Sending a holiday greeting to a client or a boss feels like walking a tightrope. You want to be warm, but not weirdly personal. You want to be professional, but not so stiff that you sound like an automated billing notification from 2004. Most people overthink it. They spend twenty minutes staring at a draft, wondering if "Warmly" is too intimate or if "Best" is too cold. Honestly, the stakes are lower than you think, but the impact of getting it right is huge for your networking game.
So, how do you wish someone a happy holiday professionally without making it awkward? It starts with knowing your audience better than you know your own LinkedIn bio.
The Fine Art of Not Annoying Your Clients
Context is everything. If you’re emailing a long-term partner you’ve grabbed drinks with, you can skip the formalities. If it’s a high-value prospect you’ve only spoken to twice, you need to rein it in. Business etiquette expert Jacqueline Whitmore often notes that the best greetings are those that focus on the relationship rather than the holiday itself. It’s about the "thank you," not just the "Merry Christmas."
Don't just blast a BCC email to 500 people. That is the digital equivalent of those "Current Resident" postcards you throw straight into the recycling bin. It’s lazy. People can smell a template from a mile away. If you’re going to do it, do it with some actual intent.
Instead of a generic "Happy Holidays," try mentioning a specific project you worked on together this year. It shows you were paying attention. It shows they aren't just a line item in your CRM.
Why "Happy Holidays" is Usually the Safer Bet
There’s a lot of noise about being "politically correct," but in a professional setting, it’s really just about being inclusive and smart. Unless you know for a fact that your recipient celebrates Christmas, Hanukkah, or Kwanzaa, sticking to "Happy Holidays" or "Season's Greetings" is just good business. You don't want your well-wishes to land with a thud because you made an assumption about someone's private life.
It's about respect. Basically, you want to acknowledge the festive season without making it a whole thing about religion unless that's the established culture of your workplace or relationship.
Timing is Half the Battle
Most people wait until December 22nd. By then, everyone has checked out. Their "Out of Office" replies are already live, and they are deep into a third glass of eggnog. If you want your message to actually be read, aim for the second week of December.
Or, even better, try the New Year's pivot.
Sending a "Happy New Year" note in early January is a brilliant tactical move. Your email won't get buried under a mountain of shipping notifications and last-minute deadline requests. It stands out. It feels fresh. It also gives you a natural opening to talk about "looking forward to working together in the coming year." It’s proactive.
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The LinkedIn Factor
Should you post a public holiday greeting? Maybe. But a direct message is infinitely more powerful. A public post is "look at me," while a DM is "I'm thinking of you." If you’re wondering how do you wish someone a happy holiday professionally on a platform like LinkedIn, keep it brief. Two sentences max.
"Hi Sarah, it's been great collaborating on the Q3 rollout this year. Wishing you a relaxing holiday break and a fantastic start to 2026!"
Simple. Clean. Professional. No emojis of dancing Santa Clauses required—unless that’s your brand.
Real Examples for Different Scenarios
You can't use the same tone for your CEO as you do for the freelancer who helps you with graphic design. It doesn't work.
For a Client You Value:
"It’s been a pleasure working with your team this year. We truly appreciate your partnership and wish you a restful holiday season." This acknowledges the business value without being overly sappy. It’s a classic for a reason.
For Your Direct Supervisor:
"Thanks for all the support and guidance this year. Hope you have a wonderful break with your family!" It’s personal enough to be human but keeps the hierarchy intact.
For a Remote Colleague:
"Happy Holidays! Hope you get some well-deserved downtime away from the screen. Looking forward to catching up in the New Year." This is great because it acknowledges the "Zoom fatigue" we all feel. It’s relatable.
The "No-Gift" Policy Reality
Sometimes, the best way to wish someone a happy holiday is to respect their company's gift policy. Many corporations—especially in finance, government, or law—have strict rules about what employees can accept. Sending an expensive gift basket can actually create a massive headache for your contact. They might have to report it, return it, or even face disciplinary action.
Check the policy. If you really want to show appreciation, a handwritten card often carries more weight than a $50 box of chocolates that will just get eaten by the night shift anyway. A card sits on a desk. It’s a physical reminder of a positive relationship.
Cultural Nuance and Global Business
If you're working with international partners, do your homework. In some cultures, the Gregorian New Year isn't the big one. Lunar New Year might be more significant. Or perhaps they are in a region where the "holiday season" doesn't align with the Western calendar at all. Sending a Christmas card to a partner in a country that doesn't widely celebrate it can look a bit culturally tone-deaf.
When in doubt, a "Year-End Thank You" is a universally safe and appreciated gesture. It focuses on the calendar year of work, which everyone shares, regardless of their personal beliefs.
Avoiding the "Cringe" Factor
We’ve all seen it. The corporate holiday video where the accounting department does a choreographed dance to Mariah Carey. Please, for the love of all things holy, don't be that person.
Professionalism is about dignity. You can be joyful without being performative. Avoid:
- Overusing exclamation points!!!!
- Using weirdly personal sign-offs like "Love," or "Hugs."
- Sending messages on Christmas Day or New Year's Eve (schedule them for work hours).
- Making jokes about "drinking too much" unless you are very close with the person.
The goal is to reinforce a bridge, not burn it down with a lapse in judgment.
Actionable Steps for Your Holiday Outreach
If you are sitting there with an empty Outlook draft, follow this sequence to get it done effectively.
- Segment your list. Separate your "Inner Circle" (people you talk to daily) from "Peripheral Contacts" (people you want to stay top-of-mind with).
- Choose your medium. Email is standard. LinkedIn is okay for casual professional ties. Handwritten cards are the gold standard for high-value clients.
- Pick a specific "Thank You." Find one thing that person did this year that you appreciated. Write it down.
- Keep it short. No one wants to read a three-paragraph essay about your year.
- Double-check spelling. Nothing kills a professional greeting faster than misspelling "Hanukkah" or, worse, the recipient's name.
- Set a deadline. Get these out by December 15th or wait until January 5th.
The most important thing is sincerity. If you genuinely appreciate someone's work or partnership, let that be the core of the message. Everything else is just wrapping paper.