Self-tapping screws have some operational peculiarities. In spite of their economical advantage that requires no prior tapping operation, a weakness of self-tapping screw-tightening operations is that screws can easily be tightened at a non-right angle, thus resulting in an improper tightening strength. Increases in outsourced workers have reduced labor costs, but the accompanying high worker fluidity means that new workers are more frequently introduced into factories. It is necessary to train new workers for self-tapping screw-tightening operations, which occupies a considerable portion of ordinary assembly works. The purpose of this study is to develop and implement a skill transfer system for the operation. This study (1) proposes a set of characteristic values for evaluating the quality of the operation and develops a device that can measure these values; (2) proposes criteria for evaluating the resultant quality of the tightening; and (3) develops a skill training system for better work performance. Firstly, sets of characteristic values for evaluating the quality of the operation, namely, torque, vertical pressure forces and horizontal vibration forces, are proposed. A device that can measure these values is developed. Secondly, criteria for evaluating the resultant quality of the tightening are identified, involving tightening torque, maximum vertical pressure and timing, vibration area during the processing and tightening period, and work angle. By using such parameters, workers with the proper aptitude can be identified. Thirdly, a skill training system for the operation is developed. It consists of screwdriver operation training and screw-tightening training with feedback information about the results of the operation. Finally, the validity of the training system is experimentally verified using new operators and actual workers.