It can be difficult to take pictures of a person who is clearly not used to being in front of the camera, or doesn’t like being photographed at all.
And when you think about how much publicity the image is going to get, and how it’s supposed to someone look and feel professional, it’s very important that you know how to direct your client.
Have a pre-session consultation
Before your session make sure you know how the images will be used and what style they would like. This can be on the phone or face to face. Talking to them, will help them relax so much more than email. This will allow you to help them prepare for the session. Make sure they know what to expect, and are as relaxed as possible.
Create separation from the background
Make sure that your subject doesn’t stand too close to the background. If you are using a studio background (or wall in an office) and you stand someone close to it, you may see shadows on the wall, which makes the images look less professional. For environmental headshots outdoors, I still recommend separation from the background. The bokeh creates a nice nondescript background, especially when shot at a wide aperture. Typically I aim for an aperture of f/4 for environmental and natural light sessions, and f/8 for studio style sessions with lights.
A great way of helping people to relax in front of the camera, if you don’t have much time with them, is to ask them to pull a funny face for the first frame. Use this as a lighting test for a new person as well. This is great at breaking the ice, and very few refuse to do it. Once they have pulled a daft face, everything else is easy!
It’s all about the little adjustments
What separates a great headshot from an average one, are generally very small changes. These little adjustments can make all the difference. The slight tilt to the head, leaning forward, a gentle but intriguing smile. Don’t be afraid to ask someone to make very specific changes to their expression and position, until you get the image you’re looking for.
Keep talking and be positive
When you’re in the midst of taking photographs, make sure that you keep talking to your subject. Reassure them that they’re doing it right, and you’re getting great images. Even if you’re not satisfied with the images when someone turns their head in a certain direction, or how the light is falling on them, never express that to your subject. Silence will kill the atmosphere, so no matter what is happening, just keep chatting and being positive.
Source: Digital Photography School