In a method of making an entry hole for implanting a retrograde humeral nail across a fracture in a humerus comprises the initial step of providing a pin placement guide having a base with a bone contact surface and a guide portion attached to the base. A guide bore with a guide axis extends through the guide portion and the bone contact portion of the base. The pin placement guide is clamped on the humerus so that the guide axis is at a relatively small angle of less than 20.degree. with respect to the bone axis of the humerus, and the bone contact surface is substantially aligned with the bone axis. Next, a guide pin with a tip is inserted through the guide bore. A guide hole is bored into the bone along the guide axis with the guide pin. Next, the clamp and pin placement guide are removed. Finally, the guide hole is reamed to enlarge it into an entry hole that is at an angle with respect to the bone axis equal or less than that of the guide axis. The retrograde humeral nail is then inserted through the entry hole in a conventional manner.