As electronic devices and products are being miniaturized, Printed Wiring Boards (PWBs) within them are also being miniaturized. Therefore, drilling conditions for small and high density holes have become more difficult to decide. We focused on drilling conditions recommended in drill catalogs and attempted to find out the knowledge that experts of drilling use to decide drilling conditions. In this paper, we focused on web thickness, one of the drill parameters, and qualitative variables written in the catalogs. The results clarified the importance of web thickness in drilling conditions and meaning of qualitative variables.