Aspiring leaders need guidance, and there is no shortage of advice on the qualities required for successful leadership. Moral philosophers in the Western tradition have tended to gravitate toward the moral end of the spectrum. Seeking to dominate others can certainly work, but too often it supports leadership styles that are short-sighted and self-destructive. Many thinkers have counseled that society should embrace the virtuous approach to leadership. Emphasizing the importance of virtue for leadership is entirely appropriate: moral virtue is crucial for strong leadership. The concern Mark Piper wishes to explore in this article, however, is that the qualities that make one morally virtuous and the qualities that make one an effective leader are not infrequently at odds with one another. If this is the case, then virtue-heavy leadership guidance may be of rather limited value to those who are seeking to be not only admirable, but also effective leaders. In this article, he argues for these claims and suggest how models of successful leadership can be modified to be of greater practical value to persons seeking leadership advice. The most useful approach to leadership guidance will provide leadership guidance in the gray areas between moral virtue and effectiveness.