To create and sustain high quality youth development programs it is important to understand the challenging situations and dilemmas that emerge in program leaders' daily work with youth. In this research the experiences of leaders in 12 programs were followed over a 2-9 month period, which led to the identification of 250 dilemma situations. Qualitative analyses identified 5 categories and 12 subcategories of dilemmas that reflected distinct types of considerations (e.g., youth's personalities, relationships with the community). The analyses also found that the experienced leaders in the study typically responded to these dilemmas in ways that were youth-centered and that balanced multiple considerations. It is argued that researchers need to go beyond identifying features of high quality programs, and more fully examine how effective leaders create and sustain high quality in response to the challenging situations of practice.