Upper echelon in organizations must effectively lead middle managers (MM)—central linking pins in strategy processes—but also retain them for loss of their human and social capital can threaten strategy implementation. While long envisioning how leaders motivate subordinates to stay, management scholars have largely neglected how leaders' own teams constitute an organizational context moderating their ability to retain subordinates. Building on a recent micro-level model that leader humility discourages subordinates from voluntarily departing by increasing their job satisfaction, we propose that faultlines in top management teams (TMT) can exert cross-level effects attenuating how humble executives sustain MMs' job satisfaction and how MMs' job dissatisfaction drives their voluntary turnover. A multisource, multiphase dataset of 43 TMTs, 313 top executives and 502 middle managers supports our hypotheses. Our study bridges the macro and micro divide to offer a multilevel inquiry into contextual influences on voluntary turnover, identifies a boundary condition for leader humility effects, and clarifies how TMT faultlines can invoke a detrimental context hindering top executive - MM relationships.