Designers create and evaluate a large set of design alternatives in generative design. Navigating large design spaces presents considerable cognitive and practical challenges, necessitating a new class of tools to manage these alternatives. Interactive data visualizations are integrated into design environments to augment or complement existing tools for applying segmentation strategies, such as simplification. Despite their benefits in filtering and sorting, designers often face difficulties making sense of alternatives due to complex workflows and limited designer-friendly features. This paper identifies opportunities for ‘simplification’ of design space navigation tasks through task-tool matching by conducting an expert user study using a Design Space Exploration (DSE) tool, DesignSense, which offers advanced features, such as clustering, coordinated views and set operations. We analyzed the data in two levels: task-based and feature (tool)-based. The study’s qualitative analysis revealed different flow patterns of interactions with the tool. Based on our findings, we demonstrated enhanced set-based operations extending D-Sense, showing how such patterns of flows can be supported in DSE.