The Leader’s Gift-Giving Guide – Holiday Gifts Everyone Can Use


Holiday Gifts for the Office Crowd

‘tis the season to think about all the people who helped you get where you are today. Whether you are a senior leader or an up-and-coming manager, it’s important for you to thank those who make an impact in your work life. And by “thank,” I mean give them something of value.

It’s amazing what the phrases “thank you” and “I appreciate what you do” can mean to your administrative assistant throughout the average workday. Over the years, the AskTheManager editors have come to realize that our fathers’ were right: you can attract more flies with honey than you can with vinegar. And by “sugar,” they meant something of value.

Interestingly, I personally cringe when I receive a gift from anyone at work. I’m not sure why, but I just don’t like getting “boss” gifts from subordinates or anything from a peer. Of course, I am always very, very outwardly appreciative. Additionally, most gifts I’ve ever received from my supervisors were just pure crap (save for the travel alarm my boss gave me last year; I’ve used it at least twice a week since then). 

While I do enjoy the occasional gift from vendors and suppliers, I mostly receive thoughtless baskets of fruit and snacks that I put in the break room for the huddled masses to enjoy. This seems to kill two birds with one stone: as I can both receive and give with the same gift. (Careful, I’m not talking about re-gifting.)

What to get that Special Administrative Assistant?

The best gift a leader can give their admin is the daily affirmation that they really and truly “rock.” Telling them that they are “awesome,” that you “appreciate their commitment,” and that “you could not function without them” are the keys to keeping most assistants happy and healthy. If you do this daily, you are truly an enlightened leader and ahead of nearly all others.

Of course, come this time of year, your hyper-performing admin is expecting something really great. Disappoint them and you could be forced to live with a passive-aggressive psychopath for the next 365 days.

Here are our suggestions for great gifts for your administrative assistant:

  • Gift Cards – you can never, ever go wrong with the right gift card. If your admin is living at or below the poverty line, however, be careful to avoid the completely unusable $25 Morton’s Steakhouse gift card. Instead, opt for something in the $200 range from the always welcome
  • Wine or Liquor – if you’re certain they can appreciate great wine or liquor, then you’re probably okay going in this direction. If not, avoid buying the 2002 Opus One for someone who enjoys Riunite on Ice (that’s nice). If you know they love wine, but they may not be a true connoisseur, perhaps you want to give them the best wine opener ever invented. In this case, has some great reviews. To see these, follow this link.

  • Gag gifts – What are you, thirteen? The last thing your hardworking admin wants or needs is some piece of crap gag gift. They won’t “get it,” okay? Even if they do, they won’t appreciate receiving some bobbing head ostrich-thingy that appears to go on forever. Avoid, at all costs, any urge to go for the exotic or gag gift for your direct reports.
  • Crystal Vase – Household accessories, especially a crystal vase or similar display piece could be something your admin will not only treasure, but also remember – provided you give some measure of thought to the gift. 
  • Over the Top – Amazingly we are willing to spend thousands on a single business trip that yields nothing and just $50 a year on the person who may mean the most to our success, our administrative assistant. Why not go crazy in 2008 and drop $1,000 on a big screen HDTV or Movado Watch.

What Should You Get Your Boss?

In short, nothing. While it’s true that the right gift could earn you brownie points, the wrong gift can indelibly brand you as a sycophant. If you’re sure your boss loves “something,” then it might make sense to find the right gift. Here are some suggestions:

  • Is Your Boss a Wine Lover? – If so, a case of 2004 Silver Oak is the bomb. Don’t have $900 to drop on the guy? The Vertical Rabbit corkscrew from Metrokane might be just as well-received (and it will last longer).
  • Sports Fan? – If your boss follows a specific sports team or grew up watching a specific player, the right collectible could put you in their thoughts on a daily basis. An autographed card, ball or other memento – especially if it doesn’t appear contrived – might be just the ticket. 
  • Not Sure? – You can never go wrong with a personalized holiday card to your superiors, especially if you have children. I’ve always included my bosses on my Christmas card mailing list. My holiday cards prominently feature my three (hungry-looking) children on the front. I’m careful not to put my ugly mug on the card, or to have too many amenities in the background for fear my boss might realize I’m overpaid.

What about the Office Gift Exchange?

The dreaded office gift exchange – why couldn’t I be sick that day?

There is almost nothing as painful as trying to look happy when you peel back the wrapping of an office party exchange gift only to reveal stinky potpourri or a book claiming to detail the “Best Bathroom Trivia” of all time. (I’m really okay never knowing that WD-40 stands for “water displacement, 40th attempt.”)

There are only two answers for the question “what is the proper gift to get someone for the office gift exchange:” Liquor or Gift Card.

  • Liquor – Company policy permitting, a bottle of Single Malt or Bombay Safire is the perfect gift for anyone on this list. Besides, if they hate it, they can always trade with the guy who got some crappy lavender potpourri.
  • Gift Card – Everyone, and I mean everyone, likes getting a gift card from a store or restaurant they’re likely to patronize. Not sure? Get them an Amex or Visa Gift Card – though be careful of fees.

Customer Gifts Must Rock…

I’ve been on both the giving and receiving end of customer gifts, and I can tell you that (when the gifts are right) it’s much better to receive than to give.

However, before you send a thing to any of your customers, make sure you know a little something about them. For example, I only golf when forced by business circumstances, though I invariably receive at least three dozen monogrammed golf balls every holiday season. By mid-January I won’t be able to recall who sent balls and who sent nothing. Clearly, those who sent nothing are ahead of those who sent golf balls.

If you don’t know what makes your customer tick, you’re better off keeping any gifts you might send for yourself.

Start today to discover what makes them tick, what they love, and why they do what they do. Chances are you’ll find out that they really appreciate their kids, as I do, and that tickets to The Nutcracker for their family will go ten times further than a $500 bottle of wine. Here are a few tips:

  • Egomaniacs love anything that makes them feel important, so something expensive or something with their name on it works here.
  • Gift baskets might be okay for someone who isn’t yet a customer. If you’re trying to get your name in front of someone cheaply, a $75 gift basket should do the trick.
  • Liquor or wine – If you go this route, make sure you spend the cash. There is nothing worse than a bad bottle of wine (except, maybe, for bad shrimp). Instead of selecting the decent $20 Coppola for ten of your customers, get your best customer an Opus One and send the others a nice card.
  • Gift Card – what, are you crazy? This is tantamount to bribery. Avoid cash and cash equivalents when you consider gifts to customers.

When it comes to holiday gift giving, your mom was right: it’s the thought that counts. When you look at your list this year, be sure to put the proper thought to each gift and remember that most humans will reward those who most appreciate them. Happy Holidays.