When in a precarious situation, such as when falling lock stock and barrel when the tree is near structures etc., it takes a whole lot of nerve. The trick is to implistly trust your holding wood.
Now lets say for example a relatively straight tree sets back on the backcut. If the holding wood is only 10% or less of the total stump area, it will not fall in that direction unless subject to high winds.
Case in point: Today I was falling a 38" dbh Rock Maple that had a slight lean towards an adjacent property (open feild).
To help commit the tree over, I backed the log skidder up to the tree, climbed on the log arch, which put me 13ft. above the ground. From this position I tried to lassoo the trunk with a 10' choker, but could not get it around. So I had to choke it at only 5' above the ground.
Having done this, I drove the skidder ahead 125' under the intended direction of fall and locked the brake drum with the cable being very taught. Then I proceeded to place all the cut. Having done that I climbed on the skidder and applied 30,000# of pull. I couldn't see the tree move, but it did lift the front end of the skidder 3 ft. off the ground which weights 16,900#.
To get out of this one, I had to release the cable, which caused the tree to set back until the backcut closed.
So at this point, I had two options. I could back against the tree with the log arch of the skidder and push it over, or relocate the cable on the trunk and choke it higher, which is what I did with the help of a long stick, so the tree was choked about 7' above ground now. After repeating the winching procedure, the tree simply fell in the intended direction. The tree weighed about 18,000 lbs. I have repeated this many times in the woods over the years and have never had a tree get away on me- knock on wood.
My point to this big long disertation is two things:
1: The strength of holdingwood.
2: The mechanical advantage of leverage.
John