Schools are demanding ever more sophisticated executive skills from heads these days. As a result, the headship position is beginning to resemble that of a "chief executive," while at the same time retaining all of the academic and interpersonal components of the past. Many schools require their heads to at least understand, if not be proficient at, debt financing, business modeling, labor negotiations, working with municipal planning and zoning boards, construction management, and more--skills that would only rarely have been called for from earlier generations of school leaders. The growing complexity of the job means that those educators interested in school leadership in the near future need to think carefully about their route to the headship. It also means that the independent education community in general needs to be more intentional about nurturing its next generation of leaders. In this article, the authors discuss the path to headship and the intentional preparation for headship.