Employees often have to decide whether to conform to or deviate from the status quo. Exhibiting consistent preferences for either preserving or maintaining the status quo (i.e., conformity biases) or for challenging or rejecting the status quo (i.e., deviation biases) can be costly. Conformity biases prevent employees from adapting to changing task demands and deviation biases hamper the predictability and reliability of decisions. It is therefore important for scholars and practitioners to understand how to engineer work environments that, to the degree possible, enable employees to bring down both types of risks. However, our understanding of this issue is limited because organizational behavior researchers to date have focused on reducing conformity biases but slighted the opposing risks of deviation biases. This dissertation is dedicated to filling this gap. Challenging research on the benefits of congruent work environments that send consistent normative signals, I demonstrate how congruity can push employees into stable patterns of conformity or deviation whereas incongruity can trigger more flexible thinking that enables employees to reduce both biases. Chapter 1 examines how incongruent combinations of distributive justice systems and cultural values--egalitarian-individualist and meritocratic-collectivist--tamp down both risks by encouraging employees to fluidly shift between loss-minimizing and gain-maximizing frames. Chapters 2 and 3 present two laboratory experiments that demonstrate how incongruent combinations of cultural values and accountability systems-- collectivist values / outcome systems and individualist values / process systems--can also control exposure to both risks by encouraging decision makers to iterate between the micro details and big picture. Finally, Chapter 4 investigates how blends of cultural values and accountability systems shape managerial tolerances for employees who exhibit conformity or deviation biases. In a field study of working supervisors, I show that managers in congruent combinations--collectivist values / process systems or individualist values / outcome systems--either prefer conforming employees or deviating employees, respectively, but managers in incongruent combinations have no discernible preference. Overall, this dissertation offers novel ways to offset the risks of various organizational systems and encourages the field to reassess the benefits of intrapsychic conflict in light of the clashing demands employees confront today.