In creating this example, I've had several errors I don't understand. If I create the hole, it appears the size of the circle on that plane doesn't matter, so I have to adjust in the hole parameters. Also in the hole "Tasks", I can't get anywhere without having a profile, though I can set it to none in the parameters later on. And I get the message that my diameter size is too large, don't know why. If I adjust Hole Cut Diameter down in parameters, it is happy. I'm guessing this is because the diameter in the Hole Tasks tab is for countersink.
Attached is the example with the plane on the top of the last pad, and the countersink on the wrong side of the body.