The art industry, like any other, is built on relationships, and one of the relationships at its very foundation is the one between artist and gallery—boiled down to the simplest terms, between the person who makes the work and the person who sells it.

As they hammer out the terms of the relationship, it’s crucial that artists ask the right questions, from how the dealer understands the artist’s work to the nuts and bolts. The two parties are often friends, but in the end, this is a negotiation between two businesses, and in business, no one likes surprises. Artnet News surveyed a number of artists who show with galleries small and large about the kinds of questions artists should ask a prospective dealer (including the kinds of questions they wish they themselves had asked). So that they could be frank, all spoke off the record. 

First of all, they stressed that artists must do plenty of research. To protect themselves, they should get in touch with the gallery’s artists, as well as those who have left the stable, to find out whether it’s a supportive environment and, crucially, whether artists get paid promptly for the sale of works consigned to the gallery. “It’s surprising how many galleries fail that test,” said an artist in their 50s who shows at one of the world’s largest galleries. (One New York artist who has shown throughout the U.S. and has had bad experiences suggests that artists could be as cheeky as to ask a New York dealer if they have read the state’s consignment laws, which dictate that dealers maintain a separate bank account for the artist’s share of the proceeds.)

“Talk to other artists and see if they’re happy,” said the 50-something artist, “with the caveat that a lot of artists are terminally unhappy narcissists.” Artists should keep in mind that just as they’re asking around, the dealer is doing the same, warns one artist who is also a gallery co-owner.

It might seem as though dealers have all the power; regarding questions to ask before a show, one artist joked that the typical attitude is, “If they’re going to give you a show, there are no questions.” But several artists described these negotiations as an opportunity for artists to advocate for themselves.

“Communication is key,” says the artist/dealer. “You want to not be afraid to discuss nitty-gritty stuff like what the split is, how often work will be shown, and what representation entails.” Both sides should be able to take their time, they add; negotiations shouldn’t take place under pressure. 

“You should think about it as getting married,” the artist in their 50s said. “It’s very difficult to get divorced and very not fun to leave a gallery.” 

Here are eight questions artists may want to ask:

1. Who are you, anyway? 

If they haven’t already, this can be a time for artists to get to know the dealer, one artist points out, by asking questions like, “What dealers do you admire? How did you get into this line of work?” After all, they point out, it’s a largely unregulated field, where anyone can call themselves a dealer. Even though artists wouldn’t say it, they should be thinking, Why should I trust you?

2. What do you see in my work? 

It’s essential that an artist find a gallery that provides the right context for them. So the artist might ask the dealer what they see in their work and why they are interested in it. 

“I’m most comfortable in situations where it’s clear that the person who shows my work has a deep and profound appreciation for it,” says an artist in their 40s who has had solo shows at galleries throughout the U.S.

3. Who pays for what? 

“It’s very important to ask about the breakdown of the financials,” says an artist in their 50s who is represented by galleries worldwide. Who will pay to photograph, ship, insure, and (if necessary) store the work?

“We’ve had artists lay out terms and ask astute questions,” says the artist/dealer. “For example: What happens with work that doesn’t sell? Who pays to ship it back? Who pays to store it? If the work in a first show doesn’t sell, will there be a second?”

Many artists’ work involves considerable up-front production costs, and artists will need to know the gallery can foot the bill for fabrication, in part or in full, and what the terms for reimbursement are. An artist in their 40s who has had solo gallery and institutional shows internationally said that they left a gallery partly because the dealer wasn’t willing to pony up for production. 

4. Where will the work end up? Where shouldn’t it end up?

Since dealers will take some of the sale proceeds (typically about half), they have to offer access to collectors who will be committed to supporting the artist. An artist in their 40s who sells work to their lively Instagram following said that artists should ask, “‘Am I expected to bring a set of buyers, or will you be able to sell my work to your existing clientele?’ You have to know they are bringing something to the table. Ideally you want them to say, ‘This is where I can see your career going.’” This artist also stressed that the gallery should bring access to journalists and curators. 

Conversely, the artist may want collectors to be vetted for certain red flags. They may not want the work to go to collectors who have made their money from arms dealing, or who own companies that are harmful to the environment. Especially in the wake of the Israel-Hamas conflict that has sharply divided the art world, artists may wish not to sell to institutions that are funded by the Israeli government.

5. What do you expect in terms of sales?

If the principal thing the gallery does is sell the artwork, the artist shouldn’t be shy about prices and revenues. What does the dealer plan to charge for the work? Some are bold enough, says one artist, to ask how much work the dealer thinks they can sell in a year. 

6. Who will be my main contact at the gallery?

Young artists showing with emerging galleries may be able to count on access to the principals, but those who show at larger galleries will likely be in close contact with one of the gallery’s directors (who, as Artnet’s Annie Armstrong recently reported, can be crucial to a gallery’s success). It’s important to know how much autonomy the director has and what the artist’s relationship with that person will be like, says an individual who shows with a mega-gallery.

7. What’s the five-year plan?

Just as the classic job interviewer asks where the applicant sees herself in five years, the artist will want to know the dealer’s ambitions, not only for the artist but also for themselves. Does the gallery plan to, say, expand to Seoul in the next five years? If the owner is advanced in age, will the gallery be winding down operations soon, or is there a succession plan? 

8. Can I have that in writing?

The art world is, to a large extent, a handshake industry. “I’ve heard of these mythical contracts,” said the artist who shows with a mega gallery, “but I’ve never seen one.” But some indicate that this may be changing. “Despite all the feelings that this is such a huge opportunity and you don’t want to fuck it up, you should protect yourself a bit,” says one artist. 

This is one place where artists can try to avoid the fundamental problem many were so quick to cite, about not getting paid promptly. The artist with the lively Instagram following, for example, pointed out that some artists request an agreement whereby, when sales occur, the proceeds go to an intermediary who splits the money between the dealer’s account and an account dedicated to the artist’s share of the proceeds. 

That said, added the artist, “Some things are going to go to shit.”