There's gadgets like this which some people find useful:
https://www.amazon.com/OralFlo-RC-02-Oralflo-Pill-Swallowing/dp/B000NJJ3C4
If you Google pill swallowing techniques there's also lots of ideas, but it's been a while since I looked into it so not sure which sites are great. Generally they advice practising starting with cake sprinkles and working your way up. There's a way to do it with a water bottle that mimics the pill swallowing cup or some people find wrapping the pill in marshmallow or bread helpful
This might work
https://www.amazon.com/OralFlo-RC-01-Oralflo-Pill-Swallowing/dp/B000NJJ3C4
Best wishes to you and your family
No personal experience, but I've heard good things about this product: http://www.amazon.com/OralFlo-RC-02-Oralflo-Pill-Swallowing/dp/B000NJJ3C4
Maybe ask the pharmacist if it can be broken or crushed? If not, maybe try this : http://www.amazon.com/OralFlo-RC-02-Oralflo-Pill-Swallowing/dp/B000NJJ3C4/ref=sr_1_1?ie=UTF8&qid=1386069668&sr=8-1&keywords=pill+cup
In the recent VLOG, TB said that he had a lot of problems with swallowing pills. My girlfriend has the same problem so I looked this stuff for her a while ago.
There are two solutions that I found:
1) Oralflo Pill Swallowing Cup - Which you can get at Amazon for a pretty cheap price, which should help a lot. Link: http://www.amazon.com/OralFlo-RC-02-Oralflo-Pill-Swallowing/dp/B000NJJ3C4
2) There's a site called 'Headstart', which is basically the Israeli Kickstarter, and some pharmacist is now trying to fund a device for swallowing pills as well (I just want to point out that I have NO relations to the guy, I just found out his project recently by chance). The device is already ready and can be bought from him for a very cheap price. It's in Hebrew, but I can help with that if needed. Link: http://www.headstart.co.il/project.aspx?id=10099
I'm not sure any of this is helpful, but maybe TB for some reason didn't search for this and it might help him.
Feel better TB!