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Disconnection from school among young children can persist and have negative long-term consequences for motivation and achievement. The Check & Connect (C&C) monitoring and mentoring program addresses student school performance by building supportive relationships between at-risk students and monitors focused on school engagement. A randomized control trial of C&C was implemented in the Chicago Public Schools (CPS) with 450 students in 23 elementary schools working with 15 full-time monitors. We use administrative data and in-depth interviews with monitors to examine implementation of C&C including how monitors spend their time and what activities they engage in. We find substantial variation across monitors in terms of how they view their role and in how they interact with and spend time with students.