Authenticity, rapport, and attention to detail: the best gifts don't fit in a box.
February 19, 2026
By Rachel Smith
Originally published December 2020. Updated February 2026.
A gifting guide? In February?? The kind of gifting we’re talking about has nothing to do with holidays, birthdays, or any other traditional gift-giving period. We’re talking about gifting prospects, current clients, and past customers as part of your regular sales strategy. Wisely-chosen personal and professional gifts will make you stand out in the increasingly automated world of sales.
Strategic gifting in sales can give you an edge. Even if it doesn’t end in a closed deal, you’re still better off for it. The act of giving a gift triggers the mesolimbic reward system in our brain. It makes us feel good. Why are we hard-wired to like presents? Possibly because gifts have long been important in human societies, as they serve an integration function. They help to build and cement relationships.
Humans have been gift-giving since the beginning of, well, humans. Cavemen gave each other gifts. Granted, they were rocks and animal teeth, but gift-giving is deeply ingrained in our evolutionary history. Even though we love to scroll endlessly on our phones, on the inside, we are still very much cavemen. Gifts make us feel special and strengthen the bonds between us. It might be a low-tech strategy, but it’s still highly effective.
Salespeople are often fighting against the stereotype of the disreputable used-car salesman who is willing to do and say anything to get you to buy. It is (as most stereotypes are) unfair, especially since most sales professionals have chosen their profession because they like to spend time with and genuinely help others.
Part of showing your authentic self, building rapport, and connecting with others (and destroying the negative stereotype) is showing that you’re listening to what your clients and prospects have to say. Gifting is a great way to show you’ve been paying attention. Did a prospect mention their favorite sports team? Is their dog interrupting a Zoom meeting? Details like these are opportunities for you to follow up in a more personal way. Share a news article about their team or send their dog a new toy. That is gifting.
I’m not saying your client wouldn’t enjoy tickets to an upcoming game (and if you can swing that, go for it), but gifting doesn’t have to be a grand gesture. It can be anything, whether digital or physical, that you send their way that’s personalized to them and provides value. If it highlights a connection between the two of you, even better.
Example: A note with a bag of pet treats.
“I noticed your adorable puppy on the call. Mine also always tries to climb in my lap during meetings. These chew treats are the only thing that keeps my dog’s interest, and they last for hours! They have been a lifesaver!”
You spent a few dollars on dog treats. Your prospect is happily surprised, feels a connection to you as a pet owner, and will think about you every time he gives his dog one of those treats.
There are some organizations, for example, state and local governments, that do not allow their employees to accept gifts. It’s important to be cognizant of this, as it can present an awkward situation. Nobody likes to reject someone’s present. Even if your prospect can’t accept physical gifts, that doesn’t mean you can’t send them an article that would interest them, write them a note, or let them know a store near you is closing, and all of their Nationals gear is 75 percent off.
The fact that we’re all working from home can also make gifting a bit more challenging. What would have once been sent to their office now has nowhere to go as it would be creepy to send something to their home address (more on creepy later). What often works in this situation is a link and a gift card. Maybe you can’t send the special dog treats, but you can provide a link and send an Amazon or PetSmart gift card via email.
Can gifts be physical, pricey items that get sent to prospects and clients? Yes. Can you use B2B gifting platforms like Reachdesk or Sendoso to manage your gifting strategy? Of course. Do you need to do that? We say no.
We define a gift as something of value to the recipient, but that doesn’t have to be monetary value. Some of our favorite items to gift are relevant articles. When you come across content related to something your prospect has talked about—a problem they have, their company, their competitors, or industry-specific news—send it along to let them know that (a) you’ve been listening, and (b) they are top of mind. Include it in an email that references why you thought it would be relevant. Point out anything you think will be of particular interest within the article. Finally, ask them to share their thoughts. Monetarily, this costs nothing, but the value it provides to them could still be high, and the message it sends is what’s key.
What are other no-cost gifts your prospects might appreciate?
“Gift” can mean a gift in the traditional sense, but it definitely doesn’t have to.
At Maestro, we like to say that sales is like physics—a deal in motion stays in motion. If a deal is slowing down, it’s a great time to gift. An average salesperson might email and let their prospect know that they’re just following up on a previous message or call, but a savvy sales professional would send along a helpful article about something discussed at the last meeting, or a heartfelt note congratulating the prospect on some exciting company news. You’re much more likely to get a response to an article or a note than to a generic follow-up, and this gets your deal moving again.
There really isn’t a wrong time to gift. In terms of what to gift, it will depend on the person and the circumstances, but keep two things in mind. First, it needs to be personal. Don’t, for example, send a Starbucks gift card to all of your prospects. Some of them don’t drink coffee. In order to build on your relationship, the gift needs to be thoughtful.
The situation we find ourselves in is ironic. We know that everyone likes personalization, so we have implemented new technologies to make personalization faster and easier. You likely have a tool that can track which emails have been opened and send another accordingly. We have essentially depersonalized personalization. The good news for you in this situation is that something as simple as a handwritten note or a thoughtfully-selected article can make you stand out from the crowd.
The second thing to keep in mind is not to be creepy. If you see on LinkedIn that someone is a Duke alum, it would be completely appropriate to send them an article about this year’s basketball team with a note that says, “I thought you would enjoy this since it projects your Blue Devils will do well this season.”
It would be inappropriate to dig around on their Facebook page for more personal information. Maybe you figured out that they have two children and, by reading through comments, know their names and think, “personalized Duke hats for these kids seems like a great idea.” DON’T DO IT. You’ve crossed the line into Creepytown. It will definitely make you stand out from the crowd, but not in a good way. Show that you’re listening to them, not that you’re watching them, Big-Brother style.
Gifting is an effective strategy because it shows prospects that you’re paying attention and that you care. Nobody wants to feel like just another sale. That stereotypical used-car salesman doesn’t remember where someone went to school, that this person’s son plays lacrosse, or that somebody’s rescue dog goes nuts for squeaky toys. But you do, because you are a sales professional. You care, which is why you’re doing this job in the first place.
If you’re interested in learning more ways to keep your deal in motion, reach out at mastery@maestrogroup.co.
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