Should I Be Giving My Boss a Holiday Gift This Year?

As part of the ongoing service we render to you, dear readers, from time to time we here at Dandelion Chandelier will turn our attention to Thorny and Sensitive Questions We All Have.  We promise to work our personal networks relentlessly to get inside expert answers for you. And failing that, we’ll just tell you what we’d do. And hope that we don’t steer you wrong.

First up in this series: the rather pressing issue of holiday gift-giving at the office.

In all seriousness, we know that the office can be a minefield at the holidays, whether you work at a large corporation, a start-up, a family business or even a not-for-profit. There is no settled consensus on the why’s, whether’s and how’s of exchanging gifts in the workplace. Throw in the added potential awkwardness of gender – is it easier to give a gift to a boss who is the same gender as you? Or harder? – and you have the possibility of creating a hot holiday mess.

As a result, by January 1 the office can resemble a battlefield, strewn with the bodies of those who miscalculated; presents tossed aside; food gone uneaten; and tissues soaked with the tears of those whose expectations were tragically out of line with their particular workplace reality.

Oy vey!

In the spirit of getting you through the holiday season with your professional prospects enhanced (or at least undiminished), we have queried our far-flung correspondents, and herewith provide inside answers to your work-related holiday gift questions. Please note, there are important cultural differences here. So if you think you know better than we do what would be best in your own situation, you may very well be right. You’ve been warned.

If you’re the big boss:

–If you’re the Chairman and/or CEO at the top of your organization’s hierarchy, you probably either report to a board of directors, a few investors, or perhaps to no one at all. In two out of those three cases, the best “gift” you can give your boss(es) is a hand-written note of appreciation for their support throughout the year, and best wishes for the season. Extra style points if you make it truly personal to each of them. Why do this? Because everyone – even the most powerful person in your orbit – likes to feel acknowledged, especially at this time of year. BTW – they should be doing the same thing for you.

–If you’re the boss of a group of other people, at any level from CEO on down, you should definitely do something special for your direct report group. Why? Because their success is your success, and depending on your management style, they may often wonder if you realize that. We suggest that you host a proper sit-down dinner for your staff in a private room at a good restaurant within walking distance of the office. Make it easy for people to do this after a busy day at work. Be emotionally present, tell some self-deprecating stories, find out what everyone is doing for their year-end vacation, don’t check emails, and don’t skimp on the wine or the food options. Yes, you should spend your own money – not the shareholders’ money – on this meal. Extra style points if you allow everyone to bring their partner. Golden tiara for you if the entire family is invited. Yes, a celebratory toast is mandatory, so plan ahead. No free-lancing.

–If you’re the fun type, you could supplement this meal by launching a Secret Santa gift exchange among your direct report group. Have everyone pick the name of a peer out of a hat, set a spending limit, have people give their anonymous gifts a few days beforehand, and reveal their identities at dinner. You’ll learn a lot about your team, and they’ll learn a lot about each other.

–Too many direct reports to make this practical? Take a lesson from the master: as CEO of General Electric, which had 300,000 employees and a core management team of 70+, Jack Welch used to send a hand-written note at year-end every year to each senior manager; the notes offered specific and personal thanks and congratulations for the year’s accomplishments. People loved those notes. I still have all of mine. (This also works brilliantly if done on people’s birthdays, which is what another one of my great bosses did every single year that I worked for him). We know it takes time to write all those notes, but it’s totally worth it, even if people don’t personally tell you that.

If you report to the big boss (or actually to any boss):

–Having been the manager for a lot of different kinds and sizes of teams, I can say with confidence that the best possible gift you can give your boss is getting together with your peers in the direct report group and pooling assets for a group present. Why? Because every manager wants to believe that their team is so well-calibrated and collaborative that they are capable of self-organizing to make this happen. Also because a group gift wipes out issues of gender, favoritism, toadyism and other unpleasant possibilities. Added plus? You can get something really nice with all that scratch! So whatever internecine rivalries may be playing out, put them aside and show some teamwork. Having all of my direct reports get together to give me something is the gift I always hope for, and it’s completely incidental if I like whatever they decide to give me. The real gift is that they got together. Everything else is frosting on the cake. (This technique also does the trick on the boss’s birthday).

–Plan B, if your peer group is so dysfunctional or far-flung that you cannot get them to join you in a group gift, is giving the boss something extremely inexpensive, or free. See our prior post for our patented 5-step no-fail gift giving process . All of those rules apply here, but with much less fuss: you’ll never be able to give someone who makes twice (or more) than what you make a fancy and expensive present. Instead, give something that fits their emotional needs, perhaps something expressing a wry sense of humor or an in-joke, something that they’ll love but that costs very little (if you’re spending more than $25, you’re spending too much). Or – and you’ll note that this is a common refrain – write a heartfelt note about what you admire and respect about your boss. If it’s sincere, I assure you that your note will be highly valued (no sucking up, though – smart bosses can see right through that, and it will not be appreciated).

If you have an assistant, get that person something lovely and splendidly wrapped, and also send some cash their way in whatever form feels right to you (gift certificate, cash, or check). You’ll never be able to correctly discern what this person wants, so make the kind gesture of a wrapped present, but also give them the means to get what they really want. BTW – this works well with teenagers, too.

If you are sending a gift to your clients, we strongly recommend that you make it personal–sending every client the same item is a waste of money, because it’s highly unlikely that whatever the item is will be equally appreciated by all. For example, I NEVER want a gift of food – at this time of year, I am metering out my caloric intake in tiny increments with no margin for error, trying not to gain weight. But of course, food is exactly what some other people may want. I love books (which of course, some people don’t). Best bet and sure to please (yes, you’ve heard this before): send a sincere and personal hand-written note. It will stand out in the clutter of all the other “stuff” your clients are receiving (and probably re-gifting) at this time of year.

A few other tips:

–If there’s a big office party, and you’re in senior management, LEAVE EARLY. There’s zero upside to your presence there for more than about an hour, unless important clients are invited, in which case you need to stay until they leave.

–Even if you’re really good and the music is great, if we were you, we wouldn’t dance. Ever. Despite the glitter ball and dim lighting, this is actually still work, and there are definitely still boundaries (see the classic Seinfeld episode when Elaine dances at the office holiday party if you need further proof that it’s a bad idea).

–If you think you might be drinking too much, you definitely are. Stop immediately.

–When in doubt, do nothing that you would not do in front of the HR person. Or your mom.

OK, that’s it! You’re ready to face the holiday workplace minefield with a smile. You got this. We’ll see you at the office party.

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