This statement is completely nonsensical. If the person had full knowledge that the plans were illegal, why would he/she ask how far they can go before breaking the law? He/she clearly didn't know where the boundaries were.
Huh? A person can have a plan to go from 0-100 miles an hour and ask where the speedlimit is. Stories similar in a business environment are reasonably normal. "Compliance" is strictly a legal CYA department (as is anything relating to HR or "Ethics", btw.)