Understanding the basics of how organizational realities get formulated is probably the ultimate skill that managers need to develop. In addition, there are other less sophisticated but equally important skills that should be acquired to avoid repeating the blunders of the seventies. This article describes some of these skills and articulate specific dilemmas management educators face when trying to teach them. One of the overriding dilemmas relates to the difficulty of getting students to ground the teachings in their own experience. Another stems from how educators have been trained to take their roles in the system. The various skills to be taught and dilemmas in teaching them are skills for interacting with authorities and people of power who are competent, perhaps charismatic, but not perfect, skills for living with uncertainty and openendedness, for asking questions which can't be answered today, skills for resisting elitist thinking and learning from the experiences of others, skills for describing managerial styles and charting directions for personal development, skills for piecing out and explicitly dealing with the subjective components of "objective" decision making, skills for creating organizational justice and practicing due process.