The purpose of this paper is to advance an approach to analyzing decision-making by front line public officials. The notion of discretion in front line decision-making has been examined widely in the law and society literature. However, it has often failed to capture the different kinds and levels of decisions that enforcement officials make. Taking an interdisciplinary approach that draws on political, sociological, and legal analysis, we propose a new conceptual framework, one that draws a sharper distinction between discretion and judgment and teases out distinct levels in the scope and depth of decision-making. We then use this framework to create a conceptual map of the decision-making process of front-line officials charged with enforcing the Employment Standards Act (ESA) of Ontario, demonstrating that a deeper, more precise analysis of discretion and judgment can contribute to a richer understanding of front line decision-making and its social, political, and legal implications.