Research shows that conversations and daily interaction among teachers and children is crucial for their development. Observing children and interpreting their thinking processes is a significant factor in intentionally planning curriculum that emerges from children’s thinking, assists them in making connections, and extends their learning. This article presents findings of a single case design study investigating the effects of the observation and interpretation processes in a Cycle of Inquiry System (COI) (Broderick and Hong in Early Childh Res Pract 13:1–14, 2011) intervention on preschool teachers’ productive conversations with children. The intervention for each teacher consisted of pre and post interviews, a 1-day COI training, use of COI observation and interpretation forms, and coaching meetings with the researcher. The participants were 4 preschool teachers in Northeast Tennessee. Teachers were videotaped in their classrooms working with children during the free play time and coded for productive and non-productive conversation strategies for determining the baseline and changes during the intervention. All the teachers show an increase in productive conversation strategies to differing degrees. The non-overlapping pairs analysis for all participants is represented by a large value. The findings indicate the benefit of training teachers to observe and interpret the meaning of children’s conversations to intentionally plan for productive conversations that impact learning.