Hi there,
I never really had a problem with swallowing pills until I was prescribed a medication with the oddest shaped pill (like three triangles connected to each other) which was also quite large. I learned through trial and error to get it down by first, taking a big swig of water, swallowing it, then placing the pill as far down my tongue as I possibly can . Then calmly take another drink of water. I think it's really important to relax when doing this. It should go down without problems. This might prove to be difficult if you have a sensitive gag reflex, but if your careful to not touch the back of your throat, it might work for you. I know I can feel my taste buds when placing the pill in my throat.Maybe have someone with you the first few times you try it until your comfortable with the procedure. I know people can teach themselves to take pills as I helped a good friend with the same problem. She also had a sensitive gag reflex, but overcame her fear of large pills.
I also heartily agree with greengrass that you need to know which pills can be crushed.Many are meant to be taken whole for the reasons already stated in her post.
To your health,
J.