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Cheating is ubiquitous in individuals, families, social groups, and organisations but the motivations to cheat remain unexplained. Psychoanalysis’ focus on the superego and related moral weaknesses and the economic theory of a simple risk-reward calculation have given way to an understanding that a biological predilection to cheating exists and that everyone cheats at least a little. Modern neuroscience has also identified factors that influence cheating behaviours. Lessons from contemporary treatment of latency-age children and from a linguistic approach to intersubjectivity converge to conceptualise cheating as a complex internal struggle; one involving narcissistic, omnipotent, magical thinking focused on the self on the one hand and real world actions that take others into account on the other. Combining the tenets of the various disciplines yields methods for organisations to manage extreme cheating in an evidenced-based manner that addresses underlying mechanisms and dynamics. The mental mechanics of cheating are also in evidence in the psychology of everyday life and are employed by leaders to maintain a balance between competition and connection to others and to promote play, creativity, and innovation. Tracking and managing this “double-edged” developmental process presents a constant workplace challenge. “Cheating management” qualifies as a fundamental, but overlooked, aspect of leadership.