If your family and wife know you sometimes sleep with men, that's not necessarily a problem. If nobody knows, that's a problem. Similarly if your wife and boss don't know you owe $50,000 to a bookie or your coke dealer, that's a liability.
Actually would be sort of interesting if your boss did know you owed a bookie $50k and they found a way to use that to make you into a triple agent...
You are missing the foremost consideration - how critical/specialised/irreplacable is this person in their role and can we just ignore the positive test instead.
If you are good enough at what you do and management like you positive tests dont seem to matter if you make the right noises about it being a one off, retesting clean etc.