The best business-related gift I ever received was the most surprising gift I ever received. An associate called ahead to a nice restaurant he knew I'd be eating at with friends and told the maitre d' he wanted to buy us a round--anything we wanted--at the end of the night. When the waiter informed us, we asked him to order for us; he brought us three very interesting scotches. No drink has ever tasted better.

That gift defined the evening--it made it memorable. It was a kind gift. And it was a risky gift, considering he left the ordering to us. But most important, it was a selfless, thoughtful and surprising gift. Which is what every gift should be. If it's not all three of those things, it's not necessarily a bad gift, but it's lacking. And if you're going to go to all this trouble, why should it be lacking?

First, What Is It That You're Up To?
Before you look for a gift for someone, it helps to ask yourself why you are getting this person a gift. Is it to reward good behavior? Is it to elicit future behavior? Is the gift-giving really just an act of bribery? Is it an attempt to secure goodwill that you might not otherwise receive?

Or a job? Or funding? Or some sort of favor? Or the promise to not file charges? The question is: Is your gift ulterior--consciously ulterior--in some way?

If the answer to any of these questions is yes, it's not necessarily a problem. (Business demands that we test the limits of our moral codes from time to time.) But the point that needs to be made is: That's not a true gift, but something else entirely. It's bribery, or metaphorical back-scratching. And you might as well just go with expensive if you're back-scratching, because the gift has already been corrupted.

What this is going to be about is: gifts. True gifts. The kind that are selfless, thoughtful, modest and surprising. And not necessarily expensive. (Which is nice.)

But What to Give? And Why? And When?
There are times, of course, when a professional success--a round of funding, an anniversary, a promotion, a first-place finish in the human-knot competition at the team-building retreat--demands a gift. What has much more impact, however, is the gift that doesn't celebrate an occasion but celebrates a relationship, the gift that's not tied to an event and instead is tied to who the person is and what they mean to you.

That makes the when easy. Because the answer is: whenever. To determine the what, it's important to get your heart in the right place. And the right place is the recipient. This means actually thinking about what the person might appreciate, rather than reflexively buying a bottle of champagne.

"The single most important thing is to demonstrate you're thinking about them in the choice of what you give," says John Poisson, CEO of Wantful, a San Francisco- and New York-based gift-giving service. "It demonstrates that you're mindful of the relationship, of a thing they've done or the relationship you have as colleagues or as a supplier or as a partner."

The gift should seem exclusive. It needs to be something that seems right for the person you're giving it to and maybe not so right for someone else.

So instead of giving tickets or a bottle of wine or a business-card holder, what you want to do is upgrade. And the way to upgrade is to make the usual unusual. So: tickets to a play you think they'd enjoy because it's set in their hometown; or wine they'd enjoy because the winery is located near a place where they like to vacation; or a set of stationery with their name on it.

Or think back to a conversation. What did they say that you can use as inspiration? Did they say they like Ireland? A bottle of Bushmills. Did they say they have a country house? Bluetooth speakers for the deck. Did they say they like San Francisco? An antique print of the Golden Gate.

But what if you know very little? Easy: You monogram something. The only thing you need to know is a name. A monogrammed object feeds the ego. It suggests that not only is the recipient worthy of owning an object, but that the object is made more valuable by its association with the recipient. You could have a tumbler monogrammed. Or a tote bag, money clip, beach towel, luggage tag, business-card holder, sheath for some sort of sword, the sword, too, a small automobile. Or, uh, stationery.

A Word About Gift Cards
No.

A Few More Words About Gift Cards
"I don't think gift cards make for very nice gifts in any context. I think they're a cop-out," Poisson says. "I think everything about the gift-card experience is the opposite of being thoughtful. I have to articulate to you what I spent, and at the end of the day you have to go pick something out. That's a hassle for everyone."

Gift cards represent a lack of effort. Which is a problem, because a gift shouldn't be merely a nice thing to get, it should be an emblem of consideration, of you sitting and thinking about someone for a few minutes. It's an emblem of time, too--of the length of your relationship and of how long it took to acquire a gift that symbolizes that relationship.

The main principle is: The gift is the giving. Which means it doesn't matter much what you give. It doesn't matter much if the recipient likes the gift or even keeps it. What happens to the gift after you give it is irrelevant. You don't need to find the "perfect gift." Because long after the gift is discarded, another gift will take its place: the memory of you giving it.

 

Key Technical Matters
Characteristics of a great business gift,
in descending order:
Thoughtful
Difficult to acquire
Expensive
Extremely large

Connotations of a great business gift,
in descending order:
Thank you.
It's great being your partner.
Please.
I'm begging you here.
I spent hours whittling your likeness into a piece of oak.

No gift cards.

No coupons for "free hugs to be redeemed at any time."

Anything with your company's logo on it is not a gift.

A promotional watch is not a gift.

A promotional shirt is not a gift.

A promotional pen is not a gift.

A promotional stress-relief toy is absolutely not a gift.

It is also not an effective weapon against stress.

At the end of the day, an employee really wants only one kind of gift: a day off.

Investors want only one kind of gift, too: a return.

And maybe an interesting bottle of whiskey.

And, oh, what the hell, maybe a couple of those shirts for the kids.

But mostly a return.

 

The Ascending Hierarchy of Popular Business Gifts

Gravity penKE: Kept, Enjoyed
D: Discarded
PRG: Possible Re-Gift
PRGINFM: Possible Re-Gift If Not For Monogram
 
Gravity pen just like they use in space!: D
A small plant (cactus): D
A small plant (non-cactus): KE
Golf-theme desk set: PRG
Golf-theme desk set (monogrammed): PRGINFM, so D
Car: PRG for tax purposes
Tickets (excellent seats): KE
Tickets (mediocre seats): PRG unless you can't unload them, in which case KE, possibly D
Expensive bottle of something: Immediate KE
Framed photo of an antique print related to the recipient's hobby: KE