The First Two Drills for Pole Training — Only Joint Rotating

The first two drills for training the pole are probably the most familiar to learners, namely, lifting and pressing the pole vertically up and down very close to the body between chin and pelvis, and pushing and pulling the pole out and in on the chest level. In both cases, the pole must be kept, more or less, horizontal throughout, i.e. the head and tail of the pole are always kept in pace, so that it can deliver power in its entirety, not just partial or even self-countering.
Instinctively, one is tempted to hold the pole tight in order to manoeuvre it as a weight by lifting, pressing, pushing and pulling. Such weight-dealing skills are deemed wrestling and struggling.
The Wing Chun way is like this. Take the first drill as an example. Use joint-rotating to keep the pole travelling on the vertical pane very close to your body. There is no distinction between up and down, nor out and in; just the elbow joint being rotated (by the shoulder joint) to the back or to the front. When rotated to the back, the elbow joint rotates the wrist centre upward (if the wrist centre is below the elbow; let’s label this as “back-upward”), or downward (if it is above; label this as “back-downward”). The opposite is also true: When the elbow joint is rotated to the front, it rotates the wrist centre downward (if the wrist centre is below; label this as “front-downward”), or upward (if it is above; label this as “front-upward”).
Your focus has to change, not on the hand (holding the pole) lifting up and pressing down, but on rotating the elbow to the back or to the front. There is then no lifting or pressing force in the hand, because it does not need to cause the pole to move on its own; rather, it is “passively” being rotated by the elbow joint (via the wrist centre).
The hand, i.e. the palm and fingers, doesn’t need to tense up to lift or press. It can then turn into an adhesive surface to wrap-hold the pole.
If you can’t switch over to use the joint-rotating mechanism, probably your hand must hold for a tighter grip and thus tense up to a certain degree for lifting and pressing the pole (the heavy weight) when moving it, and you can hardly hold the pole sticky.
There is one more moment to consider: when the elbow joint and the wrist centre are approaching the same level (let’s label it as “level”), i.e. when the forearm is resting on the horizontal. This occurs when the wrist centre crosses the elbow’s level from above to below or vice versa. At this moment, the wrist centre adds its rotating to the palm (in the fist shape), and hence to the pole, to alter the fist’s head to the opposite direction (above to below, below to above). When the fist’s head is altered from downward to upward, let’s label this as “level-upward”, and from upward to downward as “level-downward”.
Now we can use the above labels to compose the pole drill movements.

When you send the pole from below (the pelvis level) to above (up to your chin), it is composed of “back-upward”, followed by “level-upward”, followed by “front-upward”. Similarly, when sending the pole from above to below, it is “back-downward”, then “level-downward”, then “front-downward”.
You will appreciate that it is not one “lifting” nor one “pressing” movement, but one move composed of, at least, three rotating movements. It is this change of paradigm that makes handling the pole effortless, not as a weight.
How about the second drill, i.e. sending the pole out (forward) and in (backward) alternately? The components are: when sending it forward, “vertical-forward” (wrist changes the fist’s direction), then “up-forward” (elbow sends the wrist); when sending it back to close to the body, “down-backward” (elbow withdraws the wrist), then “vertical-backward” (wrist changes the fist’s direction). Note that in these two movements (out and in) the wrist centre is always in the front of the elbow joint except when the pole is close to the body where the two are almost vertical. I’ll leave it to you as an exercise to figure out how these components work for this drill.
The above has depicted how it should work in the arms. Manoeuvring the pole requires much power from your body. Both the wide stance and the additional momentum from (relaxed) muscular power are crucial in this respect. Only that they are not a focus of discussion here.