This chapter addresses the issue of how traditional design studios tend to foster tacit knowing, which is an aspect of being designerly. However, novice designers may lack sufficient design experience to translate intuition into rationalized heuristics or short-cuts of practice. The first Case in Point outlines how design educators could help students form design thinking through supporting them with heuristics about deconstruction practices across the semester. The second case exemplifies how changes to the studio environment and creative exploration processes helped printmaking students to develop design thinking through taking charge of formulating their own heuristics. In this way, students could transfer their personal ‘productive trial-and-error’ beyond current course contexts.