This article aims to explore how distinct conditions affect qualitative differences at the micro level in middle leaders’ communicative practices for leading professional learning and development. Research on this subject is sparse. In a previous study, we explored how different leading practices formed what we call a web of leading, working towards the common goal of leading and developing teachers’ professional learning. We identified differences in the conditions–that is, the practice architectures–for two middle leading practices. In the present study, we strive to examine how the identified differences affect middle leaders’ communicative practices. Drawing on the theory of practice architectures and on quality aspects in communication for learning, we conducted a comparative analysis. The findings illustrate the qualitative differences in middle leaders’ communicative practices and their actions when leading and facilitating professional learning. The article concludes that different conditions for middle leading practices have a decisive influence on the quality of conversations for professional learning, indicating that they might have a decisive influence on the legitimacy of middle leaders.