It's not a dumb question, this is not intuitive unless you've played NBA2K before (which we both haven't it looks like).
- Tap the LB/L1 button
- Don't press any buttons yet, but find the player you want to pass to
- When you've found that player, press the button of that player
AND hold the direction of the cut you want them to move towards on the
LS
They should then move a little towards that direction.
The lead pass towards the basket, doesn't seem to work when pointing in the direction of the basket UNLESS that teammate is moving (this is the only way I've been able to see that lead pass to the basket made).