As part of the ongoing service we render to you, dear readers, from time to time we 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: the rather pressing issue of holiday gift-giving at the office. Said another way: should I be giving my boss a holiday gift this year?
the dilemma of holiday gifts at the office
We all know that offices 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 C-Suite Council, and herewith provide “expert” answers to your work-related holiday gift questions.
Please note, there are important cultural differences surrounding these matters. So if you think you know better than we do what would be best in your own situation, go with what you know.
should I be giving my boss a holiday gift this year?
Well, that depends. In most cases, yes, and what you give is highly dependent upon your situation.
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. By the way, your board members and investors should be doing the same thing for you.
If you’re in management:
Plan A:
Our C-Suite Council is unanimous on this one. The best possible gift you can give your boss if you’re in management is getting together with your peers and pooling assets for a group gift.
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. It’s completely incidental if the boss likes the group gift. Because the real gift is that everyone on the team got together to do something nice.
Plan B:
If you’re in management and your peer group is either so dysfunctional or so far-flung that you cannot corral them into a group gift, then go to Plan B. Give the boss something extremely inexpensive, or free.
Why? Because you’ll never be able to give someone who makes twice (or more) than what you make an appropriately expensive gift.
Instead, give something that fits their emotional needs. A travel blanket or crazy airplane socks for the road warrior. Perhaps a book you know they’ve been meaning to read, or a tee expressing a wry sense of humor or an in-joke. The goal is something that they’ll love but that costs very little (if you’re spending more than $25, you’re spending too much).
Failing that, you can write a heartfelt note about what you admire and respect about your boss, and thank her for everything she’s done for you this year. Which costs nothing at all – a kind note is free! If it’s sincere, your note will be highly valued. Make it short, very specific and authentic. No sucking up, though – smart bosses can see right through that, and it will not be appreciated.
what about other office gifts?
If you’re in management:
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 in management and also the fun type:
You could launch 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.
But what if your team is too big for dinner or secret santa?
Too many direct reports (or too many different locations) 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.
These notes offered specific and personal thanks and congratulations for the year’s accomplishments. People loved those notes (we still have all of ours). We know it takes time to write all those notes, but it’s totally worth it. Even if people don’t personally tell you so, they treasure these testaments to your personal knowledge of and appreciation for their hard work and contributions.
what about my assistant?
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 giving a wrapped present. But also give them the financial means to get what they really want. (By the way, this methodology works really well with teenagers, too).
how about my clients?
If you are sending a gift to your clients (and possibly also your prospects), our C-Suite Council strongly recommends that you make it as personal as possible. Sending every client the exact 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, we NEVER want a gift of food. During the holiday season, we are metering out our caloric intake in tiny increments with no margin for error, in a usually futile attempt to not gain weight. But of course, food is exactly what some other people may want. We love books (which of course, some people don’t).
For sure, you should do some intelligence-gathering and ask the client’s assistant to give you some idea of what the person might want (if you don’t know them well enough to know already).
We think the best bet is to send a sincere and personal hand-written note to each of your clients. 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. And if you’ve learned enough about them to know if they’d appreciate a nice bottle of champagne, or the latest book on political history, or a gift certificate to a spa, then gift that along with the note. That’s a combination they’ll remember.
OK, that’s it! You’ve got our best response to the question should I be giving my boss a holiday gift this year?
And you’re ready to face the holiday workplace minefield with a smile.
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You got this, boss. We’ll see you at the office party.
