The Ultimate Holiday Gift Buying Guide for Your Boss, Colleagues, Customers, and Staff

Holiday Cheer.jpg

It’s about this time of year when you realize, as I usually do, that you haven’t yet figured out what you are getting your colleagues for Christmas. Worse yet, your staff is about to go on vacation, and you’ve got a boss that is nearly impossible to shop for. And customers. Oh, what should you get your most loyal customers?

Buying gifts for your children or family can be difficult enough, but we tend to have a pulse on their wants and needs. Despite working closely with our business associates and customers, we often find it difficult to purchase meaningful gifts. When it finally comes time to buy, we don’t want to send the wrong impression or spend too much or too little money.

Like Santa’s reindeer in headlights, we freeze and skate by until our holiday vacation, hoping the new year is far enough away to diminish the memory of defeat.

But not this year.

This year, we’re going all out. This year we’re going to buy meaningful, memorable gifts for the people in our business lives that matter. Let’s get started.

Share this post with someone who may need a little gift-giving help this holiday season :-)...

Gift Buying Principles

With this gift buying guide, we’re going to break down some overarching gift-buying principles. Principles that apply to your boss, your customers, your staff, and your colleagues. Principles that will prevent you from making an embarrassing mistake or sending the wrong impression.

With those principles in mind, we’ll give you some ideas to kick off your shopping with a dash, giving everyone you work with a token of appreciation and a bit of holiday cheer.

It’s Not About You

Buying a gift is not about you, it’s about them. It’s about making the receiver feel your appreciation for what they do for your company, for you, and for others in your business life. Showing appreciation isn’t complicated, but it does take practice.

Start by paying attention to what your receiver talks about. Their interests will give you some great ideas of what they might like in a gift. When buying a gift, look for one that they will appreciate. Something that will make their life more productive, more entertaining, or more meaningful in some small way.  

Keep it Personal, Keep it Professional

So much of our lives are spent attempting to separate the personal from the professional. But when it comes to gift giving in a business environment, unless you’re taking part in a white elephant gift exchange, your gift needs to provide meaning and show appreciation. Find something that tells your receiver that you’ve thought about what they like while taking care to find them something that is appropriate for work.

See it From Their Perspective

Take care to look at the gift from their point of view. How will the receiver interpret your gift? If they search for an underlying message (as most everyone will do), what will they find? Buying a book for your boss called “Be a Better Leader” for example, may not be the best idea.

As they say in gift-giving, it’s the thought that counts. Just be sure to make that thought a quality one instead of buying the first thing that comes to mind.

Pick the Perfect Price Point

Given your position as a gift-giver, and the position of your gift-receiver, be sure to choose a gift that reflects an appropriate price. Spending $1,000 on your boss as a part-time employee that makes  $15k a year is going to look a lot like bribery. On the other hand, if you are one of Donald Trump’s Vice Presidents, you’re going to want to spend all of that on something unique, high end, and reflective of the high salary that he is likely paying you.

Don’t Obligate Them

Some gifts can be eaten, others sit on a desk, and then there are those that follow a person around all the time (think iPhone case, for example).

When choosing a gift, take care not to pick something they’ll feel obligated to use in your presence. No matter how much thought you put into your gift, there’s a chance they won’t like it, already have it, or just don’t want it. Buying them a monogrammed iphone case covered in bling may make them feel like they have to use it. Or, if they don’t, it may make them feel guilty for not having it on them when you’re around.

What Are You Waiting For?

Get your gift now! If you find something that fits all these principles, get it.

You are already running up against the clock. In the future, you don’t want to waste time keeping lists for people or trying to remember that fleeting idea you had while walking through the aisles at Target (believe me, I’ve tried, and it doesn’t work).

Many folks take a full two weeks of vacation between Christmas and New Years. You’ve got to buy, ship (if online), receive, wrap, and give your gift before then. Do it when you can, as soon as you can.

Now For Some Ideas

What follows are additional principles and a few good gift buying ideas (and bad ones) for your boss, your colleagues, your customers, and your staff. Jump to the section you need help with immediately, but don't forget the others!

Check out our Modern da Vinci Pinterest Board, "For the Holidays" for some neat gifts we came across while researching this article (this is not an ad, and we make no money from showing you these gifts... we think they're just good ideas).

For the Boss

Buying a gift for your boss can be extremely complicated. How much should I spend? What should I buy? When should I give it? Should I watch him open it? Adhering to the principles above can make things more straightforward however.

