We know that,
Pressure = Force/Area
P = F/A
So pressure is inversely proportional to area. As area increases, pressure decreases and vice versa.
In this case, when a man stands on a cushion, the area in contact with the cushion is less than the contact area when the man lies down on it. So the pressure when he stands on it is more than the pressure when he lies down. Hence, depressions larger when he stands.