Usually on HF & goblets I will drill a little smaller then my finished hole size to a little less then my finished depth. Try to use forstners when ever possible. With nasty hard end grain on goblets I will cut with a bigger forstner to a depth were the out side of the cup start to taper back to the stem then switch to a smaller bit to get a deeper hole. I fell like I am cheating when I do it this way, but until my skills improve drilling will be my method of choice.