As most who see Chi-Sao and even many who have actually done Chi Sao have already said it is a sensitivity exercise. I agree with that but the problem as I see it that really doesnt explain much. Chi Sao is an exercise use to help the practitioners learn:
Control of pressure, Drawing; this is used to diminish the opponents strength to the point where you are stronger. By drawing his arms out from his body he becomes weaker and vulnerable to losing his structure. You control his energy as you let your body fade away from him. This draws his arms and his center of gravity and you can then redirect his movement. Chi Sao practice helps train the moving of the entire structure. You learn to feel the pressure and to fade or to turn the structure to redirect the opponents energy. Chi Sao helps train the short lever principles where you use bone, joint and tendon strength opposed to muscle.
The short lever principles are directed from the ankles, knees, hips, shoulders, elbows, and wrists. This is all performed by the turning of the body as a unit by the switching of the feet. This will provide you with incredible power and mechanical strength. The training of Chi Sao helps reinforce what is taught in Sil Lum Tao and Chum Kil. The proper use of body structure, mechanical advantages, sensitivity, and applying energies all the while keeping control of your center of gravity and manipulating the opponents under the dynamics of movement created by your opponent.
A key factor in Chi Sao training is in your structure. Pressure is exerted from the body structure and not through the arms. In this way, the arms can be firm without being tense, relaxed without being flimsy. By not causing muscle contraction in the arms you remove any rebound. You also learn not to grow tense under the opponents pressure. In addition to proper body structure, you must also know proper tool structure and how to turn on and off certain muscles and joints. All of this (and many other things) is crucial. The training of Chi Sao helps train the body to release tension within the body and arms thereby not allowing the opponent to have a handle to move or control your structure. By this I mean you learn to keep your limbs stiff but soft and supple so that if the opponent were to lop (grab) your arm there would be no stiffness in the arm to hold on to. Your arm would suddenly become as soft and flexible as a piece of twine or string.
Chi Sao teaches how to maintain the facing principle. This helps assure that both arms and hands would be able to use equally.
Immovable Elbow Principle. The elbow must be maintained on or close to your centerline, and should never be positioned less than one fist length from your body. If your elbow gives, your structure is destroyed.
Structure Softening. Soften and concave the chest so that you are all shoulders, back, and forearms. This allows structural strength and firmer grounding while reducing tension in the body. It keeps your mid-body at further reach from your opponent while, at the same time, naturally extending your reach to him. The soft curvature of the body is used for setting up gaps that you may need for exercising powerful mechanical advantages in the use of your tools. Most important, it helps to remove the unnecessary tension in your own body while creating a tension and shock in your opponent.
Locking down of the shoulder. Be aware that to raise it your structure will be weakened. This is not only important while jamming and trapping, but even so in striking. Lock down the shoulders so that your structure will be powerfully unitized, rather than weakly disjointed. Locking down the shoulder does not mean tightening up the muscles. It simply means sealing it snugly into the joint so that the arm and body are connected. By locking down the shoulder you actually reduce muscle tension.
Ball Principle. If you were to roll around on a big ball, you would be rolling on multiple planes of movement. You can go under, over, around on either side and in either direction, or at any one of 360 degrees of direction, or push straight through. Learn to use this to your mechanical advantages. For instance, you might lift or push down the opponents arms or elbows to break down and move his structure, as found in the Sil Lum Tao form.
Hip Action. The hip is used similar to a bow, flexing, building, and releasing tension. A fundamental power source provided by the proper structure. Its the kind of thing that you dont see and most dont know about but be assured its there!
Tactile Sensitivity. This is what most say Chi Sao is all about. The only way to learn this correctly is to learn it from a good instructor, hands on. Learn to became one with the opponent. Feel the opponent and learn to blend your center of gravity with theirs. Tactile sensitivity also teaches how to use the full arm as a tool. Often times you will be in a position to trap or jam down your opponent by using your upper forearm while, at the same instant, freeing both of your hands. This is the Third Hand Principle.
Needless to say, this list does not include all of the principles and mechanics reinforced by good Chi Sao training such as rooting, slipping, poling, vectoring, plyometrics, joint selection, jing, simplicity, and much more. It is really simple if you understand all the complexity of details. Unfortunately most do not.
That is why to learn chi sao correctly you must learn it from someone who is very, very good. Even then, keep in mind that not everyone teaches it the same. For the most part, the tools and the rolling are pretty much the same, but the details often differ as well as the strategy. Some practitioners do it very mechanically and outstretched, while others train it close and heavy. Very few have the ability to go from one move into the next without becoming stuck and having to start over. If you find an instructor who can do this, then learn from them.
Good luck on your training
Danny T