In this study we will open the black box of problemistic search by documenting a variety of narrow and broad search strategies individual decisionmakers undertake in a process of a firm’s goal attainment. Several commentators have argued that the notions of narrow vs broad search are underspecified and dependent on the ambiguity of the goal and the of environment. This study joins these studies that argue that ambiguities between outcomes, aspirations and decisions will affect the search strategies. In this study we will focus on the question whether ambiguity in goals and outcomes leads to diversity in directions of search strategies. We will explore our contributions with a purpose-built virtual reality (VR) experiment, a research method that opens the possibility to study individual internal sub-processes of problemistic search under conditions which are difficult to control in a non-experimental setting and allows us the development of the data collection for individual problemistic search. Our study responds to the call for research in decision-making in behavioral organizational theory, culminating in a research agenda that further develops VR research for organizations. We will conclude that this study contributes to the behavioral theories of organizations by enriching our understanding of search processes.