My feeling has been that if you intend to teach someone how to stickfight, get them used to having something coming at them from day one. I usually don't get to drills until I've had a chance to see how they do with some simple knife fighting. Put on the fencing mask, light gloves and light wooden dowels (for beginners) or the newer aluminum knifes that have a bit of an edge and a point (not for beginners) and see how they handle themselves as "empty cups". I am more interested in how they behave while on the verge of an epiphany than if their swing or technique is perfect on day one. It really helps you get a sense of their essence.
Knife fighting/sparring is nice and simple compared to stickfighting - and a lot less damaging too. With first timers, I will always don on a heavier than normal glove because it takes a few moments - sometimes a few sessions - for the person to feel comfortable hitting me. Consequently, I have to let them hit me uncontested for a period of time. With more advanced players, it usually only takes an exchange or two and they're hooked.
When it comes to drills for a Roof block, Umbrella etc, I will have the fighters pick any rattan stick they want and I use a flexible padded stick. We both wear light head gear and gloves are optional. I get to swing at them as hard as I want and they get to block and close and maybe get in a thrust or takedown. The object is to get in as clean as possible. The lessons that most get is
1) I swing pretty hard
2) It's a lot harder to close unscathed than most thought.
3) It's much easier to close behind a roof block if you've actually put it to the test a few times.
The flip side to this is when I let the fighters be the hitter. They then get an appreciation of just how much power it takes to keep a determined opponent off them. My advice to them is if your opponent isn't ready to flinch or get out of the way when you start your power shot, you're not hitting hard enough.
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