How to rotate to maintain direction

I have this screwdriver rig and I want the base to rotate to maintain contact between the screwdriver on the rig and the player’s hand. I drew this a diagram to better show what i’m trying to do, in this context the black box is the screw driver and the red diamond is the hand. I tried using the find look at rotation node but that doesn’t seem to give the correct rotation. It seems to always return around 90 degrees and only changing small amounts, despite moving my hand completely around the screwdriver. Is there a better way to do this?