Over the many years I've taken daily doses of medications, I've developed some of my own tried and true methods to get the stuff down the hatch.
These ideas aren't exactly a "spoonful of sugar" like your grandmother used to say, but here's what works for me in regards to taking pills of all sizes:
By far the simplest trick is to take a sip of whatever you're drinking before you put the pills in your mouth, and then swallow with a second sip. This gets your throat into the swallowing action and you're less likely to gag.
If you have a pill that tastes bad on your tongue, separate it from the others and then swallow it last. Place it on the very back part of your tongue and use a flavored drink to help wash away the taste. Sucking on a small piece of chocolate immediately after helps, too (a few M&M's perhaps?)
Try taking your pills with milk (unless your medications specifically say 'avoid dairy'- be sure to read the labels!) or another thicker drink to 'cushion' the feel of them in your mouth.
LOOK at the pills (in your hand) that you are about to take, count them and visualize taking them before sticking them into your mouth. Sometimes eying the medication connects your brain to what you're doing and makes swallowing easier.
Use applesauce or cottage cheese to lump the pills into one big spoonful (do not open/crush/break pills) to swallow together. The texture of the food will mask the size/shape of the pills.
Take pills in more than one swallow. Even if I only have two pills to take (which is rare!) I swallow them separately. My regular pills usually take 2-3 swallows to down.
It might be a no-brainer to some, but sit up straight when taking pills. Trying to swallow while half-laying down creates more opportunity to gag or have them fall out of your hand or mouth.
Knowing you need daily medications to live is a jagged little pill of a concept - but taking them doesn't have to be. Instead of dreading your medication time and the after-effects, try as hard as you can to think about making yourself healthy. It's work (being healthy) but its worth it!