Organizations often struggle to engage their workforces despite various known benefits and predictors of employee engagement. The current study examined a new approach to promote employee engagement—1:1 meetings between managers and direct reports—which are commonly occurring, theoretically relevant, and understudied. Leveraging job-demands resources theory and self-determination theory, it was hypothesized that the quantity (i.e., frequency) and quality (i.e., presence of manager task- and relations-oriented behaviors) of 1:1 meetings promote direct report engagement by satisfying direct reports’ basic psychological needs for autonomy, competence, and relatedness. The proposed moderated mediation model was tested with data collected from two time-separated online surveys (N = 303). Results suggest that 1:1 meeting quality—particularly manager relations-oriented behaviors—plays a stronger role in promoting direct report engagement as compared to 1:1 meeting quantity with the important caveat that 1:1 meetings happen at least monthly. Results also suggest that 1:1 meetings are conceptually distinct from and can promote direct report engagement beyond other manager-direct report meetings and interactions (e.g., email exchanges, team meetings) by better supporting direct reports in a synchronous and individualized manner. Taken together, the current study supports 1:1 meetings as a critical tool managers can leverage to promote their direct reports’ engagement, while also contributing to both the meeting science and engagement literatures.