Here are some steps you should take when you are choosing your headshots photographer. First, find someone you believe you will be comfortable with. I strongly think that being able to develop a strong rapport with a photographer, to really “hit it off” with them, makes all the difference in the world in how your headshots will come out. When you are comfortable and loving what you are doing, you will find it much easier to project yourself to the camera with a confident, positive, and comfortable aura. You will also be far more likely with experimentation: trying different looks, different facial expressions, and so forth. These experiments can lead to a unique, eye-catching, and outstanding headshot, but you have to be comfortable with the photographer to try it. When you are comfortable, your smile will be genuine, not fake, and your overall expressions will come to life much more than if you aren’t comfortable.
Second, look for a headshots photographer who has a portfolio with quality, professional-looking headshots done in a style that you enjoy and would feel comfortable working with. I don’t think I have to say that you need to actually like the work of the photographer you decide to work with, but I’ll say it anyways. You might not be a great judge of what makes a perfect headshot, but you should at least be able to recognize that you like your photographer’s work. If not, what’s the point in hiring that photographer?