The purpose of this study is to propose a quantitative assessment scheme to help with surgical bone drilling training. This pilot study gathered and compared motion and force data from expert surgeons (n = 3) and novice residents (n = 6). The experiment used three-dimensional printed bone simulants of young bone (YB) and osteoporotic bone (OB), and drilling overshoot, time, and force were measured. There was no statistically significant difference in overshoot between the two groups (p = 0.217 for YB and 0.215 for OB). The results, however, show that the experts took less time (mean = 4.01 s) than the novices (mean = 9.98 s), with a statistical difference (p = 0.003 for YB and 0.0001 for OB). In addition, the expert group performed more consistently than the novices. The force analysis further revealed that experts used a higher force to drill the first cortical section and a noticeably lower force in the second cortex to control the overshoot (approximate reduction of 5.5 N). Finally, when drilling time and overshoot distance were combined, the motion data distinguished the skill gap between expert and novice drilling;​ the force data provided insight into the drilling mechanism and performance outcomes. This study lays the groundwork for a data-driven training scheme to prepare novice residents for clinical practice.