THE $8,000 HOLIDAY GIFTING MISTAKE

A couple of weeks ago, a new client came to me with a very familiar problem.

Last year they spent $8,000 on holiday gifts.

200 gifts. Nice stuff. Good packaging. Logo front and center.

And what did they get?

12 thank-you emails (that’s about 6%).
Zero meetings. No. momentum.

The issue wasn’t the budget. It was the plan. There wasn’t one.

Here’s the truth: price ≠ thoughtful.
And putting your logo on something doesn’t automatically make it useful.

Where it went sideways

They did what most businesses do every December:

1. Everyone got the same gift. VIP clients, warm leads, “met once at an event three years ago”… all treated like they had the same value.

2. They sent it when everyone else did. Mid-December. Their gift landed with 47 others and blended into Gift Mountain 2024.

3. No follow-up baked in. They shipped and hoped. Then January rolled around and they were back to cold outreach. The gift didn’t create a conversation because they didn’t tell it to.

So we reworked it.

What we’re doing this year instead:

1. Segment ruthlessly

Not everyone gets the same thing.

• Top 20 clients: premium, useful, keeper-level. Desk worthy. Long-term visibility. (I’ve got a product that’s still being seen after 29 years—see the link below.)

• Active clients: still good, still on-brand, solves something for them. Shows you see them—without blowing the budget.

• Warm prospects: thoughtful, daily-use. You want to stay present.

The point: match the gift to the relationship, not to what you think “holiday gifting” is supposed to look like.

2. Send before the December avalanche

Ship in late November or very early December.

That way your gift shows up when people are planning, not drowning. Fewer boxes = more attention. You stand out because you arrived early, not because you spent more.

3. Make the gift do the talking

The gift isn’t the outcome. The conversation is.

Include a short personal note and a reason to follow up—so when January hits, you’re circling back to something warm, not another “just checking in” email.

And don't be surprised when you receive a thank-you first. (Because that's what happens when you choose the right gifts for your clients.)

The real point.

Holiday gifting isn’t about doing it because "we do it every year." It’s about staying top-of-mind when Q1 decisions get made.

The gift opens the door.
Your follow-up walks through it.

So ask yourself:

“Is this gift starting a conversation—or ending one?”

What to do now

Before you order anything:

• List your top 20.

• List your active/recurring clients.

• List the warm prospects you want to keep close.

• Pick a ship date before the chaos.

• Write the follow-up you’ll send after it lands.

Next week I’ll dig into how to choose gifts people actually want to keep (and not toss in the break room).

—Barbara

I’m Barbara Hobart. Since 1994, I’ve helped everyone from E! Entertainment Television to Fortune 500s to growing businesses turn branded merch into a strategy that gets remembered—not landfill with a logo.

P.S. Want to see what long-term ROI looks like in real life? I just dropped a YouTube video about a T-shirt I created for E! Entertainment's True Hollywood Story that people are still wearing 29 years later. Watch it here.