This chapter examines some elements of the conflicts that give rise to dilemmas for project managers. As project managers and Program Management Office (PMO) practitioners, we continually strive to improve our performance by reflecting on those areas where we excel, and critically review areas where we could create more desirable outcomes when faced with similar circumstances. When facilitating the project Closeout and Lessons Learned process, the project manager faces many choices and dilemmas on his journey to actionable project Lessons Learned. Dilemmas arise from internal or external conflicts between goals, values, perspectives, and points of view. Dilemmas provide learning and growth opportunities for project managers to review and choose a course of action. John C. Maxwell, who is known as a present-day guru of leadership, has often been quoted as saying that "leaders have choices and when they make those choices, the choices in turn make them".