The calendar may say mid-November, but guess what? There’s still time to make a big impact with your holiday appreciation. Even if it means not a December holiday.

In fact, showing gratitude only takes a little intentionality and a few meaningful touches. It’s never too late to make someone feel seen.

Whether you’re behind on your usual outreach or just now thinking, “Should we send something this year?” you’re in the right place. Because even with a short timeline, you can still create gestures that deepen loyalty, spark conversations and stand out in the sea of generic holiday noise.

Let’s walk through how to pull off a thoughtful, low-stress holiday appreciation plan that feels as good to give as it does to receive.

First, Take a Breath

Here’s the truth most “holiday strategy” blogs won’t say: appreciation doesn’t expire on December 25th.

In fact, January is one of the most overlooked and perfect moments to show gratitude. Why? Because your gesture won’t be lost in a sea of branded swag and sugar cookies. It’ll stand out when it arrives with intention and calm after the holiday frenzy.

Whether you send something tomorrow or three weeks from now, it’s the meaning that matters most. What we’re saying is – You have options when it comes to holiday marketing strategies for business​.

Your 4-Step Holiday Appreciation Triage Plan

If you’ve got limited time, budget or brain space (or all three!), here’s a simplified plan to make it happen without losing your mind:

Step 1: Prioritize Who Matters Most

Start small. You don’t need a 300-person mailing list. Focus on the relationships that matter most right now:

• Your top-tier clients – That could be 10

• Any loyal referral partners

• Strategic collaborators or vendors

• Key employees or team leads

• Any prospects you’ve been courting

Don’t overthink this step. And don’t complicate it by bringing in budget constraints right now. Just make the list, and you can create tiers as you go.

Step 2: Choose a Thoughtful Gesture or Holiday Appreciation Gift (That You Can Actually Deliver)

Skip the overdone food baskets and mass emails. Instead, focus on small gestures with meaning. Some fast-turnaround options:

• A gift card paired with a heartfelt message specific to something in the recipient’s world.

• A handwritten card with genuine messages of gratitude or acknowledgement. Meaningful words go a long way in a relationship. Think of how you could celebrate the person.

• A charitable donation made in their name, tied to a shared value.

• A locally-sourced item that shares a little something about you or your team to make the recipient feel part of your community.

Keep it simple. The magic is in the message, not the price tag.

Step 3: Don’t Obsess Over Timing

If you can’t make it by Christmas, no problem! You’re officially ahead of the New Year’s curve. Stress removed.

Frame your gesture or holiday appreciation gift around themes like:

• “Thank you for sharing this year with us. <insert an observation about what they’re working toward.>”

• “We’re so grateful to have worked with you in 2025. <insert acknowledgement of some type of shared experience together – Remind them of something good.>”

• “Here’s to starting 2026 with appreciation and intention. <insert a nod to the goals for 2026 and how you believe in them.>”

No matter when your touchpoint gets in the mail, the words you choose will create an emotional impact that is lasting for that relationship.

Step 4: Follow Up with Connection, Not Just Delivery

The appreciation touchpoint shouldn’t be the end of the interaction. You want this to be the start of additional conversation when possible. You should always have a plan for the next outreach.

One way to do this is to close your message with some type of question or prompt. Examples include:

If the gift was a book: “Be sure to let me know what you thought about chapter 6.”

If it was a gift card: “Let me know how the family enjoyed, xyz.”

If it was a journal: “You’ll have to share some of the goals you decided on in your journaling efforts this month.”

Closing prompts encourage additional follow-up. Even if you don’t include one, be prepared to engage if the recipient should reach out with a thank you. Think about something you can ask in return when they do call or email. Consider asking what type of exciting activities they took part in over the holiday months. This gets them thinking about positive things and elicits positive reactions in the brain.

Finally, don’t be discouraged if you don’t hear anything in return. Just be prepared for your next outreach. After your gift or message arrives, look for an opportunity to send your next message or make a call about 4-7 weeks later. Have a reason to be helpful. Keep the conversation going.

Gratitude is great, but relationship-building is the real ROI.

A Note on Personalization

Even in a rush, personalization matters. Studies show that segmented email campaigns can generate 760% more revenue than non-segmented ones.

Even though that’s an email stat, it still illustrates something we know to be true in gifting, as well.
When a gesture feels like it’s just for the recipient, it has more impact.

So even if you’re sending the same gift to 10 people, tailor the note or message for each recipient. Mention a project you worked on. Reference a moment you appreciated. Show them they’re not just another name on your list.

Still Stuck? Here’s a Simple Formula:

If your brain is spinning, here’s a formula you can use for any last-minute appreciation note:

“We’ve been reflecting on what made this year meaningful, and your relationship was at the top of our list. Thank you for [specific detail]. We’re grateful to know you, and we’re excited to see where 2026 takes us together.”

Keep it short, specific and heartfelt.

Reflect and Rebuild: 5 Questions to Ask Yourself

1. Am I focused on impact over volume?

   Would 10 deeply personal gestures go further than 100 generic ones?

2. What do I want the recipient to feel when they receive this?

   Joy? Validation? Encouragement? Let that shape the gift.

3. Is there still time to make this meaningful without rushing it?

   Can I shift my mindset from “late” to “early New Year”?

4. What details or moments from this year can I reference to make it personal?

   A great project, a shared laugh, a milestone. Even small things matter.

5. What would I want to receive right now?

   Would it make me feel seen, appreciated and excited for what’s next?

At The Expressory, we believe that any moment of appreciation is an opportunity to deepen the relationship.

If your holiday planning slipped through the cracks, take this as your chance to build something even better. This could be a gesture that feels intentional, even if it wasn’t mapped out in July.

And if you’d like help making that happen?
That’s exactly what we do. Get started by joining our next Q&A session
Or schedule a one-on-one. Let’s make sure your appreciation doesn’t just get delivered, it gets remembered.

Frequently Asked Questions on Holiday Appreciation Gifts

How can I make my holiday appreciation gifts more personal?

The key is showing your recipients that you know them. Think about their interests, your past interactions or what they’ve enjoyed in previous years. Personal touches, like a handwritten note, custom packaging or a small item that reflects their personality, can make even a modest gift feel meaningful.

Do I need to send the same holiday gift to every client or employee?

Not at all. While it’s easier to order in bulk, mixing it up based on your relationship or their role can make a bigger impact. A thoughtful variation (like different gift tiers or personalized touches) shows that you’ve really considered each person, rather than just checking a box.

What’s the difference between holiday appreciation gifts and regular promotional gifts?

Promotional gifts are about brand visibility. Things like pens, mugs or other swag that keep your name in front of people. Holiday appreciation gifts are about gratitude and connection. They’re meant to say, “We value you,” and should feel personal, thoughtful and memorable, rather than purely functional or self-promoting.

How can small businesses manage holiday gifting on a budget?

It’s really all about planning and creativity. Set a clear budget per recipient, prioritize your top clients or employees, and look for gifts that feel personal without being expensive. Even a well-chosen, thoughtful gesture can have a big impact without breaking the bank.