This article is a critical retrospective account of the decisions made by a team of evaluators contracted to assess a week-long leadership program for high school youth. The program planners all sought to prepare community youth leaders to foster the freedom of religion, but they varied in how they believed this ought to be achieved. The ethical dilemmas discussed in the article focus on the authors' choices of engagement or non-engagement as they strove to understand different stakeholders' perspectives, while also witnessing events that challenged their own perspectives of the program.