Picking the shots to invest in
I have seen MANY actors and actresses pick images for the wrong reasons and not get results. I have seen many of them go through the proper steps and get tons of work based off of them doing the proper steps to get a headshot that really works.
I have rarely met the person who is not at all critical of themselves when they are looking at photos. So, when you are looking at the shots from the photo session the first thing you do is take note of the images that grab you. Then you go through and find images that communicate to the viewer. This is perhaps the most difficult thing to determine. Most photographers will give you an idea of the shots that they like best. Photographers have a very trained eye, so I would recommend talking to your photographer to help you pick out the images to survey.
When selecting your shot you are looking for the shot that will stop people. More specifically, you are looking for the shot that will STOP casting directors, agents, producers & directors. That is what you are looking for. So survey your shots with that in mind.
I took photos of an actress and so many of the shots came out great that she did not quite know what to select. There was a shot in particular that she debated on quite a bit. It was a little dark and moody for her but the shot really impinged. We went through together and selected the top 15 shots and had them printed on 4 x 5 cards. We numbered the back of each one and then she went out to survey.
What she did was pass the stack to whomever she was surveying. She would shut up and watch them! She noted down 2 things. 1) Which shots did people pause at? And 2) which shots did people say they liked best?
The super interesting thing is that nearly EVERY PERSON she surveyed would take a long pause on this somewhat moody shot. A lot of people would comment on the moody shot saying that they really liked that shot. Most were torn between two or three shots. Survey by voice said a different shot. Survey by pause selected the moodier shot. This actress decided to print up both. A few months later I was invited to a play that she was starring in (landed by moody shot). She said that the moody one got her into so many auditions that she doesn't even send out the other shot anymore.
The moral of this story is to look for the shot that stops people. A casting director looks at hundreds of headshots. Get the shot that STOPS them and makes them actually look. Spend the money for the 4x5's of your favorite shots. Number them. Pass them to people and take note of what they STOP at and what they like. Print what receives the highest reviews on both.
Also take note here that technology has really changed with the advent of the Internet. You can sign up with sights like www.myactingsite.com and post as many photos of yourself that you choose. That way you can print up two or three shots for submittal and you can post dozens of shots showing your diversity and range. This is an especially good tool for the character actor.