Every year, new graduates enter the workplace with great expectations for their careers. For many, the transition from school to work is challenging as they learn to fit into their new roles and organizational settings. Often, they find this experience to be not what they expected and experience feelings of frustration, uncertainty, or disappointment in their new jobs. This article reports on the socialization experiences of 41 newly hired engineers and 15 of their managers in three different organizations. Using an inductive, qualitative approach to collecting and analyzing in‐depth interviews, the findings indicated that socialization processes, designed to help newcomers learn about and integrate into new jobs, are more ambiguous and difficult than many newcomers and managers expected. We found that the best intentions of some managers and newcomers were misinterpreted and thus fell short of expectations. The findings indicate how the misinterpretations of newcomers and managers negatively affected the quality of learning, performance, and satisfaction during socialization. The implications of these misinterpretations point to crucial gaps in the educational preparation of graduates for the workplace and shortcomings in the socialization or onboarding of new hires in organizations.