Keep in mind, the reason for buying your boss a gift is to show thanks and appreciation for the work he does for your company, your coworkers, and you.

To be clear, your gift is not:

  1. Intended to make you look better in his eyes.
  2. Something to hold above your coworkers heads. They may not give your boss a gift, and they shouldn’t feel sorry for not doing so. It’s not a competition, and rest assured someone else will show you up if you make it one.
  3. Meant to get you that promotion, make good on a recent mistake, or anything else that essentially amounts to bribery.

If you get them a gift, it’s to show them your appreciation. Don’t turn it into something it’s not.

With that in mind, don’t expect anything in return. The last thing you want to do is stand eagerly by as they open their gift. Treat your boss’s time as valuable by leaving it with their admin or on their desk. The card you leave with it (you did sign a card, right?) will tell them who it’s from, and they’ll get to open it at their leisure.

Finally, though it’s the gesture that matters the most, be sure to keep these additional things in mind when buying:

  1. Think small, think practical.
  2. Take care when buying their gift not to send unintended messages. Your boss may be sensitive to how he or she is perceived in the office. Well intentioned gifts that are poorly interpreted don’t go over well.

So what are some gift ideas that adhere to these principles?

  1. A sharp looking pen is practical, functional, yet can carry an air of mystique and class.
  2. A nice whiskey, scotch, or bottle of wine can be appreciated by nearly anyone. Even if your boss doesn’t drink, they likely have a liquor cabinet for company and will appreciate being able to share a bottle with their friends and family.
  3. A Bluetooth hands-free car phone is another practical gift idea for anyone who enjoys tech toys.
  4. A coffee/tea set for the avid hot beverage drinker is always appreciated. They may even go so far as to keep it on their desk for use during the workweek.

Bad ideas that don’t adhere to these principles?

  1. A gift certificate – Don’t just take the money they’re giving you and give it back in the form of a gift certificate. If they wanted to eat at Applebee's, they’d just eat there. Give it a bit more thought and find something they’ll truly appreciate.
  2. A business book of any kind – This assumes they need to know something about business they don’t know and may not be interpreted kindly. Proceed at your own risk if you go against this advice.
  3. A watch – Again, let’s not send the wrong message about their timeliness. Bosses are busy and are likely the worst offenders when it comes to being late for meetings. Additionally, watches can be a bit overly personal and hard to find the right balance between price and bling. It’s best to let their husband or wife give them this one.

For a Colleague

I use the word colleague here for a reason. Namely to keep in mind, you don’t have to buy a gift for every one of your coworkers. Some of the people we work with make a bigger impression on us than others. Some we collaborate closely with (colleagues), and others just happen to be in the same company.

When it comes to colleagues, the intention is to show your appreciation for what they do for your company, for you, and for your team. Find a gift that shows you understand them without getting too personal.

Also, take care to find the right balance between price and nice. The goal here is not to make you look good; it’s to bring them a bit of cheer. Buying them something expensive may give them feelings of guilt, make them feel small in your eyes, or make them feel as though they need to reciprocate. On the flip side, buying them something crappy will make them wonder if they’re appreciated at all.

Good Ideas

  1. Pens
  2. Desktop toys
  3. USB Charger
  4. Baked cookies from home
  5. Novelty or Gift basket (e.g., with crackers cheeses, etc.)
  6. Bluetooth speaker
  7. Nice water canteen
  8. Nice pen/stylus for their iPhone/iPad
  9. Coffee or tea set
  10. Mug with some meaningful words

Bad Ideas

  1. Kinky toys – Yeah your coworker may talk about his rambunctiousness, but you don’t have to play into it. Besides, no matter how funny you think it is, it’s not.
  2. Expensive watches – Going right along with the first principle, a watch may be a bit too personal and may be interpreted as far too expensive making them feel guilty or beneath you, potentially causing resentment.
  3. Getaways – You’re not their boss, so don’t send them on a vacation. If they want do that, they will manage it themselves. If their boss wants your colleague to have a getaway with his family, it’s more appropriate for him to send them than you.

For Your Staff

Over the years, I have had many great managers give me gifts that left a meaningful and lasting impression. Not all of them were for the holidays, but they could easily have been. These gifts showed me how much they appreciate my work, and how much they cared about my time outside of work.

One such gift was a trip for my wife and me – a weekend in Chicago. He put us up in a nice hotel for a weekend, paid for our dinners, and gave us a small gift certificate to use at a local spa. This gift was big, but it came after an exceptionally long few months of working and traveling and was an extremely welcome retreat. My loyalty as an employee skyrocketed and it’s still a memory my wife and I talk about to this day.

