In this paper, we examine skill-related uncertainties among middle managers during organizational change. The question emerged from a qualitative study of two planned organizational change initiatives in the public sector where a group of middle managers were required to learn new skills because of changes in their work tasks and managerial roles. In both cases, we found that change recipients experienced two types of job-related uncertainty in the post-training phase: role ambiguity and operationalization uncertainty. Role ambiguity refers to challenges in understanding diverse expectations tied to the future work situation and necessary skills, whereas operationalization uncertainty refers to the challenges of putting new skills into practice. Although necessary and important, formal training was not sufficient to resolve these challenges. Rather, the change recipients engaged in informal and horizontal communication to resolve uncertainties related to new skill and role requirements.