How to Give Great Gifts

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Being a good gift-giver is a high-leverage skill. It helps you make a positive impression on your professional contacts, strengthens your existing network, and makes special occasions with friends and family fun. And knowing how to give great gifts carries over from one job or career to the next.

But honestly, I used to hate giving gifts.

I felt like I was awful at it. And that to be good at it, you had to shell out an arm and a leg.

So I defaulted to what I could figure out: thank you cards and gift cards.

(Don’t give people gift cards unless you want to say, “this is a totally obligatory interaction and I couldn’t think of anything better to give you.” Especially Amazon gift cards. That’s essentially just giving the person cash.)

Eventually, I got sick and tired of feeling like I wasn’t good at giving gifts, so I told myself I’d become good at it. Gift-giving is a skill like anything else, so with some study and practice, I should get better, right?

Now I’m happy to say that I am good at gift giving. In fact, I’d say I love the opportunity to give people gifts. It’s not just fun and great at building social capital in business contexts, but it’s also a game.

Aim for making the person think that you know them better than they know themselves.

That’s when you know you’ve successfully given a gift.

Listen, Pay Attention, and Do Your Research

Becoming a great gift giver comes down to becoming a great listener, looking for details, and viewing other people as complex people like yourself.

Most people view gift-giving as this thing you do a few times every year and you just send the person whatever they told you to send them. That’s straightforward, sure. But it doesn’t have the impact and the lasting effect — that feeling of, “oh, you shouldn’t have!” — on the person that great gift-giving does.

That’s because it takes work to listen to people in a way that gives you helpful information about what kinds of gifts you should give them.

It takes work but it isn’t hard.

Listen for Problems

My go-to way of finding out what kind of gift to give somebody is to listen directly to what they say.

No, I don’t mean “ask them what they want and buy it for them.”

I mean, look for what their problems are and ask yourself, “what can I get them that would solve this problem?”

Everybody has issues they want solved and they probably voice these issues to you in passing. Maybe their shoes are leaky, they don’t have enough time to cook, they want to decorate their walls more, or their back has been killing them.

Get them a gift that solves these issues for them. And even better — that they know would solve these issues for them but that they won’t buy for themselves, for some reason.

People intuitively get this when they give gifts around big life events like weddings and baby showers — when they go and buy toys for the nursery or a gift for the newlyweds that they can use together — but it seems to get lost in normal gift giving.

But outside of these events, people ask “what does this person like? What are their tastes?” instead of asking, “what can I get this person that they’ll like but that also helps improve their life right now?”

Example: My Mom’s Birthday

My mom spends a lot of time on her feet at work. She works late doing sales and interior design work. She’s exhausted by the time she gets home. And she always tells us how exhausted she is from work when we talk to her.

She also doesn’t eat as well as she knows she could eat. And she values having her kitchen in pristine, clean shape. A single drop of grease on her range irritates her more than not eating because she’s tired does.

So, you have somebody who wants a convenient, clean way to make meals for herself when she gets home from work.

She needs something like an air fryer.

I could have just gotten her a dinner and some kind of gift men get their mothers for their birthdays (perfume? I don’t know.). Instead, I ordered her an air fryer from Costco (Gourmia 5 Qt Digital Air Fryer, $59.99).

(My mom isn’t the type of person to effusively gush over a gift, so this was a pleasant surprise.)

This gift solved a problem for her that she’d been speaking about. And it also solved a secondary problem (“I don’t know how to use it”) by including an auxiliary gift with the air fryer: a cookbook for air frying foods.

Look for Non-Obvious Quirks

Sometimes it isn’t obvious that the person has a problem you can solve with a gift. Maybe they just have little quirks and tastes that you’d really like to get them a gift related to those quirks.

This works well because these quirks should be non-obvious. They should be personality traits, tastes, and preferences that you could only pick up on if you knew the person pretty well.

(This is also why generic gift cards aren’t a good gift. They say, “I don’t really know anything about you, so here’s money.”)

So pay close attention to tastes and preferences that reveal interesting quirks about people.

Some quick and easy places to look:

  • What do they drink? Do they like a particular kind of coffee? Wine?
  • What do they wear? Do they defer to a specific brand? Or a specific style?
    • (Note: Clothing is hard because sizes are tricky. Take style tastes as an indicator for how you could gift accessories, which are usually easier to size.)
  • What do they read? Do they like a specific genre? Author?
  • Where do they spend their free time? Do they like concerts? Do they like courses? Do they like sports? If so, where and with whom?

I start by asking, “where does this person spend their disposable income?”

And then asking, “what can I get them that speaks to this but that they wouldn’t get themselves?”

Then go after that.

Example: Girlfriend’s Birthday

I really enjoy Ramit Sethi’s content. So does my girlfriend. It’s actually one of the first things we bonded over on our first date.

For her birthday, I wanted to get her something that spoke to non-obvious quirks about her personality but also was something she’d never get herself.

I had the opportunity to sit down with Ramit in NYC to discuss a few items that I wanted his input on. Before the meeting, I picked up a copy of his book, I Will Teach You To Be Rich, and stuck it in my bag. Before digging into the meat of my questions with Ramit, I asked him to sign and personalize it for her birthday.

Not only did this make a great gift, it was also fun for Ramit to sign a copy of his book (most authors actually enjoy doing something like this if you ask them politely and make it easy for them to do).

