A tool-in-tool device driven by a single power spindle performs multiple operations on a workpiece. The device includes a first tool holder for holding a tool such as a drill, and a second tool holder surrounding mounted on the first tool holder. The second tool holder may hold a second tool such as clamp for clamping the drill to the workpiece, a guide bushing for guiding the drill and a chip breaker for breaking workpiece chips generated by a drilling operation. Multiple interchangeable bushings allow matching the bushing to the size of the drill.