A while ago, the author and his wife, Shari, were charged with the daunting yet intriguing task of planning and implementing a multiweek short-term study abroad course in Wales. One of their first tasks was to select a student as assistant leader for the trip. This student would be responsible for a great deal of work throughout the semester leading up to the expedition and would be an integral part of the leadership team while they were in Wales. This was a huge opportunity for an undergraduate, and it was vital that they select the right person. From the many excellent applicants among Shari's community service and service-learning student leaders, they narrowed their choices to two quite different but nearly equally qualified young women. The couple had to make a difficult decision, but his wife suggested leaving the decision to the students. The author, however, was bothered by the outcome of this suggestion. In this article, the author shares how he confronted his trust issues by giving these students a chance to decide which one of them was the best fit for the trip.