We use different criteria to judge teaching methods and learning environments as researchers and teachers. As researchers, we tend to rely on learning gains measured in controlled conditions. As teacher, the skilled management of classroom constraints results in the impression that a specific design “works well”. We describe fourteen design factors related to the metaphors of classroom orchestration and education ecosystems and illustrate their embodiment in three learning environments. These design factors provide a teacher-centric, integrated view of educational technologies in the classroom. We expand this list of factors to include the main constraints that designers should consider to address the difficult methodological issue of generalizing research results about the effectiveness of methods and designs.