When grass gets really tall quite a few things are working against you.
Firstly as already mentioned, the grass gets laid down flat and if long enough does not stand up again till the cutting section of the blade has passed so the blade just lays it down again.
Then their is the draught created by the blades.
It is strongest on the discharge side and weakest on the left side.
Also the higher the deck the weaker the draught.
Then there is the circulating mass of the cut grass itself that can push the uncut grass flat.
Three ways to overcome it.
1) heel the deck so the back is a lot lower than the front.
When you do this the blades cut better but all 3 cut at quite a different height so you end up with a wave type of level.
If this is only being done to cut catch up on really tall lawn it won;t matter because you can relevel the deck latter on
2) mow a lot slower
3) mow backwards