Leader behavior can vary daily, and leaders face multiple demands and problems in one day. Therefore, studying how leader behaviors interplay on the day-level (i.e., daily leadership profiles) is essential. Building on conservation of resources theory as a meta-theory, we investigated which daily leadership profiles exist and whether profile membership changes across one week. Additionally, we examined whether the leadership profiles are differentially related to leaders’ daily well-being (i.e., emotional exhaustion, positive and negative affect), mediated by their daily experienced thriving and time pressure. In a diary study over five workdays (N = 289 leaders), we found three qualitatively different daily leadership profiles: one dominated by passive behaviors (passive), one dominated by transformational and contingent reward behaviors (transformational-rewarding), and one with elevated transformational and all transactional behaviors (comprehensive). The transformational-rewarding and the comprehensive profile showed greater stability across the week than the passive profile. Days in the transformational-rewarding profile were most beneficial for leaders’ well-being. In contrast, days in the comprehensive profile seemed to be a double-edged sword for leaders, as indicated by higher experienced thriving and positive affect and simultaneously enhanced experienced time pressure, emotional exhaustion, and negative affect. Taken together, we illuminate the interplay of leadership behaviors on the day-level and the differential associations with leaders’ well-being.