Q: I work at a company where raises and bonuses haven’t been given out in five years. This past year, the owner bought a Bentley and a home in the Caribbean. Morale is at an all-time low. How can I tell the owner in a subtle way that the Christmas card she sent to employees featuring a photo of her family lounging on a Caribbean beach was tacky? – “Ginger”

A: J.T.: We can only imagine the “boss on the beach” remarks going around the office. But how can you communicate that it was tacky? I fear that criticizing her wealth-flaunting might just be job suicide. It’s like telling someone that their significant other is cheating on them – even if you’re right, you’re wrong because you’ll always be associated with the awful news. And in this case, you’d be associated with moral judgment, and your boss might not want a censorious eye on the payroll. What does that leave? An anonymous note comes to mind, but that might cause the boss to be mistrustful of the entire staff or blame someone innocent.

Dale: I once taped a newspaper cartoon about tyrannical bosses to the door of our company’s owner. I liked the boss, and thought he’d find it funny. But within the hour, he huffs into my office, slaps the cartoon down and says furiously: “I know who did this! It had to be George, and I’ve had enough of him!” So I had to confess, and he wouldn’t talk to me for days. But back to the beach photo. You and Ginger have picked up the wrong end of the bat. You should be thankful that the boss didn’t send a picture taken beside the Motel 6 pool. Be glad you have a rich boss. The issue now is how to get some of the profits. You won’t get there by begging for crumbs from the big table. Instead, go to the boss with a plan – something like: “I think we could do X dollars in sales if the team shared in the profits. Would it help you if I looked into it?”

J.T.: What I like about that approach is that you don’t have to convert the boss to high ideals; instead, you make the boss an offer, one where she benefits, too.

Dale: It’s no accident that the richest man in America helped so many others become rich that they have a name: Microsoft Millionaires. You might not be able to get your boss to be less tacky, Ginger, but you probably can help her see that generosity could result in having more money to flaunt.