The past decade has witnessed a strong, standards-based call for improving what mathematics is taught and how it is taught. In the USA, districts have hired instructional coaches to help teachers shift their teaching from algorithm-based instruction to instruction that is more student-centered and conceptually focused. The purpose of this study was to contribute to the field’s understanding of (a) the specific coaching practices that help teachers enact more conceptual-based forms of instruction; and (b) how coaches learn to enact those practices. Using a design-based implementation research approach, we trained coaches using a particular model for one-on-one coaching (Content-Focused Coaching); the coaches then worked with teachers to plan lessons aligned with the coaching model. Data consisted of videotapes of pre-lesson conferences that were transcribed and coded according to the model. Analyses of 32 coaches’ practice over a 2-year period suggest that each of the three components of our coaching model (attention to student thinking, pedagogy, and mathematics) demonstrated statistically significant improvement over time. An illustrative analysis of five coaching sessions of one coach revealed a progression over five sessions from planning discussions that stayed at the level of general strategies to more specific conversations about teaching a particular task and then to deeper discussions that integrate attention to mathematical concepts, student thinking, and pedagogical moves. We view this delineation of coach learning as an important first step in laying the groundwork for the design of future coach training.