Very carefully. I take it that you are not dealing with a premade guard. I start out with something to use as a blank and lay out the center lines in both the center of the stock length wise and to the center of where I want the tang to pass through on the other plane. You really need calipers to measure the width and thickness of the tang where the guard will be located. Layout fluid comes in real handy for laying out the line. Then I use a counter bore bit to start the holes. I use one that has a diameter that is smaller than the thickness of the tang where it passes through the stock and carefully drill on the center line of the long axis just inside the limits of the tang hole that I want. You only want to use the narrow part of the bit, not the thick part to do a counter bore. The reason for that is the narrow part of the bit is very short, and thus, very ridged. These are just starter holes. If the tang is wide enough to drill a hole in the middle where the two center lines cross you can do that too. You then go to a long bit that is the same size or just a tad smaller than the width of the tang and finish drilling through the stock. The reason that you drill the pilot holes with the counter bore bit is that it keeps the longer bits from wandering. Just keep the pressure on the second bit light until it enlarges the hole left from the counter bore bit.
Next the real fun starts. Get some needle files and connect the holes being careful to stay withing the lines laid out for the hole. Then square the hole with a flat needle file while checking the fit often and filing a little between checks. When I have the tang sitting snugly in the hole right where I want it. I use a jig to hold the guard in place and soldier it, though some people use JB Weld.
There are other ways to do this. One maker who lives north of me remembers that he's a blacksmith too and hot punches the hole then enlarges it to fit the tang. Making a small hot punch for myself is one of those things that I keep meaning to get around to some day.
Others go whole hog and get a milling machine to cut the slot. It's faster and more precise than the method that I use but a heck of a lot more expensive too.
A trick that you can use to correct for a loose fit is to work around the hole with pin driver to upset the steel. Once the guard blank is snug again you will have to sand down the face of the blank to remove the marks from the pin driver.
I'll have to admit that putting a guard on a knife is not on the list if the 10 things that I like to do while building a knife
Doug