Would You Snitch on Your Boss?

Let's say your boss he/she is decorated, many years seniority, highly regarded/recognized...and this person asked you to conceal an activity upper management wouldn't approve of.  Would you do it?

(True story)  About eight years ago (the hotel is no longer in existance now) my immediate boss swore me to secrecy about his actions.  There was a woman whom he liked and made a hotel key to see her during bedtime hours uninvited (although she flirted with him previously).  I was newly hired, so if I did tell, in all likelyhood I would lose my job.

It's unfair of the boss to bring an employee in on their secrets. I would absolutely tattle if it meant losing my job once the secret was out and I knew of it. Many companies have some sort of "Tell Us" program where employees can speak freely and anonymously. In a situation where someone's privacy was being invaded, I would so tell.

Lips, your friend imo has every right to go to HR with her claim.  She doesn't have to take that treatment.
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"You worked at a hotel and the boss made a key to enter a room, uninvited?

Am I reading this correctly?

Was the woman an employee?  If so, why would she be sleeping at work? And why in the world would a boss divulge this info to an  employee?

I'm kind of lost on the specifics of the situation."--Gabby

The woman in question was a stripper (actually quite famous locally--think Nikki Newman from the Young and the Restless.  This young lady was thin, blonde and glamorous, came in a limousine (by her rich manfriend?) when she was in town and all of the managers on staff were alerted upon her arrival. (She made $1000+ a night).  She was also very arrogant and was known to leave $400,$500 unpaid bills ordering food & drinks.

My boss was crazy about her and figured this was as close as he was going to get to a "Nikki Newman", and since she flirted with him, this was his big chance.

The thing is Lips, my boss was never invited to her room, (either way would be a violation of hotel staff rules 1)uninvited--breaking and entering or 2) fraternizing with hotel guests (if invited).  A lawsuit from her/her rich manfriend would not only hurt the hotel,it would affect the chain than managed the hotel and others.  If he had her consent, why did he swear me to secrecy about his actions?

She sounds like a spoiled brat.  Sorry, but I hate people who leave unpaid tabs.

That being said, your boss had NO right to enter her room. 

With the facts you gave me, NO, I wouldn't have told.  I wouldn't risk my job on someone like her.  Sounds snotty, but those who indulge themselves without paying really gripe me.

Hey buddy whats the verdict? Did you go to upper management with it. This wasn't a woman knitting baby booties in the hotel room. Still unclear was she unaware he was there?

Funny you ask how it turned out Liquorman.  As insurance, he had some minor things reported on me that put me at "Second strike" with upper management, so my word didn't mean much--if all else, he could say I was stealing from the cash register (which was dishonest).  I quit soonafter (on the theft accusation, not the stripper secret.)  Roughly a month later, I noticed in the local paper they were taking applications/resumes for my bosses' position & word on the street was he was fired.

Was she aware he was there, unknown (he said she was aware he was watching her sleep.)  Personally, I didn't believe anything he said after he swore me to secrecy.

what goes around comes around lol 

I mean how would I go about telling upper management that my boss was going upstairs in the middle of the night to see some woman that he more or less doesn't know that happens to be a stripper?  (I'm having a difficult time explaining it to all of you now.)

I wouldn't have told on him. In fact, I never did that although I might have been better of if I did.