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Drawing on observations from structure-agency theory and interview data from eight schools in a unionized school district, we provide a first-hand perspective on the interactions between administrators and teachers around the collective bargaining agreement (CBA). Importantly, the last interview paper that documented school leader perspectives on CBAs was published over 20 years ago when its author acknowledged that “principals are reluctant to speak frankly on the subject (Ballou, 2000; p. 91).” To take advantage of this empirical opportunity and to fulfill both descriptive and theoretical agendas, we ask “How do school leaders implement collectively bargained terms in everyday contexts?” We show that leaders’ choices on CBA implementation were shaped by the social dynamics at their school.