This is a thought that occured to me on my way to classes today; sharing it for feedback.
Omega appears before you, and after presenting an arbitrary proof that it is, in fact, a completely trustworthy superintelligence of the caliber needed to play these kinds of games, presents you with a choice between two boxes. These boxes do not contain money, they contain information. One box is white and contains a true fact that you do not currently know; the other is black and contains false information that you do not currently believe. Omega advises you that the the true fact is not misleading in any way (ie: not a fact that will cause you to make incorrect assumptions and lower the accuracy of your probability estimates), and is fully supported with enough evidence to both prove to you that it is true, and enable you to independently verify its truth for yourself within a month. The false information is demonstrably false, and is something that you would disbelieve if presented outright, but if you open the box to discover it, a machine inside the box will reprogram your mind such that you will believe it completely, thus leading you to believe other related falsehoods, as you rationalize away discrepancies.
Omega further advises that, within those constraints, the true fact is one that has been optimized to inflict upon you the maximum amount of long-term disutility for a fact in its class, should you now become aware of it, and the false information has been optimized to provide you with the maximum amount of long-term utility for a belief in its class, should you now begin to believe it over the truth. You are required to choose one of the boxes; if you refuse to do so, Omega will kill you outright and try again on another Everett branch. Which box do you choose, and why?
(This example is obviously hypothetical, but for a simple and practical case, consider the use of amnesia-inducing drugs to selectively eliminate traumatic memories; it would be more accurate to still have those memories, taking the time and effort to come to terms with the trauma... but present much greater utility to be without them, and thus without the trauma altogether. Obviously related to the valley of bad rationality, but since there clearly exist most optimal lies and least optimal truths, it'd be useful to know which categories of facts are generally hazardous, and whether or not there are categories of lies which are generally helpful.)
Well, yes, I would. Of course, it's not like he could actually say to me "your boss secretly burns puppies -- do you want to know this or not?" But if he said something like "your boss has a dark and disturbing secret which might concern you; we won't get in trouble just for talking about it, but he won't take kindly to criticism -- do you want me to tell you?", then yeah, I would definitely want to know. The boss is already burning puppies, so it's not like the first-level harm is any worse just because I know about it. Maybe I decide I can't work for someone like that, maybe not, but I'm glad that I know not to leave him alone with my puppies.
Now of course, this doesn't mean it's of prime importance to go around hunting for people's dark secrets. It's rarely necessary to know these things about someone to make good decisions on a day-to-day basis, the investigation is rarely worth the cost (both in terms of the effort required and the potential blow-ups from getting caught snooping around in the wrong places), and I care independently about not violating people's privacy. But if you stipulate a situation where I could somehow learn something in a way that skips over these concerns, then sure, give me the dark secret!
Knowing the dark secret will produce resentment for your boss. That resentment is likely to make it harder for you to get work done. If you see him with a big smile in the morning you won't think: "He seems like a nice guy because he's smilling" but "Is he so happy because he burned puppies yesterday?"