My daugher's taken medicine practically since the day she was born. Since she was two we have had struggles getting her to take her medicine. One med we open up and mix into 1-2 tsp of Trix yogurt. Two others are powders that can be mixed into water, juice, or other liquid. The one thing she absolutely hates to take--for some reason--is aspirin or Ibuprofen for a headache or cold. She's allergic to mosquito bites and was using the Claritin RediTabs, which she grew to dislike. So one day, I showed her the little white Claritin pills and asked if she thought she could get something small like that down if she swallowed it with water. She did, and has been happy as a clam ever since (she's 8). Next it was Ex-lax, then another pill, and now she takes a daily probiotic/acidouphilus capsule and hasn't complained once about taking it or having to take any medicine. I'm crossing my fingers that this continues and soon she'll be swallowing pills of all shapes and sizes and we won't have any more medicine wars.
So I'd say, my advice is to start with something really, really small--even smaller than a tic-tac, like the size of a Claritin--so that it can't get stuck. Once she realizes she can get it down and it "wasn't any big deal" and it didn't get stuck, she'll get her courage up and will try bigger and bigger sizes and then Presto! she's taking pills like a pro.
That's my next agenda; to get my daughter to take the capsule I'm currently putting into yogurt so we can cut that part out of the medicine equation.
I remember the very first pill I ever had to actually swallow (my Mom would crush aspirin pills and other meds and put it in grape jelly). I was 12 and had come down with walking pneumonia. My Dad didn't have hospital insurance, so after receiving one of those big penicillin shots in the tush I was at home on complete bedrest. And I had to take one of those horse pills. Three times a day. You know, the kind the parent can barely swallow, and they've been swallowing pills forever? There was no way around taking the med, and it was a bugger for me to learn how to swallow that big su----. So I definitely encourage all children to learn to swallow pills as early as possible.
Good luck.