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Like it or not, abnormal behavior is more 'normal' than most people are prepared to admit; all of us have a neurotic side. Drawing on clinical data and psychoanalytical concepts, the authors of this chapter explore the following questions: Is the typical executive really a logical, dependable human being? Is management really a rational task performed by rational people according to sensible organizational objectives? They undertake a psychoanalytically informed investigation to discover how people and the organizations they work in really function, highlighting the importance of three triangles: the mental life triangle, the conflict triangle, and the relationships triangle. The chapter concludes with ideas about how to design and deliver a transformational leadership program within the context of a business school that encourages future executives to look into the original sources of their behavior and start the process of self-exploration. This chapter was originally published as Chapter 7 of 'Handbook of Leadership Theory and Practice: A Harvard Business School Centennial Colloquium.' This chapter is excerpted from ‘Handbook of Leadership Theory and Practice: A Harvard Business School Centennial Colloquium'.