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The workplace is a complex setting that includes the dynamic interaction of human nature with the need to produce something of social value in order to survive in the marketplace. The participant-observer of organizational life is eventually swept along in this current of complexity. Diagnostic frameworks facilitate sense-making of this experience and data. This paper provides a four-part typology of organizational diagnostic disorders (narcissistic, arrogant, dependent, avoidant) into which may be placed much of what one learns from participant observation of organizational life. This diagnostic matrix is a step in the direction of providing a psychodynamically informed and systematic approach to understanding organizational life.