Do Some Sleuthing

If you can’t find obvious problems or parse out quirks in somebody’s personality, do some research on them and listen closely to what they talk about to better discern their tastes. If you have to give somebody a gift based on tastes alone, don’t make an inference based on something as broad as “oh, she’s a woman, so I am sure they like flowers,” or “oh, he’s a guy, so I am sure he likes sports.”

Sleuthing can be as detailed as looking up people’s addresses on Google Maps and looking at their neighborhood, researching their blog or personal website, or finding any media they created or are featured in.

Or it can be as simple as paying attention to what they say in conversation or post on social media.

Example: Thanking My Literary Agent

My literary agent went above and beyond in helping me land a book deal. She pushed me to put together a great proposal and landed me phone calls with several top-tier publishers in less than two weeks. And she got me a deal that was beyond my expectations from a publisher I wanted to work with.

And she had mentioned in passing during a call that she liked wine. And she was familiar with Gary Vaynerchuk and his rise to prominence.

So I got her a subscription to the Gary Vee Wine Club (Gary Vee Wine Club from Wine Library, $55/month) as a token of my appreciation.

(I forgot to send a note saying it was from me…hence the second line.)

Ask Other People Who Know Them Better

Sometimes you just can’t figure out what to get somebody. In that case, defer to somebody who knows them better.

A simple email or text message like this works:

Hey [First Name],

I’m looking at getting [giftee’s name] something for [reason]. But I’m not sure what to get them.

Do they like [option A][option B], or [option C]? If not, do you know what they would like?


[Your name]

Throwing out a few ideas as options makes this email or text easier to reply to. If you tell people, “what do they like?” you may not get a response because that’s so open-ended.

Example: Thanking a Local Finance Executive

A local finance executive here in Pittsburgh recently gave me half an hour of his time to discuss fundraising. He has experience both in private equity and venture capital, so I wanted to get his perspective on how to raise money locally. He’s a Very Busy Person, and I was honestly a little surprised he agreed to meet with me relatively quickly.

He’s also the colleague of a good friend of mine. I had no idea what to get him as a thank-you for his time, so I asked my friend.

“He likes wine. Red. There’s a merlot he likes that I got a few months ago.”

So I bought that and had it sent to him. He was taken aback (but not so much that it was weird – the bottle was only $30) and appreciative.

Some Rules About Giving Gifts

There are good ways and bad ways to give gifts. Try to avoid some common mistakes (including mistakes that I, myself, have made).

When to Give Gifts

You shouldn’t always give people gifts. You can go too far in sending somebody a book, a bottle of wine, or some kind of toy. You can appear transactional.

And the number 1 rule of building a world-class network is don’t be transactional.

Gift giving has a sort of implied reciprocity that, if there isn’t some kind of reciprocity already set up, can make the relationship awkward. In other words, you don’t want to make that person think they owe you something when they previously didn’t.

This is why a lot of professionals won’t accept gifts (Sol’s policy here is a good example). It’s not that they don’t want to take your nice offer of a bottle of wine or a book, but that they don’t want to get into the awkward power dynamics games that can come with that.

So, as a good rule of thumb, it’s acceptable to give gifts to these people:

  • Close friends
  • Family
  • Professionals who have gone above and beyond in your expectations of them
    • Example: I have an accountant who recently took up a tax issue for me and resolved it quickly, even though she could have told me no or could have charged me an exorbitant rate. She went above and beyond. I wanted to thank her so I sent her a bottle of wine.
    • Example: When I build business partnerships with companies who go out on a limb to work with me, I send them a gift as a thank you around Christmas time. They like it and it makes a good impression.

If you have to ask, “would this be weird or creepy?” the answer is probably yes. Just defer to a thank-you card in that case.

Proportionality of the Gift

An important thing to keep in mind is proportionality.

Don’t buy somebody a car for meeting with you.

Don’t gives somebody a gift card for helping you get your dream job.

If somebody does something massively helpful for you and exceeds your expectations, get them a gift that just slightly exceeds their own expectations. Be proportional about your gift-giving. Some of the best gifts don’t cost a lot to get but communicate great care and research when putting them together. Those are harder to be disproportionate about than just shelling out money.

Don’t Give Gifts that are Burdens

Any gift you give should bring more utility to the person you’re giving it to than it takes away.

Some gifts require maintenance. Nice shoes are an example of this. While a nice pair of shoes can be a great gift for somebody who likes shoes, make sure that whatever it costs to maintain them (i.e., get them shined, conditioned, reheeled if old) is a relatively small cost to the person to whom you’re giving them.

Memberships and trips are also costly. While plane tickets to Florida may not cost a lot if properly purchased, putting somebody in a position where they feel obligated to shell out money for a hotel room is uncomfortable and can backfire.

Remember to Include Notes

I’ve made the mistake before of sending somebody a gift only to later learn I never put any indicator on it that it was from me.

If you can’t send a note with the gift, send along a thank-you card indicating that you also sent them the gift.

Send Thank-You Cards

If you can’t think of a gift or a gift would be out of place, just write a handwritten thank-you card. People appreciate handwritten cards if sent and conveyed sincerely.

(This is the one area I need to get better at myself – but every time I have taken the time to send a card, people appreciated it.)

Learning how to send gifts well can set you apart from your peers and make a positive impact in the minds of your friends, family, and acquaintances. Plus, it’s fun. Take the time to learn how to do it.

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