Become a Gift-Giving Guru Choosing the right gift is harder than it seems--and choosing the wrong one could cost you.

Last December, Jennifer Finke, having thoroughly enjoyed working for a client, decided to send her a gift. Finke, 32, who owns JF Communications, a public relations and corporate writing firm in Denver, had a goal similar to any entrepreneur. She wanted to let her client know that it had been wonderful to work with her--and, of course, subtly hint that the door was wide open to work on any future projects.

So Finke mulled over a few traditional ideas before deciding on something new and fresh: a customized bobblehead. She sent an online toy company a photo of her client, and they made a bobblehead with the client's head on it. The cost; about $100. A few weeks later, well after the gift had arrived, Finke hadn't heard anything from her client. She e-mailed her to see if she had received the gift. The client replied with a curt, "Yes, thanks."

And that was it. No gushing about what a creative, thoughtful gift it had been. The e-mail was the virtual equivalent of chirping crickets.

Scenarios like this, of course, unfold all the time. After all, this is that rare time when business meets pleasure, when entrepreneurs intertwine themselves in a period in people's lives that is often deeply personal and frequently rooted in religion, not to mention childhood nostalgia and myth (think Santa Claus). And all of this is frequently going on under the influence of alcohol. No wonder so many business owners get into trouble.

Getting caught in a holiday blunder is also a numbers game. As Jean Kelley, a veteran business consultant based in Tulsa, Okla., who frequently deals with business etiquette issues, puts it, "Everybody from every culture is celebrating something around this time, and we've been doing that a couple thousand years now, so when you get people together who are celebrating their culture bad things can happen."

So if you're wondering how not to be the guy with the lampshade on his head or the gal who wishes she hadn't sent a bobblehead, analyze your holiday plans very carefully. Being thoughtful requires way more thought than you can imagine.

The less alcohol served, the better
Not everyone will agree with this sentiment, and we don't blame you if you're thinking, "What the heck!?" But keep in mind what Kelley says, "When people drink, it sort of blots out their forebrain thinking--a lot of things will happen that wouldn't normally." Kelley recalls being at a holiday party when the president of a company stood up and, slurring his words, said, "There isn't anybody in this company who is a better manager than ."

Then he blurted out that person's name.

The president may have made one manager's day at the party but offended all of the other managers. If you feel like you should provide alcohol at your party, then make sure your party isn't at the office--and definitely not during working hours. That sends the wrong message, says Larry Rice, the dean of academic affairs at Johnson & Wales University. People these days don't expect alcohol in the workplace--unless, of course, you work at a brewery.

But drinking after company hours is perfectly appropriate, especially if you're away from the office, says Rice. In that case, if you want to play it safe, it's best to go with wine--and even better if you have a professional doing the pouring. "Once you accept the responsibility of serving alcohol, accept the responsibility of serving it responsibly," says Rice.

And if you drink, Kelley recommends not partaking in more than one drink an hour, to keep you from saying or doing something--well--stupid.

Remember thy office commandment: Keep religion out of the holidays
Yes, if you grew up worshipping Santa Claus and tying popcorn strings around the tree, it might be a bummer not to refer to your party as a "Christmas party." But as everyone should be perfectly aware by now, there are plenty of people who don't celebrate Christmas.

Rob Basso, 37, of Payroll Advantage, based in New York City, was reminded of that a few years ago when he noticed that one of his employees never came to his company's Christmas party. He asked her about it and learned she was a Jehovah's Witness, and a tenet of that faith is to eschew holidays, even birthdays. But once Basso renamed the office bash a "holiday party," and once everyone began a holiday gift exchange instead of a Christmas gift exchange, she came, and a good time was had by all.

One size doesn't fit all
We all know that one-size-doesn't-fit-all is a rule for clothing, but it's also a guideline you'd do well to consider before giving any gift to an employee, client or vendor. Basso, who works with a lot of business owners, says he knows entrepreneurs who have given out chocolate as a gift--which sounds wonderful.

That is, chocolate is wonderful unless your employee is watching his weight, or worse is diabetic. That's not to say you shouldn't or can't give chocolate as a gift, but it's smart not to fall back on those automatic presents that seem perfectly safe. Think about it first. The larger the group of people you're sending gifts to, the more thought you should give to any possible problems that could arise from your present.

If you're sending perishables, include instructions
Felecia Hatcher, president of Feverish Ice Cream Truck based in Los Angeles, decided last year to send her own product to a client, which didn't seem like a big deal at the time. After all, a normal business might mess up sending ice cream, but she knew what she was doing. Indeed, Hatcher packed her ice cream in dry ice, and her gift arrived at her client's office without any problems.

Only Hatcher forgot one thing. "I didn't label the boxes to say that they must be kept cold, and the client was out of the office all day," recalls Hatcher, 26. "To make a long story short, the package was placed on her desk until she got back the next day, and when she returned, our ice cream was--as she described it--a gourmet milkshake."

Make sure everyone's accounted for
It's nice to know that even an expert on hospitality like Dr. Rice isn't impervious to making etiquette mistakes during the holidays. Rice says that once he and his wife prepared baskets of homemade chocolate for all the people in his office. He was so caught up in the excitement of the holidays that he didn't notice an employee was out sick; when he noticed that an untouched basket remained at the end of the day, he concluded that he made too much. He gave the basket to the cleaning lady and then heard an earful from the employee the next day.

"It was held against me for a while," admits Rice, "but now it's become a running joke."

