The paper suggests a focused examination of the processes of drafting-based design and parametric design in urbanism. It discusses how spatial design’s settled cognition would differ by using algorithmic systems through the altered relationships between the basic operations in design. To reveal the commonalities and distinctions between the two design methods, the authors present the detailed documentation of the workshop series, which experimented with both techniques within similar design contexts. By the design analysis, the idea of “parametric thinking” is revisited in the specific context of urban design.