An executive who hosted a dinner for Japanese clients gave everyone silver letter openers and was mystified when all of them were left behind. But what happened is no mystery to Hilka Klinkenberg.

“In Japan—and in parts of Europe and Latin America—you don’t give something sharp because the subliminal message is the severing of the relationship,” says Klinkenberg, a consultant on global manners and protocol, whose company, Etiquette International, was subsequently hired by the executive’s company.

Such faux pas are not limited to cross-border misunderstandings. Klinkenberg was consulting elsewhere when an executive assistant told her that her company’s C.E.O. needed a primer on gift giving.

“[The C.E.O.] had given her a big box of chocolates but knew that she was diabetic,” Klinkenberg says. “Somehow, he just didn’t put two and two together.”

While hanging Christmas stockings over cubicles and spinning dreidels during board meetings are not advisable, gift giving during the holidays is alive and well in the workplace. According to Promotional Products Association International, a trade group, corporations spent more than $4.5 billion on gifts to clients and employees in 2006. While plenty of that money is spent on fruit arrangements, more companies are beginning to think outside of the basket. Some hire gift consultants who steer them clear of gift minefields (jewelry, fragrances, and—apparently this isn’t a no-brainer for everyone—lingerie) and help them devise structured gift-giving programs.

“Some gifts that just get the job done, like pens and wine, are uninspired but adequate,” says Melinda Crews, a consultant whose M. Crews & Company has designed gift programs for companies including Hertz, Virgin Atlantic, and UBS. “But you’re missing an opportunity to show that you’ve thought about it.”

Whether buying for the boss, subordinates, or clients, Crews says that before you go shopping for a gift, you should “take five minutes to sit down and think about what the relationship is between [you] and the recipient.”

Buying for affluent C.E.O.’s can be particularly mind-boggling, of course, because “it’s not like they can’t purchase anything they want,” says Crews. “You don’t want to just walk down the street and go into a store—you have to find something that is more meaningful.”

A rising star who is buying for the boss might be tempted toward the extravagant, “but sometimes putting a financial limit on yourself makes you more creative on what the gift would be,” Crews said. Plus, nobody likes a kiss-up. “You don’t want to look like you’re going out of the way to curry favor with your boss.”

When asked to help choose gifts for executives, she begins researching the recipients’ interests and tastes.

“I liken it to due diligence for a deal,” Crews says. “It’s 90 percent thought and 10 percent actualization.”

A few years ago, an international copier company wanted a holiday gift for one of its senior executives—a golf fanatic—so Crews arranged for a personal tour of the U.S.G.A. Golf House and Museum in Far Hills, New Jersey. The location also houses a golf-equipment-testing facility, and since Crews had done some research and knew that the executive was mathematically inclined, she arranged for him to view firsthand how golf balls were tested in the lab. (While the executive was thrilled with the gift, he wound up being unable to take the tour because of a last-minute business trip.)