A business etiquette expert tells how to take the awkwardness out of playing Santa at the office.
FORTUNE — Dear Annie: This is my first holiday season with my current employer — I’m in my first “real” job after college — so I hope this isn’t a dumb question, but what is generally expected in big companies regarding gifts to bosses and coworkers? I interned all last year at a small family-owned firm where everyone knew everyone else really well, and we all had fun giving each other little Christmas and Hanukkah presents. But everything at my new job is much more formal, and I don’t want to get this wrong. Should I give my boss a gift, or will that look like I’m kissing up? What about peers? Are there rules for this? — Santa’s Stand-In
Dear Stand-In: It’s not a dumb question at all. “Proper etiquette around gift-giving at the office is a snake pit for most people, because there’s always the potential for making some sort of faux pas that will come back and haunt you later — or at least, you fear it might,” says Vicky Oliver, a personal branding coach and author of 301 Smart Answers to Tough Business Etiquette Questions. “For instance, let’s say your officemate has a little box with a bow on it on her desk. What if it’s for you and you didn’t get her anything? What if it isn’t for you? Should you still give her something? If so, how much should you spend?”
In hopes of dodging such dilemmas, it’s customary at many companies for colleagues who aren’t also personal friends to wish each other “Happy holidays” and leave it at that. With any luck, your employer is one of them. “Gift-giving is one of those things that varies a lot from one corporate culture to another,” says Oliver. “So your best bet is to ask someone you trust who’s been there for a couple of years what, if anything, people usually do. Then just follow their lead.”
In general, Oliver adds, “you don’t need to give gifts to all of your coworkers unless you work in an office of five or fewer people, where leaving one person out would hurt his or her feelings. However, if you have a colleague who has been particularly helpful to you this year, a card expressing thanks and a small gift is entirely appropriate, even if you don’t do the same for others. Just be tactful and discreet about it.”
You might find that standard practice at your company is for teams or departments to chip in on one gift for the boss, which Oliver says is a widespread tradition that costs each person some small amount of cash and keeps coworkers from one-upping each other. (It also precludes the appearance of, as you say, kissing up). But if that isn’t how they do it at your company, Oliver offers five suggestions for blunder-free gift-giving — whether to your boss or to anyone else.
1. Don’t overspend. “The rule of thumb for office gifts is that they be inexpensive,” says Oliver. “It’s poor etiquette to spend, say, $50 on a silk scarf for a coworker, because chances are she’ll have bought you a little box of candy and be embarrassed.” Oliver recommends keeping each gift at a $20 limit: “Think about a gift card, a cookbook, a bottle of wine, a gourmet food item, a potted flower, or a two-drink voucher at a local watering hole.”
2. Thoughtfulness counts. “Avoid giving the same gift to everyone in the office,” Oliver advises. “It’s okay for companies to do that — send the same gift basket to every client, for example — but for individuals, no.” Instead, pick a gift based on what you know the recipient likes. “The point is to show you put some thought into it,” she adds. “If you’re aware that a coworker is trying to lose 10 pounds, don’t give them a box of chocolates.”
3. Keep a couple of “anybody gifts” handy. Just in case someone shows up in your cubicle bearing a gift you weren’t expecting, says Oliver, it’s a nice idea to have one or two already-wrapped goodies stashed in your desk — for instance, a paperback bestseller, or a pair of designer-inspired sunglasses you picked up at a discount store. If you don’t get around to buying (or wrapping) these, though, don’t worry about it: “It’s perfectly fine to reciprocate by taking the person out to lunch.”
4. Don’t try to be funny. What one person thinks is hilarious, a colleague might see as in dubious taste, or just silly (or both). So play it safe and don’t go there.
5. Always give to helpers and service staffers. These include support staff such as receptionists and assistants in your immediate area, as well as “other support staff, including the mailroom person, perhaps a frequent messenger you know by name, the night or weekend cleaning person, and anyone else who makes your everyday life easier and more pleasant,” says Oliver.
In many offices, someone takes up a collection for these staffers on behalf of the whole group. “Always give cash in a nice card,” Oliver says. “These people often make minimum wage or close to it, and a $20 bill goes a lot further than a pair of gloves.”
And speaking of appreciation, even if you work in a culture where it isn’t customary to exchange gifts at all, you can’t go wrong by sending holiday cards with short, handwritten thanks to colleagues whose work over the past year has inspired you, or made your job easier or more fun. “People love to get these,” Oliver observes. “Often, they’d rather get a sincere ‘thank you’ than any other present you could give them.”
Talkback: Do people exchange holiday gifts where you work? What’s the best — or the worst — present you ever got from a coworker? Leave a comment below.