Brendon and I have been talking about assorted ways to bore a mortise. Boring machine, gas/electric drills, drill guides and stands, etc. Boring machines fixture the drill so that it is plumb to the face of the timber, at least on sawn stock. This is handy, but requires the purchase of a machine and bits. The other common way is to just get a heavy duty drill and eyeball plumb. This works well but the bit can wander a little. This is not a big deal. The important thing is to make sure the hole starts inside the layout lines. In pic C, you can see the top two holes are plumb to the face, but the bottom has wandered a little to the right. That is ok, because the opening of the mortise is still the proper dimension, which is a rectangle like pic A. This rectangular opening is what locates the tenon. If the mortise is a little hollowed out inside, it is ok.
Post A is a through mortise, meaning the hole goes from the face to the back of the post. Even with a boring machine, the hole isn't going to come out inside the layout on the back, so you only bore halfway through. Then you flip it over and finish from the back. In pic B, you can see that the mortise is the required 6" tall on the front and back sides, but the bit may have wandered a little (dotted lines). This is all hidden inside the post, and again, is not a huge deal. With a little practice, even drilling by eye with an HD electric or gas drill, you can bore straight enough to produce excellent mortises.