Mine was "who handles the insurance while the work is on the wall?" Nobody mentions it, nobody puts it on paper, and when my first show got damaged in the install before it even opened, suddenly it was my problem. Live and learn.
What's the one question you wish you'd asked before you signed with a gallery? The one that would've saved you a headache or a loss if you'd known to ask it.
Insurance, yeah. That's a good one and a hard one to recover from.
Mine was about the paperwork for the work itself, the condition report. I had a show where the gallery's install team handled everything, and when I came to collect at the end, two pieces had water damage nobody could explain. No condition report taken at the start, no record of who saw what when, so it was just my word against the air. I signed the contract and walked out with absolutely nothing.
Now I photograph every piece at the door, in front of a staff member, dated. Felt like a paranoid move at first. It's not. It's just prudence wearing a friendly face.
The sad thing is the questions we're all wishing we'd asked are the ones that make you look difficult. But the gallery isn't going to volunteer them, so somebody has to look difficult. Cheaper than learning the way we did. 🙂
The condition report, yes. That's the one that actually haunts people because it's not dramatic, it's a boring piece of paper, so nobody thinks it matters until it's the only thing standing between you and a payout. And then it's everything.
I like the photograph-at-the-door habit. Paranoid until the first time it isn't. The dated part is the key, too, nobody can argue with a file date and a staff member in frame. I started doing a low-res video walk-around instead, same idea, less staging. Just a slow pan, the piece in the light, the room behind it. Two minutes, done.
The humiliating part is that galleries nod along like it's completely reasonable when you do it. Which tells you everything about how many artists got burned the exact same way before you. Nobody's surprised anymore.
Insurance is a good one, and the damage in install before opening is a particular kind of pain because it was never even in the show properly. I've had that happen with a piece that took a forklift hit in the loading bay. Nobody's fault, everybody's problem.
Mine would be: what happens to the work when the show ends and you decide you don't want it back on your wall. Not the sale, not the hanging, but the un-hanging. I had a piece in crates sit in a gallery's storage for two years once because they were "going to find the right moment for a second showing." Found the moment. Eventually. Storage fees were mine.
People fixate on the exciting part of the contract, the percentages and the dates. The boring sentences are where they get you.
The storage question is a good one, and I suspect more common than anyone admits. I was taught early on to put a return of work clause in writing before anything else, and it's saved me more than once. The polite fiction that a gallery is "finding the right moment" tends to stretch precisely as long as you let it.
My own would be about condition reporting, actually. I had a gallery that photographed the work on arrival but never looked at it again until the show came down, and by then the frame had a water stain from a leak in the ceiling I had no proof they were responsible for. Nobody photographs the work on the way out. I always do my own documentation now, before and after, and I date it.
It feels like a small administrative thing until it's the only thing standing between you and eating a loss you didn't cause.
The condition report is the one nobody thinks of as drama until it's the only thing between you and eating the cost. You're right that it's boring, which is exactly why it works. I've started doing my own on arrival now, with photographs, date-stamped, and I email it to the gallery the same day. It's petty and it's tedious and I've never once needed it for anything good. But the one time I do, I'll be glad.
A leak in the ceiling though. That's a special kind of insult. Not even someone doing something stupid, just a building deciding to be a building.
The forklift in the loading bay, that's a whole other level of absurd. At least my damage happened in the gallery itself, in a room full of people who were supposed to be careful. A forklift means the painting was barely on the premises before the universe decided.
And your question about the un-hanging, that's the one nobody asks because you're so relieved to have the show at all that you can't imagine wanting the work back. Two years in crates, that's brutal. I think we all learn that galleries are great at the front end and vague on the back end. The storage clause is the boring piece of the contract that actually matters. I'd rather read fifty pages of storage terms than be charming at one more opening.