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The Chief Executive Officer (CEO) of any organization, by the nature of his or her title and role, sets the culture (the “how we do things around here”) which becomes either paranoiagenic or trust-inducing to greater or lesser extremes. This account of one CEO emphasizes the relationships between past managerial experiences, the business requirements of a highly competitive industry, the nature of the impact of local government on globally dispersed installations, and an intense interest in bringing together a better understanding of trust-inducing top-down managerial leadership. Thus follows an examination of one CEO's journey with a nascent body of research and the researcher as, together, they struggle with understanding what requirements and actions will be interpreted as not only “good for the company” but also “good for me” as an employee. The paper describes the added value of a CEO's systematic organizational analysis and structural design of a managerial work system focused on the employment of the discretion and judgment of each employee within appropriate role boundaries, thereby inserting a large amount of psychologically sound, creative problem-solving focused on competitive business outcomes. It develops understanding of the business reasons for fair pay for levels of work assigned, and the recognition of current potential capability and development of individuals as they naturally mature in future potential capability to handle more complex assignments.