Drilling system (10) that better uses the power curve of modern machine tools. The drill system (10) uses a two-step drill, utilizing IC inserts (50) to perform the major hole diameter cutting, and a central drilling system (70). In examples, the IC inserts (50) can be set in a drill head (30) in a single or double effective configuration. A central drilling system (70) cuts the remaining minor diameter portion of the hole, and is configured to see less cutting surface footage, due to its position from the rotating center of the tool. The central drilling system (70) may include a "self-centering" geometry, such that the drill head (30) of the tool will be guided throughout the depth of the hole. The drill system (10) allows for a large diameter deep hole that remains straight throughout to be drilled at higher speed and lighter feed rates thus offering a more productive tool that takes advantage of the power curves and lower thrust capabilities of modern machine tools.