Originally Posted by Onganju

I think the biggest obstacle is coming to a point where you need to train while being conscious of the fact that you have to utilize it more. This is where havign a training partner becomes real effective. While being able to just drill repetition on a heavy bag will go a long way, if you have skilled partner with a set of focus mitts/thai pads who goes out of their way to constantly feed angles and targets that require you to use your off hand it becomes more engrained in a way that becomes "combat applicable." Just hitting a static target will help you with form, but you need a sparring partner to help train timing and rythm.

This can also help with grappling also. After rolling enough with my buds, it was very comforting to know that I can catch them with my left arm when going for a choke or armbar opposite my strong side. After a while, they started defending against my stronger arm and I needed to start going to the off hand to catch them. Once I got them worried about both sides, my game got bigger because I had many more options added to my set-ups and attacks.