Three questions to ask before commissioning a portrait

Portraits are different from other commissions. A landscape can be hung in any room and appreciated by anyone. A portrait is about a specific person — usually you, or someone you love. The stakes are higher. The wrong portrait is a permanent reminder of the wrong decision.

If you are considering commissioning a portrait — of yourself, a partner, a child, a parent — here are the three questions to ask yourself first. The answers will shape the brief and (more importantly) tell you whether you're ready to commission at all.

Question 1 — Whose portrait is it, really?

This sounds like a stupid question. You said "a portrait of my mother," and you meant a portrait of your mother. But whose portrait is it really?

If the portrait is for you, then it should please you. The subject's opinion is secondary. (This is the simplest case — most portrait commissions fall here.)

If the portrait is for the subject (a gift, for example), then it should please them. Your opinion is secondary. This is harder, because you have to predict what the subject will like. Some subjects have strong opinions about how they look (most do). Some don't care about the painting and will love whatever you give them (rare). Most are somewhere in between.

If the portrait is for both of you, then you have to find a balance. This is the hardest case. The brief has to be carefully worded to satisfy both viewers. Talk to the subject first, if possible, and ask what they would want. The surprise of a portrait gift is overrated — most subjects are happier when they have input.

Question 2 — How long should this painting last?

Oil paintings last hundreds of years with basic care. Acrylics last decades. Watercolours last a generation if framed behind glass. Digital concepts last as long as your hard drive.

Most portraits commissioned through gestuo are originals (oil or acrylic). The price reflects the longevity. A digital concept portrait is cheaper but you cannot pass it to your grandchildren. Decide how long you want this painting to exist, and that will narrow your tier choice.

Question 3 — How much of yourself should be in it?

This is the question most people skip. The answer matters more than you think.

A photorealistic portrait of your mother, drawn from a single reference photograph, is largely a technical exercise. The artist's hand is visible in the brushwork and the colour, but the composition is dictated by the photograph.

An interpretive portrait — your mother surrounded by the plants from her garden, lit by the lamp she reads by, captured in the moment you most remember — is a collaboration. The artist is interpreting your memory as much as your mother's face.

Neither is better. They are different commissions. Decide which one you want before you write the brief. If you want the latter, plan to spend more time on the brief and to have more back-and-forth with the artist during the work.

Once you have answers.

When you have answers to all three, you are ready to commission. Write the brief in your own words. If the subject of the portrait can read the brief, let them. The clearer everyone is upfront, the better the result.

And if you're stuck, use gestuo's AI brief wizard. It asks the right questions in the right order, and the output is editable. You are never locked in.