This paper presents the optimization of a drilling operation subject to machining constraints such as power, torque, thrust, speed and feed rate. The optimization is meant to minimize the machining time required to produce a hole. For the first time, the effects of a pilot hole are included in the formulation of the machining constraints. The optimization problem is solved by using the geometric programming technique. The dual problem is simplified based on the characteristics of the problem, and the effects of machining constraints on the machining variables are identified.