Remember the cloth room works like you are generating an animation. So figure and cloth loaded in zero pose at frame 1, and then figure posed at say frome 30.  With a choreographed group its at its starting location at frame 1 and at its final location at frame 30. It will move between those two positions over the 30 frames with collisions being recalculated every frame.

 

It may sometimes be helpful to keyframe some intermediate points to guide the cloth deformation.