A growing body of research documents the importance of studying job embeddedness in order to predict turnover, or conversely, why employees stay at their jobs. However, little is known about how meetings—one of the most time-consuming practices at work—might be related to job embeddedness. Grounded in job embeddedness theory, I examine how the occurrence of a particular type of meeting—skip-level meetings, or meetings with one’s supervisor’s supervisor, relate to job embeddedness. The present cross-sectional study examines this relationship along with detailed descriptive information concerning skip-level meetings. Additionally, a moderation analysis was conducted to ascertain the potential moderating effect of discussion content on the skip-level meetings and job embeddedness relationship. The implications of these findings for organizational practices and employee engagement are discussed, emphasizing the role of skip-level meetings in fostering job embeddedness and overall employee well-being.