A gift to the staff. One that we enjoyed for years to come!

A gift to the staff. One that we enjoyed for years to come!

Another memorable gift was a Foosball table for the office. Granted, it wasn’t a gift only for me, but it was something we all loved and used and appreciated having during those long work nights.

If these ideas aren’t resonating, there are other ways to show your employees appreciation. Here are a few:

  1. Give them the gift of knowledge with a book, training seminar, webinar, or online course. This can be related to their job, but it doesn’t have to be. You’ll want to be careful not to cross the line of making this gift a “mandatory” learning experience; this is a gift of appreciation after all. But if the book or training course is something they will genuinely benefit from and appreciate at this job or their next, it could be a good idea. Especially if you allow them time to read or attend outside of regular work hours while still getting paid.
  2. Give them the gift of time. Employees give their time to your company to drive business; give a little bit of it back. Like my hotel stay in Chicago, this was time for my family and me to connect, have fun, and make memories. Other gift ideas of time can be as simple as a morning holiday party followed by an afternoon off. Your employees will come back recharged and ready to give it their all after an unexpected long weekend.
  3. The gift of charity cannot be understated. Years back, we threw the idea of a White Elephant and Secret Santa gift exchange out the window, turning our sights towards the local children’s hospital. Instead of giving $20 gifts to each other, we threw the same amount into a pot and spent a few hours one afternoon buying gifts on Amazon together. Our entire team was jazzed, excited, and feeling great about being able to provide a nice Christmas for kids in need.

Finally, here are a few other ideas that your employees may love:

  1. Pens. Not a disposable, but a nice pen that they’ll keep with them for years.
  2. Desktop toys are always a hit, especially in an office full of cubicles. Look at for some great ideas in this category. Remote control drones and USB foam rocket launchers for the office can make for a fun afternoon.
  3. Certificates to a local attraction such as sporting events, museums, zoos, etc. Just make sure you give them enough tickets to share with their friends and family.
  4. Noise canceling headphones
  5. USB power packs… one with enough juice to get them a full charge on their phone or tablet, and preferably one with a bit of style.
  6. A subscription to a virtual assistant. Set it up for them, collect the numbers and email addresses, and write in their card an explanation of how they can use it. At first, they won’t be sure how or when to call. It won’t take long though and they’ll be calling their virtual assistant to schedule appointments, do Internet research, buy birthday gifts for their friends and family, and perform many other time-saving activities. AskSunday and TimeSvr are good ones I’ve used to great effect.


Let’s face it, without customers, you wouldn’t have a business. Customers are your driving force. They are the people for whom you spend your waking hours away from home trying to help. Whether one customer is a hassle and another is a friend, showing your customers appreciation for their relationship with you and your business is a nice gesture during the holidays.

When buying your client a gift, keep your goal in mind: You’re thanking them for their business and building loyalty with them in the future. It’s OK to send company-branded goodies, but don’t go overboard. You want them focusing on your gift, your relationship, and your appreciation of them… not your brand.

One last gotcha: Take care (especially with government and government contractors) to understand gift giving and receiving laws, regulations, or company policies. It doesn’t hurt to ask an administrative assistant what gifts your receiver can accept. Here is a summary of rules for government employees.

Finally, some ideas:

  1. Gift baskets full of popcorn, cheeses, meats, and other treats are always a hit.
  2. High-quality puzzles or desk toys. Make sure they’re unique enough to be a conversation starters.
  3. Is there something you know about your customer? Buy them something that shows you are listening and care. A former colleague of mine once took his client, an angling fanatic, on a fishing trip for a weekend. His customer told me about it years later… it had still left an impression on him.

What not to get:

  1. Gift cards - Your customer gives your company money. Don't give it back to them in a different form. That's just awkward. Not to mention it shows you put minimal thought into it.
  2. Discounts - Remember, your gift is for a person, not their company. You are trying to show a single person your appreciation. While a discount on your product may seem nice, it doesn't really tell them anything other than "we'd like more of your business." Let your company's marketing team send out the discounts; you can pick something more personal.

We hope this guide gives you some things to think about before buying your holiday gifts for the office, and a few ideas to boot. Check out the Modern da Vinci Pinterest Gift Ideas page for some great pics and links to neat gifts ideas we found while researching this post.

If you have any gifts you’ve given or received that are particularly memorable, please tell us about them in the comments below. Everyone could use a helping hand with gift ideas, and yours may be the most useful one!