Make sure any gift you give is in keeping with your company's theme
Alexandra Drane, 38, co-founder of the Eliza Corporation, a healthcare communications company in Beverly, Massachusetts, sent out Wicked Whoopies, large, locally made confections of chocolate and cream, to some key clients and contacts. "While we appreciate the gesture," shot back an e-mail from one of those key clients, "this is not in keeping with our culture of health and wellness."

Ouch. Drane quickly apologized and sent him a fruit basket instead. "This year," says Drane, "we're going with some fancy loose tea. It's healthy, it's somewhat trendy."

Everyone's tastes are different--so if at first you don't succeed, try, try again.
Marie Johnson, 48, is the president of IzzyLou Studios, a Hudson, Wisconsin, nonprofit that aims to help business leaders and educators retain what they learn. Johnson used to give Christmas and sometimes Thanksgiving dinners away to all of her employees as a gesture of thanks. Meaning, she gave everyone not just a Christmas turkey or ham, but additional food as well, so employees could celebrate with their own friends and family.

But it was eventually brought to her attention that she had staff members who were vegetarians and were naturally quite upset that year after year, they were being given what amounted to a meat lover's paradise.

The following year, Johnson just gave everyone money.

But right away, Johnson got grief because the gifts would be taxed. "I heard complaints, and that wasn't the atmosphere I was trying to create with the gift," says Johnson.

So the next year, Johnson gave everyone gift cards to a grocery store in close proximity to their business. But that didn't go over well, either.

"I picked a high-end quality store, thinking it would be a great treat with the homemade baked goods and a butcher that cuts things to order, thus less stress for the employees at the holiday," says Johnson. "I picked that store because once a month I picked up fresh baked goods, and everyone raved about them."

But the staff wasn't happy. They felt if she had picked a store like Walmart, the money would have stretched farther. Johnson told everyone she had taken that into account and put more money on everyone's grocery store gift cards than she would have put on a Walmart gift card, but she got the message.

Now, says Johnson, "I just started having a holiday feast at work, inviting everyone to bring in a dish, and the company would furnish a few high-priced items." The staff votes on those items to avoid any more complaints. "That was the best for employees," concludes a weary Johnson, who adds that, oddly enough, she has never had a holiday gift flop with her clients.

Your Holiday Game Plan
You have two choices as the season gets close--hide in a closet until New Year's Eve, or participate in the holidays and hope for the best. If you do the latter, then follow these guidelines, and you can't go wrong. (Probably.)

• When it comes to gifts, be consistent, especially when it comes to your employees: Intentional or not, "when you give a gift, you're sending a message," says Rice. "Any individualized gift opens up so much room for error." But it's a numbers game here, too. Kelley admits that in a smaller office setting--say, one with five employees--you can get away with sending some individualized personal gifts that you can't in a company with 50 or 500 employees.
  
• Put some thought into the price of your gift or a holiday party: Much like gift-giving, when you throw a holiday party, you send a message. Provided everyone's treated the same, an expensive gift will probably go over well, whereas an expensive office party may not. That's because a party is for everyone, including the boss, and the staff may feel the boss is doing very well and not necessarily deserving of such a gala.
  
• Stay professional and don't get too personal: That doesn't mean you have to give everyone a fancy pen or briefcase. But stay away from jewelry and clothing. "It's too intimate," explains Rice. "You're sending a message to that worker's peers, even if it's subliminal. They're going to be wondering, 'Why are you giving them jewelry? Or, why are you giving them wine?' You never know what that does to the office environment and the peripheral staff. It may just be a small, subtle concern, but why make people pause like that? Everything is fine, until someone has a concern."

Look, you know your own company's vibe. If times are flush at your company and people are well-compensated, a fancy office party and luxurious gifts are going to be in tune with your culture. But if everybody's been scraping by all year, and your employees feel like they're overworked and underpaid, a party at a swank hotel may make them wonder if they're being cheated in every paycheck. A more modest party--and an added Christmas cash bonus for the employees--will likely be more appreciated.

If we're talking about a gift for a client, Kelley points out that if it's a big client that spends a lot to use your services or product, they may actually expect an expensive gift. Tickets to a Broadway play or the opera would certainly be within reason. If it's a smaller client, says Kelley, a food basket or bottle of wine would be perfectly acceptable.

Making a donation to a charity in your client's name is another option. If you do this, just make sure it's a charity your client is interested in, rather than one your business is involved in. Otherwise, your donation will come off as self-serving.

Whatever you do, here's a good rule of thumb to follow, says Kelley: "It's better to give no gift at all than a cheap gift."

But if you blow it by making a holiday blunder, it doesn't have to mean that heads will roll. Apologizing and moving on seems to work wonders. Dr. Rice's spurned employee forgave him. Alexandra Drane is still in good stead with the company that shot down her dessert gift--in fact, Drane says, "We've actually increased the amount of work we do with them since the gaffe."

Even Jennifer Finke is still occasionally in touch and has worked intermittently with the client who isn't crazy about bobbleheads. A blunder can be embarrassing and potentially costly, but entrepreneurs shouldn't beat themselves up too much when they make them, especially if it's a relatively minor matter of simply misreading what someone would like as a gift. After all, nobody's perfect, and to err is human.

Still, Finke admits, "I don't think I'll be doing that again," adding in the same breath that, this year, "I'll stick to popcorn tins and fruit baskets."

Geoff Williams is the author of C.C. Pyle's Amazing Foot Race and co-author of the upcoming book Living Well with Bad Credit.