Thoughts on drilling holes thru good paint?

2 hands on the drill , low speed , sharp/new bit and I like to use a tiny bit to create a dimple -1/16 or smaller in the surface of the paint but I just drilled 4 in the inner fender without the pilot dimple last week .do not drill you pilot hole all the way through the shape of the bit point works better when the angles are the same at penetration .If you have ever had a bit jamb in the hole this is why and a stuck bit leads to chipping .