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—which are commonly occurring, theoretically grounded, and understudied. Leveraging job-demands resources and self-determination theories, 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. 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 these meetings happen at least monthly. Results also suggest that 1:1 meetings are conceptually distinct from and can promote direct report engagement above and beyond other manager-direct report meetings and interactions by better supporting direct reports in a synchronous and individualized manner. 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.