Due to its high versatility and scalability, manual grinding is an important and widely used technology in production for rework, repair, deburring, and finishing of large or unique parts. To make the process more interactive and reliable, manual grinding needs to incorporate “skill-based design,” which models a person-based system and can go significantly beyond the considerations of traditional human factors and ergonomics to encompass both processing parameters (e.g., feed rate, tool path, applied forces, material removal rate (MRR)), and machined surface quality (e.g., surface roughness). This study quantitatively analyzes the characteristics of complex techniques involved in manual operations. A series of experiments have been conducted using subjects of different levels of skill, while analyzing their visual gaze, cutting force, tool path, and workpiece quality. Analysis of variance (ANOVA) and multivariate regression analysis were performed and showed that the unique behavior of the operator affects the process performance measures of specific energy consumption and MRR. In the future, these findings can be used to predict product quality and instruct new practitioners.