This case study, framing teaching as a dialogic relationship between teachers and students, investigates how educators can learn how to manage the complexity of instructional decision-making through a professional learning routine. The study analysis examined how the "Teacher Time Out" routine, when embedded within collaborative teaching environments, allowed educators-school leaders, teachers, and university faculty-to engage with the unpredictability of classroom interactions alongside their colleagues and students. Through this process, educators were able to inquire into mathematical ideas with students, respond to the particulars of students' mathematical thinking, enact shared cultural values, and develop pedagogical judgment to inform future teaching decisions. Using a sociocultural perspective on teacher learning, this case study highlights how pauses during instruction enabled educators to reflect on their practice, collaboratively reaching instructional decisions in the moment and reflecting on them after the teaching enactment. The study contributes to the literature on professional learning, showing the potential of routines such as Teacher Time Out to support teachers in learning both from and with their students during the dynamic process of teaching.