Learning Design (LD) research accounts for several design support tools, or LD tools, employing representations for learning designs to facilitate the “teachers as designers” thinking while preparing learning experiences. In contrast to existing studies having followed mainly a specialist/researcher (as opposed to a teacher) perspective, our quest to develop an LD tool follows a Design-Based Research (DBR) approach involving practitioners. Specifically, in this paper, we attempt to give voice to teachers as designers and investigate how they prefer having their learning designs represented by LD tools. Aiming to create a principled account of how to represent learning designs in an LD tool, we first conducted an integrative literature review to formulate a representational framework that drove our research. Subsequently, we addressed the following LD representational dimensions: (i) format, (ii) organisation, (iii) guidance and support, and (iv) contextualisation. We are reporting on a case study conducted with 16 participants in a teacher education context. Although previous research typically reported findings based on a single LD tool’s evaluation over a short period, we have opted for eliciting feedback based on a rich LD experience. To this end, we acquainted participants in LD projects with two LD tools (Learning Designer and WebCollage) during an academic semester. Furthermore, we followed a mixed-method explanatory sequential design applied through a survey questionnaire and semi-structured interviews to achieve a more profound consideration of the teachers’ preferences for LD representations. Our findings indicate that the teachers strongly endorse an LD tool supporting a visual format and a global organisation in the form of a table that provides a global overview of a learning design while focusing on its specific elements. Teachers seem to prefer an LD tool that balances providing guidance and flexibility, as they opt for (i) a non-restrictive taxonomy for articulating learning objectives, (ii) some form of standardisation for formatting learning units, along with allowing free formation, (iii) a flexible pedagogical framework for modelling the learning activities’ pedagogy so that it can be adjusted to particular designers’ needs, and (iv) a typology of technologies that can be utilised or not. In addition, they seemed to favour an LD tool supporting high contextualisation, as they prefer to describe contextual details for a learning design’s units and activities. These findings constitute design principles for our ongoing DBR and may stimulate momentum for researchers developing LD tools.