‘Tis the season, and my favorite part of the holidays has officially begun. I have always said that gift giving is one of my hobbies, so once Halloween wraps up I hit the ground running in search of the perfect holiday gifts. I start poking around local shops, bookmarking things I find at odd hours and following the occasional internet rabbit trail, all in hopes of finding something that feels right for the people in my life.

Gifting at work has its own rhythm, though. You want something thoughtful enough to feel personal. Something that earns a smile when it’s opened and another when it’s used later. It is not always easy to strike that balance, which is why we gather inspiration each year from colleagues and friends who pay attention to what genuinely lands well.

This year’s collection grew from that spirit. You will find treats that brighten slow afternoons, experiences that create great stories and well made favorites people keep on their desks long after the decorations are packed away. My hope is that something here helps you celebrate the people who made your year a little lighter.

A Cup That Survives Your Calendar

(Recommended by Sarah Johnston)

I love gifting engraved Hydro Flask traveler tumblers. I first ordered them for new team members, then immediately bought one for myself. I use it every day and people ask about it all the time.

A solid tumbler has a way of becoming part of someone’s routine. It keeps drinks warm or cold for hours and slips easily into a cup holder or bag. Adding an engraved logo or team name makes it personal without feeling like branded swag. The engraving looks clean and subtle, which people appreciate.

Find it here: Custom Engraved Hydro Flask Traveler Tumblers.

A Snack Break with a Unique Twist

(Recommended by Stephanie Taff, Associate Director of Medical Education at Sequel Med Tech)

Food gifts make it easy to bring people together, even when everyone is spread out. Warm pretzels are always a hit and the ones from Wisconsin stand out for their flavor and simplicity. They fit the season, feel easy to enjoy and can turn a regular afternoon into something a little more fun. A box like this travels well for teams in different cities and the mix of flavors usually lands with almost everyone.

Find it here: Milwaukee Pretzel Company.

The Work Chronicles Calendar

(Recommended by Greg Roche, Founder of Retention and Rewards Partners) 

If you have someone on your team who appreciates the humor tucked into everyday work life, this calendar is an easy win. Greg Roche shared that the Work Chronicles comic hits his inbox daily and never misses, capturing corporate quirks in a way that feels a little too familiar.

A desk calendar may sound simple, yet it becomes a quiet companion through the year. People flip the page, laugh, and usually show it to whoever walks by. The clean design fits on any desk and the humor lands with a wide range of personalities, even the ones who claim they are impossible to amuse.

If you are gifting to a whole team, you can tuck a short note inside each one. A small thank you makes the calendar feel personal and turns a funny gift into something a bit more meaningful.

Find it here: The Work Chronicles Calendar.

The Perfect Combo of Salty & Sweet

(Recommended by Meg Applegate, Content Specialist and Resume Writer at Hinge Resume)

Garrett Popcorn is a true Midwestern classic, and if you have never tried the famous Garrett Mix, you are in for a treat. The caramel and cheese combo sounds questionable until you taste it, then suddenly you understand why people talk about it with so much loyalty. This is the kind of gift people open, try, then immediately pass around because it feels too good not to share.

Food gifts always bring a bit of joy to a workday. A tin can turn a meeting into something more fun or brighten the mood for remote colleagues who need a little December pick-me-up. If you want a gift that sparks conversation and a few laughs, this one never disappoints.

Find it here: Garrett Popcorn.

A Lightweight Fix for Low Battery Moments

(Recommended by Sarah Pociask)

Practical gifts tend to earn the most use, and the TAU 2 portable charger is one of those small lifesavers people appreciate more than they expect. It clips onto a keychain, gives phones and tablets a solid boost and saves anyone who has ever hunted for an outlet at the worst possible moment.

It works well for commuters, frequent travelers and anyone juggling a full day of meetings. The design is clean, the function is reliable and it shows you paid attention to real daily routines. This is not a drawer gift. It is a tiny stress reducer that goes everywhere your colleague goes.

If your team is often on the move or hopping between video calls, like most teams are, this one always hits the mark.

Find it here: The TAU 2 Portable Charger.

A Cozy Challenge That Fits Just Right

(Recommended by Susannah Baker Khayat)

Puzzles make great holiday gifts because they naturally slow the pace of a busy season. They are perfect when guests are visiting or when families want something to do together that does not involve screens.

The New York Puzzle Company offers designs that feel like little pieces of art, from vintage covers to playful illustrations. The pieces are sturdy and the finished picture always feels worth the effort. And it gives everyone something steady to focus on and invites easy conversation. It is a simple, family friendly gift that brings a lot of warmth without adding any clutter.

Find it here: The New York Puzzle Company.

A Warm Gift with that Personal Feel

(Recommended by Sarah Johnston)

I have given custom candles from an Etsy shop that lets you add funny or personal labels, and they have become one of my favorite team gifts. I once created a batch with inside jokes from our work together, and the packaging was so lovely that it felt special before the lid even came off.

Candles feel cozy during the winter, and a custom label adds just enough personality to make the gift memorable. You can include a short message, a quote your team laughs about or a scent that reminds you of a moment you shared.

