We’ve all experienced that moment where it suddenly occurs to us, “We should send something…”.  And just like that, another round of last-minute gifts goes out the door with little more than a hope they’ll “land well.”

If you’ve ever wondered whether your gifting efforts are actually working, or if they could be doing more, you’re not alone. In fact:

• 36% of companies say they struggle to find gifts that truly make an impact.

• 31% want their gifts to help them stand out.

• But only 28% have a real strategy behind what they’re sending.

That means the majority of businesses are spending money on gestures they hope are meaningful but aren’t sure.

And that’s where strategy comes in.

The Real Barrier to Effective Gifting

When gifting is treated like a checklist item, it quickly becomes transactional. But impactful gifting, the kind that creates real emotional connection, requires intention. 

At The Expressory, we ask - “What story is this gift telling?”

Without that story, a gift is just stuff. And nobody remembers stuff.

Here’s what we see all the time:

• Gifts that are reactive

• Gifts that are generic

• Gifts that don’t make anyone feel seen or valued

And that’s where most businesses lose the chance to build emotional loyalty and any kind of lasting relationship with the recipient.

Our Definition of a Gift (Hint: It's Not the Item)

At The Expressory we see gifting as any intentional act of giving that shows you care, with no expectation of return.

It’s not about the product. It’s about how you make someone feel.

Why These Matter More Than Items

If the gift is meant to make the recipient feel something, the best approach is to make sure it has some kind of story.  A theme is what gives that story structure. It’s what connects the dots between your intent and the recipient’s experience.

A theme transforms "things" into a thoughtful, relationship-building experience.

And yet, most companies skip this part completely.

Instead of “What’s a good gift we can send to everyone?”, the better question is:

“What message do we want to send to this person?  And what can we send that reflects that message?”

How to Discover a Gift Theme

Before you can uncover a meaningful theme, you have to slow down and really look at who this gift is for and what’s going on in their world.  

This part is where many well-meaning businesses go off track.

Instead of basing a gift on assumptions or generalizations, the foundation of strategic gifting is research. You’re trying to create an experience based on the uniqueness of the recipient. And the only way to do that well is to take the time to understand them.

Step 1: Prioritize the Relationships

Not every connection needs the same investment. Identify the categories of relationships that attention now. This can be clients, strategic partners, or prospects.  

Step 2: Research Your Contacts

Yes, real research.

You want to gather both qualitative and emotional insights. Look into:

• What accomplishments, transitions, or milestones they’ve recently experienced

• What values, causes, or interests they share publicly

• The goals and challenges of their industry or even their company

• Awards

• Conferences or events they participate in

This isn’t about “what’s their favorite snack” (though fun details help!). It’s about building a real picture of who they are and where they are in their journey.

Step 3: Analyze for Themes

Once you’ve done the research on your priority contacts, it’s time to find the patterns.

Look through your notes for recurring values, goals, challenges, or even language. This is where common threads, your themes, start to emerge. These aren’t just surface-level preferences like “likes chocolate.” We’re talking about deeper signals, like:

• A focus on building team culture

• Anxiety around rapid growth

• Passion for legacy-building

• Desire for work-life balance

To make this process easier (and faster), we often recommend using AI to assist in spotting those emotional keywords and repeated concepts across your research notes. You can even ask tools like ChatGPT to identify common pain points or motivators and cite where they came from so you can validate what shows up most.

Once you identify those themes, they become your foundation. They’ll guide what you give and what you say, ensuring each touchpoint resonates with what truly matters to the recipient.

This isn’t just about being personal. It’s about being purposeful. When you take the time to understand what truly matters to someone and build your gifting strategy around that insight, the guesswork disappears. You're no longer hoping a gift will land.  You’re creating a moment that’s guaranteed to resonate. And that’s when gifting becomes a tool for real relationship building and long-term loyalty.

What You Should Be Asking Yourself Now

Now that you’ve seen what’s possible when gifting becomes strategic, here are a few questions to help you reflect on where your approach stands—and where it might need a little more intention:

1. Do I really know what matters to the people I’m sending gifts to?
   If you had to pick a theme for each of your key relationships right now, could you?

2. Am I doing the research or just relying on guesswork?
   Thoughtful gifting starts with knowing, not assuming. Do you have a system to track what you learn about people?

3. Have I prioritized who I’m investing in right now?
   Are you clear on which clients, partners, or prospects need the most engagement and why?

4. Are the gifts we send actually tied to the message we want to send?
   If your gift isn’t aligned with the recipient’s world, it might just be noise.

5. Could our next round of gifting tell a better story?
   Imagine a theme that speaks directly to where someone is in their journey. What would that look like?