For softer wood, drill the pilot hole slightly smaller than the screw's minor diameter. Also, be sure to enlarge the pilot hole enough to make a larger, clearance hole. This larger hole allows the screw to pull the 2 boards together. The clearance hole should be at least as large as the screw's major diameter On trim however, this is an issue. There is a tool for that. It is called a nail set. A nail set is a small tool with a semi flat point to allow you do tap the head of finish nails below the surface of your trim. You want to take care to just drive the nail far enough so that any filler you use to hide the nail hole will be easy to finish Joe Truini: One technique is to take a finishing nail—the same size nail you're using to attach the molding—and snip the head off using a pair of nippers or lineman pliers, like these here. Then simply use the nail as the pilot drill bit. Chuck it into a drill, and use the nail to drill the pilot hole. Just remember not to apply too much pressure, or you might bend the nail Pilot holes guarantee that your screw won't break off and your wood won't crack. For most hardwoods, the pilot hole should be at least as large as the screw's minor diameter. If the screw has deep threads, or the wood is very hard, the pilot hole should be another 1/64-in. larger than the minor diameter. For softer woods, the pilot hole. It's relatively easy to drive concrete nails into green concrete, but if you have to nail into fully cured concrete, you may need to drill a pilot hole for each nail. The masonry bit you use to drill the hole should have a diameter at least an eighth-inch smaller than the nail shank -- if it's any larger, the nail won't hold here