The thing that intrigues me the most about taking headshots is the challenge it presents. You have just ONE photo to capture a persons story, their personality, and character. In say something like a wedding, you have the entire day, various events, several settings and props which ultimately gives you a good number of images to tell the story; where as in a headshot you've just got one. While in a headshot session you may take many photographs however, all you really have to work with is the subjects face for the most part. The photos below were taken at work of some new hires within a 30min period. I plan on purchasing Peter Hurley's Art Behind The Headshot dvd later this year and following up this post with some new learning and discoveries.
*shoot notes
Shot this in the corner of a fairly large room with white walls. Behind me is a decent sized window, but not floor to ceiling. I used an flash that was pointed directly up for a fill light. To the right of the subject is the corner wall and to the left is a white piece of foam core. Directly in front of the subject is a white table which I used to help fill in any "under" shadows.
-w