It is a great choice for teams who appreciate small touches. People light candles at the end of long days to unwind, so your gift becomes part of their evening rhythm in the most comforting way.

Find it here: Custom Candles. 

A Fun Detour

(Recommended by Dominic Imwalle, Founder of DXConsulting) 

Not every great gift ends up on a desk. Some of the most memorable ones are experiences teams share together. A class, an activity or a few hours spent learning something new can create the kind of connection that feels effortless. 

If your team leans toward hands-on fun, places like “Beat the Bomb” offer a mix of problem solving and lighthearted competition. Activities like this break up routines and give people permission to laugh, move around and forget about their inbox for a minute.

Sometimes it’s easy to overlook how meaningful it can be to give time instead of a physical item. Shared experiences spark conversations that have nothing to do with deadlines and help people appreciate one another in a new way. Months later someone will mention it and the whole group lights up. For teams that enjoy being together or trying something new, an experience can feel more personal than anything wrapped in a box.

Find it here: Beat the Bomb.

A Genuine Letter and a Bottle of Wine

(Recommended by Katy Severance-Fierro, Digital Marketing Manager at Riskonnect) 

One of the most impactful and meaningful gifts a leader can give is also one of the simplest. A sincere letter, typed or handwritten, has a way of landing deeper than any quick email. It shows that someone sat down, thought about you and put those thoughts into words you can hold. 

If you want a gift that carries emotional weight without feeling heavy, this is a lovely choice. It does not require much more than sincerity. You can write about a moment you appreciated or a strength you admire and keep it short while still making an impact.

Pairing the letter with a bottle of wine or another small treat adds a bit of celebration, but the note remains the part people treasure. It is personal in a way few holiday gifts manage to be.

For Our Friends From the North: Canadian Gift Ideas

The Briefcase Coach team extends into Canada, so we know firsthand how tricky it can be to send gifts across the border during the holidays. To make things easier, our very own Christina Lee curated a collection of thoughtful Canadian favorites that highlight local makers and delicious treats.

A Practical Pick Skin Will Appreciate

Winter in Canada is no joke, which is why Coco’s Tallow is a perfect gift. They create simple, nourishing skincare that is perfect for winter with creams and balms that have a smooth, gentle texture and minimal ingredients, which makes them appealing to anyone with sensitive skin or a constant battle with dry air. A small jar is easy to keep on a desk for everyday use and feels like a quiet little luxury during cold months.

Find it here: Coco’s Tallow.

A Classic Candy

Little B Confectionery creates soft, buttery caramels that taste like a homemade treat from a local holiday market. They arrive beautifully packaged and feel warm and welcoming, just like so many Canadian bakeries and small-town sweet shops. A box is easy to share, and the flavor speaks for itself. My Canadian colleague, Christina, gifted me these last Christmas. I can speak from experience that these are delicious!!

Find it here: Little B Confectionary. 

A Well-Sourced Choice

Authentic Indigenous Seafood offers wild salmon products sourced directly from Indigenous fisheries across Canada. Their work supports communities with deep cultural ties to the land and water, and the products themselves reflect that care and history. For colleagues who love cooking or value ethically sourced foods, this gift brings both flavor and meaning. It is a powerful way to highlight a distinctly Canadian story.

Find it here: Authentic Indigenous Seafood. 

A Comforting Cup for Cold Days

Domo Tea blends are made for Canadian winters. Their micro-ground teas dissolve smoothly and create a comforting, rich drink that warms you up after stepping in from the cold. This is a thoughtful choice for colleagues who keep a mug close at hand while working from all over Canada. The flavors feel cozy and familiar, especially during dark winter afternoons.

Find it here: Domo Tea.

A Box That Looks and Tastes Good

Beta5 Chocolates is a Vancouver favorite known for chocolate that looks like art. Their flavors and geometric designs reflect the creativity of Canada’s west coast food scene. Opening a box feels like discovering a little piece of Vancouver, and the chocolates themselves are as delicious as they are striking. If you want a gift with a true Canadian touch of craftsmanship, this is a great pick.

Find it here: Beta5 Chocolates.

Wrapping Up The Season With Gratitude

Choosing a gift for your team does not need to feel complicated. At its core, gifting is simply a way to acknowledge the moments you shared this year and the people who helped you through them. A thoughtful pick can be anything from a small treat to a practical favorite to a shared experience that becomes a story people retell later.

As you think about your list, consider what makes each person light up. Notice how they spend their days and what they reach for when they need a boost. Meaningful gifts are less about cost and more about sincerity. A well–chosen item can say far more than something grand.

Teams remember how it felt to be supported and seen, and that feeling lasts much longer than any holiday season. My hope is that this guide gives you inspiration for the people who make your workdays better.

If you have a go–to gift that always lands well, I would love to hear it. And while you are taking care of everyone else, I hope you give yourself a little room to rest too. The holidays feel sweeter when we slow down enough to enjoy them.

Warm wishes and Happy Holidays from all of us at Briefcase Coach.