Productive mathematical conversations are a significant component of developing students' mathematical understanding and ability to effectively communicate their thinking, and the types of questions teachers ask can either hinder or advance that development. Seeking to understand students' thinking while monitoring their initial work on a task better equips the teacher to purposefully select and sequence students' ideas. This, in turn, can better support meaningful mathematical connections among students' work, which provides for a more productive discussion. This article provides vignettes that are a compilation of common themes that the authors have observed in their work. These themes are evidence of the need to focus on thoughtful planning for quality questioning in mathematics instruction.