The decisions that managers make can be influenced by a number of factors. The current study examines two specific organizational factors (judgment intent and evaluation expectancy) and two task demand characteristics (situational risk and workload) that might influence the consistency, accuracy, timeliness, and quality of managerial decisions. Analysis of Variance (ANOVA) and Analysis of Covariance (ANCOVA) results reveal that these factors do have significant influences on various aspects of managerial decisions. Most notably, the expectation of evaluation was revealed to both help and hinder decision-making, dependent on other contextual factors and situational risk consistently led to better decisions. Implications are presented for addressing these factors and helping managers make the best decisions under certain organizational and situational constraints.