Most guides have a groove or relief, right where it seats on the head . drill about 75% of the size of the guide, just past the groove. Give it a sideways tap, top breaks off.
Then use driver to push guide into the port. Best way is to mount a pin that locates the guide or a fixture at proper head angle in a drill press.
Guide holes always get lines in them pushing the other way, no matter how clean you try to get them.