his new post. The sudden vacancies were not a statement on the choice of Roseleip, then 44, to lead the Cut Bank Public Schools in Glacier County, Montana. One elementary principal retired, another left for a superintendency. The high school job was the one he vacated. So Roseleip used the rare opportunity to rebuild the administrative team from scratch to show off the true colors of his leadership style and to separate himself from the autocratic decision-making approach of his predecessor. This article contains a brief profile of Dennis Roseleip and discusses the work that he has done as a superintendent.