Learning design is a research field which studies how to best support teachers as designers of Technology Enhanced Learning (TEL) situations. Although substantial work has been done in the articulation of the learning design process, little is known about how learning designs are experienced by students and teachers, especially in the context of schools. This paper empirically examines if a teacher inquiry model, as a tool for systematic research by teachers into their own practice, facilitates the connection between the design and data-informed reflection on TEL interventions in two school communities. High school teachers participated in a learning design professional development program supported by a web-based community platform integrating a teacher inquiry tool (TILE). A multiple case study was conducted aimed at understanding: (a) current teacher practice and (b) teacher involvement in inquiry cycles of design and classroom implementations with technologies. Multiple data sources were used over a one year period including focus groups transcripts, teacher interview protocols, digital artifacts, and questionnaires. Sharing teacher-led inquiries together with learning analytics was perceived as being useful for connecting pedagogical intentions with the evaluation of their enactment with learners, and this differed from their current practice. Teachers' reflections about their designs focused on the time management of learning activities and their familiarity with the enactment and analytics tools. Results inform how technology can support teacher-led inquiry and collective reflective practice in schools.