In my career as a wage slave, I learned to never ask a lawyer for permission, as the answer was invariably "No" (unless one of the C-suiters asked, then the lawyer would bend over backwards to say "yes.").
But if my risk manifested, I was on the gibbet. Ask forgiveness, but don't expect mercy, if you really screw the pooch.
I totally got yeses all the time, or don't worry about it, but generally when it had to do with are we allowed to do this under GDPR or similar things.
There are different ways to ask.
"Can I do X" - yeah that's likely gonna get a no if there's any ambiguity or question about it.
"The VP wants me to do X, what do I need to know" - probably a much more nuanced response. "Someone could make an argument that xyz violates abc, but there's also a counterargument that in this case..." (And put this question writing since it should (a) be privileged anyway - though you should check with legal first re: how they want you to indicate that, if at all and (b) it adds some paper trail if you need to escalate or if the decision is made to do something that later blows up.)