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06 · Learning & Knowledge-Based

Questions to Ask Your Favorite Artist

Questions for the moment you actually get to talk to someone whose work you love, at a signing table, an artist talk, a studio visit or a rare interview. Written to get past the answers they have given a hundred times, and to be short enough to ask in a line that is still moving.

20 questions · each with a note on why · conversation guide

The questions

Open any question for the note

  1. What are you working on right now?

    Why ask it

    A gentle opener that also tells you where they are in a cycle. Someone deep in a new piece answers with texture and detail; someone at the end of a promotional run answers in press-release sentences, which is your signal to ask something they have not been briefed on.

  2. Which of your own pieces do you still like?

    Why ask it

    Note the word still. Artists are usually tired of the popular work and quietly loyal to something that did not land, and naming it is an invitation to talk about the version of themselves that made it.

  3. What were you making right before the work most people know you for?

    Why ask it

    The years just before recognition are the least documented and the most interesting. This is where you hear about the failed project, the abandoned medium, or the day job that paid for the studio.

  4. What does an ordinary working day look like for you?

    Why ask it

    Ask for hours, not philosophy. The answer is nearly always more mundane than admirers expect, and the mundane part is the part you can actually learn from if you make anything yourself.

  5. Which piece was the hardest, and what made it hard?

    Why ask it

    Difficulty is specific: a technical problem, a deadline, a collaborator, a bad year. Whichever kind they name first tells you what they consider the real work, and it is rarely the part audiences focus on.

  6. How do you know when something is finished?

    Why ask it

    Everyone who makes things has a private answer to this and almost nobody is asked for it. Listen for whether finishing is a feeling, a deadline or a rule, because that distinction shapes their whole body of work.

  7. What do you do on the days when it is not working?

    Why ask it

    The useful answers are procedural rather than inspirational. If they describe a specific habit, a walk, a different room, a smaller task, you have something you can borrow tomorrow.

  8. What did you cut from something that you still think about?

    Why ask it

    Cut material haunts people. It also reveals the version of the work they wanted to make, which is often a step or two ahead of what the audience has seen.

  9. Is there a piece people consistently misread?

    Why ask it

    This one tends to open them up because it is a small, permitted complaint. Follow up by asking whether they have made peace with the misreading or kept trying to correct it in later work.

  10. Whose work do you keep going back to, and what do you take from it?

    Why ask it

    The second half saves the question. Anyone can list influences; the borrowed thing is the interesting part, and it is often technical rather than thematic.

  11. What tool or material would you not give up?

    Why ask it

    Attachment to a specific instrument, brush, film stock or piece of software usually comes with a story about a period in their life. It is also a rare question they can answer with real pleasure.

  12. What did you have to learn that has nothing to do with making the work?

    Why ask it

    Contracts, lighting a room, shipping crates, tax, saying no. Established artists have a long list here, and they almost never get asked about it despite it being half the job.

  13. How did you pay for this before it paid for itself?

    Why ask it

    Ask plainly and do not be embarrassed by it. The honest answers vary enormously, from other jobs to family support to years of debt, and hearing the real version corrects a lot of quiet misapprehension about how careers happen.

  14. Has knowing your audience changed what you make?

    Why ask it

    A live wire, asked respectfully. Watch for whether they talk about self-censoring, about the pull toward repeating a hit, or about deliberately making something that would lose people.

  15. What is the worst advice you took seriously?

    Why ask it

    Better than asking for advice. It gets you a story about a specific bad year rather than a maxim, and it usually reveals which authority figure they were trying to please at the time.

  16. What do you make that you never show anyone?

    Why ask it

    Almost everyone has a private practice: sketchbooks, demos, writing, a whole other medium. It is where they are allowed to be bad, and where the next direction usually starts.

  17. Which part of the job do you actually dislike?

    Why ask it

    Ask it lightly. The complaint they choose tells you what their life is really made of, and it also signals you are talking to them as a working person rather than as a shrine.

  18. What would you make if none of it had to sell?

    Why ask it

    Only ask this if the conversation has warmth in it, because it can sound like an accusation. When it lands, it produces the description of a project they have been carrying for years.

  19. What do you want to make that you cannot do yet?

    Why ask it

    The gap between ambition and current skill is the thing working artists think about most and discuss least. The answer often names a technique, a scale or a collaborator they are still trying to reach.

  20. When someone sees your work for the first time, what do you hope they notice before anything else?

    Why ask it

    A good closer because it hands them the last word and it is specific enough to answer honestly. If they name a detail rather than a feeling, you have just been told where to look next time.

Talking to someone whose work you love

Practical guidance for the conversation itself

If you have thirty seconds

  1. 1Say one true, specific sentence about the work. Name the piece and the detail, not the whole catalogue.
  2. 2Ask one question, not three. People in signing lines ask three and get a polite answer to none of them.
  3. 3Pick a question that can be answered in a sentence: the hardest piece, the one they still like, the tool they will not give up.
  4. 4Do not ask them to explain their meaning, evaluate your work, or settle a debate you had with a friend.
  5. 5Thank them and move. Being the person who did not hold up the line is its own kind of respect.

Questions they have already answered a hundred times

  • Where do you get your ideas. Swap for: what were you making right before the work I know you for.
  • What advice would you give a beginner. Swap for: what is the worst advice you took seriously.
  • Who are your influences. Swap for: whose work do you keep going back to, and what do you take from it.
  • What does this piece mean. Swap for: is there a piece people consistently misread.
  • Are you working on anything new. Swap for: what do you make that you never show anyone.

If you get a real conversation

  • Follow the answer, not your list. The question you did not plan is usually the one that gets somewhere.
  • Ask about process before meaning. People talk more freely about how than about why, and the why tends to arrive on its own.
  • Let silences sit for a beat. Thoughtful people take a moment, and filling the gap with a second question ends the good answer before it starts.
  • Notice when a topic closes. If an answer gets short and general twice in a row, move on rather than pressing.
  • If you are recording or posting anything, ask first, including for a studio visit or a private aside.