I’ve never had a problem tipping the mailman, the garbage men, the cleaning people…people like that.

You may think I’m being overly generous, but that’s the way I was raised.

I always remember my dad tipping for Christmas whoever would provide service to us during the year.

And even when it came to gifting the boss, I always thought it a nice gesture to give something to him…no matter who it was.

Brown nosing you say? I expected that, but again always thought it to be a nice gesture.

We can debate the merits of tipping the mailman etc. till the cows come home….but how about giving a little something to the boss for Christmas?

Well, I’m sure most will say “f#*% that!”

Sherri Athay, author of “Present Perfect: Unforgettable Gifts for Every Occasion,” generally advises employees not to get the boss a present. However, she says that small gifts, such as baked goods, are appropriate.

April Masini, who pens the online advice column, AskApril.com, cautions that it’s important to understand your workplace’s culture.
“If you're not sure, ask around. Some companies are very easygoing about gifting up and anything goes. Others frown on it. And still others expect it,” Masini told TODAY Money. "This kind of etiquette isn't going to be in a human resources handout. Use your social skills to figure out your company's unwritten rules.”

While the experts say skip it, or at least proceed with caution, employees also have mixed feelings about giving the boss a gift.

Susan Moon of Seattle ….“I’ve never done this or wanted to – then, my last boss was a really bad one, a bully,". "My current boss is terrific, I have more appreciation because of my immediate prior bad experience, and I’m finding myself wanting to find a small gift to 'gift up' this year.”

Most employees who were comfortable with the idea of giving the boss a gift felt it should be more of a token gift rather than a big, under-the-tree type of present.
Where employees can really start to get resentful when it comes to gifting up is when bosses seem to expect (or at least accept) large, lavish gifts.

Of course, the best gifts are priceless.

Jeff Mac of Albuquerque, N.M. says “I like to give my boss the gift of pretending to care about my job every day,”

The type of organization you work for can have a lot to do with the practice of gifting up. Those in the military, who work for the government or who are members of unions are likely to find the practice frowned upon, if not banned outright.
While some employers may enjoy or even expect gifts from their subordinates, others are uncomfortable with the idea.

Maggie Reed of Davenport, Iowa said…“From the perspective of a boss, don't buy me anything,” “I am a firm believer in the separation of boss and employee for ethical reasons."

Jody Gowdy of Maple Valley, Wash., echoed those sentiments. "I would never expect something and honestly find it uncomfortable when it has happened in years past. We give the employees something every year as a thank you for job well done. But I would say no."

If you do decide to give a present to the boss, experts have some advice on how to do it gracefully. “Make sure you keep it humble and a token of your appreciation," Masini advises. "It's inappropriate to 'one up' your boss's gift. It may make your boss feel uncomfortable.”

Masini also notes that employees should make sure any gift is in line with their salary. "If you make minimum wage, and you give your boss an Hermes scarf or a ... bottle of champagne, they're going to think they're paying you too much or you're terrible with money.”

Masini also warns employees to make sure to gift in the proper chain of command. "In other words, don't gift jump by ignoring your immediate boss, and gifting your boss's boss. Gift jumping is bad politics and will yield you in hot water.”
This year the funds are low, so there will be more discretion in who gets what from me.

And while I will temper what I’ve given in the past with present day financial realities…I still have to come to grips with the fact that I’d hate having to chase my garbage pails down the block on trash day.

So yes, in some cases, tipping isn't a bad thing?