This dissertation presents the results of three studies designed to enhance understanding of how individual risk evaluation pertains to role theory and how prospect theory can offer clues on the process undergirding the translation of employee role expectations into behavior in the workplace. In studies 1 and 2 I develop a novel scale for evaluating employee risk-related role expectations. Study 3 draws on a sample of 439 working adults and examines how coworker general (non-work-related) risk propensity affects employee’s role expectations regarding risk and expectations of coworker approval. Further, I explore the linkages between employee expectations and subsequent behavior and the influence of coworker indicated approval. Integrating prospect and role theories, I find support for the hypothesis that coworker risk propensity has a negative relationship with employee risk-related role expectations, and expectations of approval. I also find support for the positive relationship between employee risk-related role expectations and behaviors, and mixed support for the positively moderating role of coworker indicated approval. Implications for theory and practice are discussed along with directions for future research.