Managerial constraint is a central theme in strategic management research. Although discussed using a variety of labels (including choice and determinism) and theoretical perspectives (including resource dependence and population ecology), the common question is the degree to which executives have choices or options when making decisions. Two of the most commonly used approaches for discussing constraint are organizational task environments (Dess & Beard, 1984) and managerial discretion (Hambrick & Finkelstein, 1987). These two papers share substantial commonalities in both their theoretical background and operationalization, raising the question of whether discretion and task environment are indeed separate constructs. This chapter reviews both conceptual and methodological issues associated with the use of task environment and discretion. Drawing on a review of published studies and original data analysis, we offer methodological suggestions for future research.