Very soft grain assemblies have unique shape-changing capabilities that allow them to be compressed far beyond the rigid jammed state by filling void spaces more effectively. However, accurately following the formation of these systems by monitoring the creation of new contacts, monitoring the changes in grain shape, and measuring grain-scale stresses is challenging. We developed an experimental method that overcomes these challenges and connects their microscale behavior to their macroscopic response. By tracking the local strain energy during compression, we reveal a transition from granular-like to continuous-like material. Mean contact geometry is shown to vary linearly with the packing fraction, which is supported by a mean field approximation. We also validate a theoretical framework which describes the compaction from a local view. Our experimental framework provides insights into the granular micromechanisms and opens perspectives for rheological analysis of highly deformable grain assemblies in various fields ranging from biology to engineering.