If you like your work to look good and/or have a professional appearance, here’s another idea which removes the hassle of counter-sinking. Drill the counter-sink first!
It’s a technique I’ve used for many C/S situations, and which provides a near perfect looking result whether or not the C/S screw is in position.
It assumes however, that you are both unperturbed by altering the tip of a twist drill AND that you are capable of sharpening drills by hand.
Select a drill which is only just bigger than the head diameter of the C/S screw. Sometimes there are drills which sit in the drill stand that hardly ever get used. Even if the selected drill has to be used in a hurry later, it will still work.
Instead of the usual 30 degrees, grind the tip of the drill to 45 degrees to match the underside of the screw head. A further improvement which I alway use is `pointing’ the drill tip on the corner of the grinding wheel, effectively thinning the drill web. Some practice is needed to get this right, but it’s worth the effort. Go easy with backing off (lip relief angle), a reduced angle goes towards improving the finish. When you get the geometry right, it’s almost impossible for the drill to chatter.
There’s more good news. It’s easier to see the drill tip, you can use normal drilling speeds, and you can still drill into virtually any normal workshop material.
On the down side (there has to be one!?), a little care is now needed with a normal 30 degree drill when starting to drill the clearance hole for the screw body.
By the way, if I want a quick means of de-burring a hole, a large drill given the 90 degree treatment comes in very handy too.
Another tip if you happen to be drilling brass, is to remove the sharp cutting edges of the drill so that it has a negative `top’ rake. Because of the `nature’ of brass, this reduces the tendency for the drill to snatch or dig in.