What to Give Your Boss as a Holiday Gift

Office gift exchange can be a nightmare, especially when it’s your boss.  Believe me, I know, it’s as hard to give as it is to receive.  The ritual is uncomfortable, filled with anxiety and trepidation.  Most everyone wishes it would just go away — let work be work, gifts are for the kids, right?

Let me share with you a personal anecdote, and then an unlikely bit of advice about what I think your current boss really wants from you on the gift list.  Then I will share an idea about how to make the holidays even more satisfying with one of my personal favorite “work things” to do this time of year.

Somewhere along the way I acquired more than a passing interest in wine, and as people with a passion for something have a tendency to do, I talk about it from time to time.  I will try not to bore you with the details, but when we lived in Northern California we ventured to Napa and Sonoma on weekend drives, and that is where I began to discover the creative process behind wine is like art, poetry, and storytelling blended metaphysically with supply chain economics, agriculture, and marketing.  With my obsession around the marriage of technology and media (show + business + bits + capital), the real world metaphor of wine was a perfect diversion for me, a subject of endless study.  The more I studied every aspect of the vineyard, the more I talked about it.

Oh, those frightened employees!  How pretentious!  How intimidating!  Now we have to spend a week’s pay on a bottle just to avoid a CLM (Career Limiting Move) every holiday season.  Nightmare on Goldstein Street!

Nope, not at all.  Never asked for a bottle, never expected a bottle, and when I would get one, if it was pricey, I would donate the value of the bottle to charity and nicely advise the giver to please lighten the wallet load in the future.

Yet whenever I did get a bottle as a gift from an employee, here is what I would do — I would write his or her name on the label and the date of the gift, then store it in a closet, which eventually evolved into a more formal wine cellar.  There it would sit in the dark (luckily, my chatter reinforced my predisposition for reds, which even if they don’t age well, usually hold up if stored decently).  Then, years later, on random occasions, I retrieve the bottle because I have a taste for it, almost always forgetting who gave it to me.  That’s when I look at the label, smile, enjoy the wine, and I do my very best to find an email address or phone number for the person who gave me that bottle and I get in touch — to thank them again, to tell them the wine was good (it always is), to see how their career is going, to see how their family is doing, just to reconnect.  It’s an excuse to recapture a great slice of life, and that brings the gift full circle.

Some of you reading this have received those calls or emails from me.  Some of you haven’t because I can’t find you, but most of you haven’t because the wine is still down in the cellar and you will — sooner or later, you won’t escape.  That’s what makes the gift unique.

So if someone gives you a bottle of wine, no matter the circumstances, try the same trick, and wait as long as you can before you reach for the stored bottle, let time pass, and then open that bottle as a way to remember that person, and an excuse to reconnect with them.  You will be surprised how much fun this is, how gratifying it is, and what a great sense of continuity it brings in tying together seemingly unrelated chapters of your life as your network of colleagues expands across the globe and lives their lives with all the ups and downs we all experience.

Okay, that was the anecdote, but it was for illustrative purposes only.  This post is not about wine shopping or storage.  Let me tell you now what your boss really wants most from you for the holidays:

A better relationship.

It’s the same thing your boss wants with you all year long.  It’s the same thing you want with your boss.  You don’t need a bottle of wine to get there.  A kind note will do.

Want to know another secret?  If you write your boss a kind note at the holidays solely for the purpose of improving your relationship, your boss is likely to save that note, just like a bottle of wine.  This is not about sucking up, office politics, or any other hallway chatter you are better off avoiding — if you don’t want to do it, you should not, it is not a job requirement.  Of course your boss may not be the shiniest object in the room, perhaps you even think he or she is a nasty freak who is out to get you.  That might be true, but in case you haven’t already figured it out, bosses knows they make mistakes all the time, they worry about it, they feel terribly about it, and most of them wish you didn’t think they were out to get you.  You might prefer to fill a turquoise Tiffany box with treasures you can leave on the boss’s desk to faking a kind note, and if that is the case, you should do neither.  A wrapped gift is only a token of expression, a means to outreach, so if there is no outreach, don’t bother, you’re wasting your money.  You can give a gift, you can not give a gift, honestly I don’t think it will get you off the S-List, nor will it lead you to unwarranted promotion.  Good bosses are smarter than that, and they know the rules.

The holidays are an opportunity for reflection on all fronts.  If you do use this time of reflection to build a relationship, to settle a difficult matter of the past, to ask a candid question about how you could be doing better, to tell your boss what you like about your job, that could be a path to bonding with lasting value — and by lasting, I mean years beyond the job you currently have.  I stay in touch with some employees for decades — not all of them, but surely the ones with whom I built a relationship.  That door is open for you now, you just have to decide if you want to walk through it and have a conversation.  Hierarchies are one directional, no question about that.  Relationships cut two ways.  Hierarchies are determined by corporations with documents on record in the HR department.  Relationships are determined by people, no files at all.

This leads to my final point: What about that former boss, the one you never did give a bottle of wine or a note?  Surprise that person!  Email them as if you opened the bottle of wine and saw his or her name on it.  Tell that old boss what you are doing, how’s the spouse, the kids, the dog, the job, the retirement, the untenable new boss with whom you wish you could have a relationship.  We used to do this with Holiday Cards, and some people still do with photos of the family sitting under a palm tree on their summer vacation in Tahiti.  No one has time to write all those notes anymore — we are a busy, wired, short attention span theater crowd that communicates more efficiently on Facebook, Twitter, and in blog comments.  So just pick one each year, and see what’s there.  You will be surprised.

Whether your long-ago boss or your current one, believe me, he or she doesn’t want you to spend your hard-earned money on them.  They do want to know how you are doing.  That is a gift that is as priceless as it is ageless.

Celebrate the day, keep peace in your heart, wish for a better world and do your best to make it so!


One thought on “What to Give Your Boss as a Holiday Gift

  1. Love this post. Totally agree, we don’t give people enough positive feedback up, across and down (although that one we see as our job and focus on it a bit more). I am so impressed with your blog articles and read all of them. I appreciate and respect you more now I know more about you and your philosophical views that you choose to share.
    So my addition would be, that we should take the time to share a little more about ourselves with those that we spend so much time and effort with so they don’t have to guess if we want a gift or not and what it should be, they would know what really matters to us, which is their happiness and satisfaction with their jobs and boss :) BTW, I don’t have your email now you are not at shop.com!!!


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