Learning assessment constitutes an essential pedagogical ability in a teacher’s toolbox in order to further student learning and development and to adapt teaching to the needs of the students. To enable this, learning outcomes and grading criteria are used in the formative assessment of students’ performance to support the learning process, as well as in the summative assessment of the actual outcome for grading. Learning outcomes may be represented in various forms, typically scoring rubrics. Current research literature discusses the positive and negative merits of criterion-based scoring rubrics versus holistic assessment. There is also the matter of grading reliability among teachers and a shared understanding of student performance among teachers and students. Digitalization has become an essential part of higher education and distance learning, especially so in our field of digital design. A relevant issue in this context is how digital solutions may enhance formative learning assessment in particular. As is common practice within our field, within the study we designed, developed, and experimented with a digital tool in the form of a visual radar chart representation. The radar chart was based both on work done by teachers and a student thesis work and was used in several courses for teacher assessment as well as self- and peer assessment by students. This work provided the opportunity for reflection as well as analytical assessment, which in turn had the potential in guiding teachers to critically question and discuss the intended learning outcomes and grading criteria. The study has resulted in a variety of identified problems, reflections, and insights that teachers are continuously confronted with, but not necessarily always conscious about when using intended learning outcomes as a basis for communicating formative assessments to students. By visually and holistically communicating students’ strengths and areas for development over time, we found the potential to increase students’ shared awareness of their learning progress and also further the development of curricula. The study has implications for teacher and student awareness of student performance and learning, curriculum development, and digital assessment tools.