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Educational leaders - including department heads, principals, central-office administrators, and others with positional or reputational authority – face myriad challenges. Some are mundane, such as negotiating contracts with vendors. Others are extraordinary, such as helping the community recover from a tragic illness or death. The solutions to some challenges are relatively straightforward. This does not mean they are simple, but simply that the path is relatively unambiguous. By contrast, the most vexing challenges pose dilemmas. Dilemmas are complex, have no clear “right answer,'' and call for nuance, discernment, and compromise. Demanding judgment amongst competing goods, dilemmas present ethical challenges. The purpose of this paper is to present a novel project seeking to help novice educational leaders navigate ethical dilemmas.