It’s the most stressful time of year–at least when it comes to gift giving. Should you give your boss a holiday gift? And if so, what is appropriate and what is the cultural norm for your office environment?

The very nature of gift giving strengthens relationships. Done right, it’s a positive move. But if done wrong, it can result in problems as favoritism and even harassment or discrimination issues can arise. Think of it as one more way to stress over the holidays.

To ease your mind when it comes to gifting your boss, here are answers to some of the most common questions about workplace gift giving.

SEE: The do’s and don’ts of giving holiday gifts to your co-workers (TechRepublic)

Do I have to buy my boss a gift?

This common question has a definitive answer: No. You do not have to buy your boss a gift. You are never obligated to give a gift to someone with power over you. It’s more likely that your boss should feel obligated to give you a gift, not vice-versa.

A recent study by Olivet Nazarene University revealed that 32% of people have purchased a gift for their boss, and women are more likely than men to purchase their employer a present.

If you do decide to buy your boss a gift, make sure you talk to HR or read the employee handbook to see if gifting a boss is allowed. In some companies, it is prohibited.

What if everyone else gives the boss an individual gift?

If you know the office culture, and that your co-workers typically give individual gifts to the boss, then take this into consideration.

However, a reasonable boss would never penalize anyone for not giving them a gift. Consider the norm for your workplace and give a gift if you deem it appropriate. But don’t feel obligated.

“The culture of an organization must not be influenced by following what everyone else is doing. An engaging environment is one where one is free to decide to gift only when one feels like. Workplaces which really care about employees don’t actually pay cognizance to who or who isn’t, or didn’t, gift. Gifts must always reflect true and genuine feelings,” said Ketan Kapoor, CEO and co-founder of Mettl.

SEE: Gift Guides for Techies (TechRepublic Flipboard magazine)

Should I chip in for a group gift?

However, if your co-workers are buying your boss a group gift and ask you to chip in, then you probably should. Sure this goes slightly against the idea of freely gifting your boss, but if this is typically how your department handles gifting the boss, the best thing is to follow their lead and contribute however much you’re comfortable giving. Typically, in most offices, $20 is considered generous per person, and $5 or $10 per person is quite acceptable for a group gift.

“When it comes to group or collaborative gifting, you must always chip in. Not being a part of such collaboration doesn’t reflect well on your part. It might inadvertently show you don’t want to be a part of a large group,” Kapoor said.

Naama Bloom, vice president of marketing at Zulily, who leads a team of more than 40 employees, said, “I’ve always come from a culture of giving down vs. giving up–the boss should be making sure the holidays are all about letting the team know management appreciates them. But, if coworkers want to celebrate their team lead–a gift that always works is one that is custom or thoughtful that speaks to the boss’s personality. It isn’t about the size or cost of the gift–the best kinds of gifts are meaningful and authentic.”

If I decide to buy a gift, how much should I spend?

How much you spend is determined by your job title, and that of the person you’re buying a gift for.

Laura Handrick, HR analyst at Fit Small Business, said, “The amount you spend on your boss depends very much on your relationship. If you are an admin buying for an executive, you might limit your gift to $20, but if you’re a VP buying for your SVP, then by all means, spend away.”

The amount you spend is a delicate balance. If you spend too much, you’ll risk offending your co-workers who will likely think you’re trying to gain favor. Remember, lavish gifts are never acceptable in the office.

Richie Frieman, author of Reply All…And Other Ways to Tank Your Career, cautions, “Don’t break the bank. Your boss knows what you make.”

What should I buy my boss?

Figuring out what to buy your boss is the toughest part. When in doubt, give a gift certificate to their favorite coffeehouse or lunch spot. Or give holiday cookies–those are always welcome. Make sure you’re aware of any dietary restrictions or allergies before giving a food gift.

A classic gift is a bottle of wine or a bottle of bourbon, but be sure that your boss indulges in the occasional glass of vino or spirits before purchasing liquor.

“The best gifts are something that speaks to your boss’s interests. Ideas include a jersey or hat of a favorite sports team, a donation to a charity your boss cares about, a nice mug with a gourmet tea for the tea drinker, or a box of fine chocolates,” said Arden Clise, president of Clise Etiquette.

Other options include a small item for their desk, such as a frame or pen holder, or an accessory for their electronic devices. Avoid gag gifts, because the risk is too high that you might offend.

Do not give a personal item such as cologne or clothes. Even flowers can be perceived as overly personal, unless it’s meant to be an arrangement for their holiday table.

What should I do if my boss buys me a gift?

If your boss buys you a gift, show your appreciation and send them a thank you note.

Even if you haven’t bought your boss a gift, and they give you something, Bloom said it’s important to remain relaxed. “Gift giving is supposed to be fun. The holiday season is always a good time to give something thoughtful to someone you care about–even if it’s a simple heartfelt, handwritten note of appreciation. It’s always in season to express thanks.”

Another option, according to Frieman, if you get a gift and don’t have one to give back is to, “Play the humble-card and just admit that you weren’t sure if you were allowed to get your boss a gift. Follow it up with not knowing the proper protocol. But I’d also bring something you baked as an offering to them–something more personal or showing you care.”

Does it matter if your boss observes a particular religion?

Most office environments celebrate the holidays without focusing on a particular religion, so you don’t have to feel obligated to give a gift particular to the holiday, whether Christmas, Hanukkah or Kwanzaa. However, giving a whimsical Festivus gift, a la “Seinfeld,” isn’t the best route, either.

“Personal beliefs aside, all leaders at all levels should build a culture of appreciation and respect. If you don’t know what religion your boss is a great way to show appreciation rather than guessing and unintentionally offending someone, goes back to giving something meaningful. The new year is always a good time to give something thoughtful to someone you care about–even if it’s a simple heartfelt, handwritten note of appreciation. It’s always in season to express thanks,” Bloom said.

Common sense plays a big role in what you purchase, if anything.

Handrick said, “If your boss practices a religion like Jehovah’s Witnesses, that eschews gift giving, or has made it clear they don’t want a gift due to their religious beliefs, then consider a homemade gift like a tin of cookies for the whole office instead. Obviously, if your boss is Jewish or Muslim, a bobblehead Santa wouldn’t be appropriate.”

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