Look for a Qualified Person.
Being an artist, caricature or otherwise, is one of those rare occupational titles that doesn't actually require any official credentials. If you call yourself a Doctor, it's pretty much a given that you've gone to medical school. If you hang a shingle claiming to be a plumber, folks have a right to expect that you completed some professional training, or carry a union card that qualifies you to fit pipes that manage to keep the water on the inside of them. But being an artist is a different. It's one designation that you give yourself. You are one because you SAY you are.
So how do you know if the caricature artist you're thinking of hiring is any good? The answer is two fold. Experience and Portfolio. First, experience. There are a lot of caricature artists out there. Some are amazing, some are deluded about their ability. One great way to figure out which one you're dealing with is to look at their track record. A good caricature artist will demonstrate a solid work history, have a list of clients and be able to refer you to past clients who have hired them. Next: Portfolio. You should be able to readily view multiple, real-world samples drawn by the artist. These sample caricatures should reflect the type of work the artist does in the situation for which you are hiring him. In other words, if you are hiring the artist to work from photos, ask for samples of their "studio" work. If you are hiring a caricature artist to work at a live event, ask to see samples of the kind of work the artist would do in that situation.
Here's a tip: When reviewing a caricature artist's portfolio, don't be intimidated into feeling like you need to put on an art critic hat to "understand the motivation of the artist"...just go with the one you like! You're the expert on that! If you found this information helpful, and are looking for a High Quality Caricature Artist in Massachusetts, please consider booking The Caricature Guy http://www.thecaricatureguy.com