Chris Sorensen
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It's SorensEn. 
Jefferies post and Jeff's link have some great info. Open shade is your friend. Shoot fairly wide open and longish (85-105 IMO, longer than that and you start to lose your connection with the actor.) But checking out your site, you know this already and have all the skill necessary to take good headshots. Definitely shoot natural light which you obviously have an affinity for. Besides Peter Hurley, pretty much every NYC headshot photographer shoots natural light and actors usually want it. (And +1 to Jeff's comments on Peter Hurley. I just shot a Peter client as well.)
Jefferies comment on the eyes and a relaxed natural pose being key to a good headshot are 100% correct. Add personality to those and you have a great headshot. I disagree that a long sleeve shirt is required. Most of the time you don't even see much of the arms, and if you do, all the fabric and color of a long sleeve can make a the bottom of the frame seem 'heavy' for lack of a better term. IMO. Form-fitting (though not tight) is almost always better than loose which makes people look big. And bright colors can work, but be careful that it doesn't cross over into distracting. And black can work great depending on the skin tone and hair color. White and busy patterns are two things that rarely work. But have them bring multiple options so that you can be confident of finding something that works well on camera, and so you can shoot a few looks so they have options.
Also, the sitting in a chair or on the floor thing is not for every actor and I wouldn't try to pigeonhole every actor into those poses. While some people can be natural in any pose, some people are more relaxed standing, some leaning against a wall, some sitting, some on the ground. Try different things to a) to see which ones work best, and b) give your actor variety. And personally, I don't like solid backgrounds, looks too plain and studio-esque. I like them in an environment, though an environment with a non-distracting OOF background.
Jefferies is right about cropping into the hair. It's not popular here, but pretty much every good headshot photogrpaher I know crops into the hair. The focus is on the actor and the eyes, and leaving headroom in a pic is a waste of space. As long as you can see the hair color, style and general length, you have enough hair info in the pic. Never crop right on the hairline though, always in the hair.
On the smiling issue, you do want some smiling, but not all. Headshots come in two varieties, commercial and legit (NYC)/theatrical (LA). Commercial is typically smiling or at least lighter in tone than the legit/theatrical shot. Legit shots don't have to be all dramatic and serious though, it depends on the actor's type. Some are serious, but a girl-next-door's might be sweet, the nerdy guy's could be quirky, the sexpot's flirtatious, etc. The important thing is that their personality comes through.
You can check out examples of New York headshot photographers' work at the link below. (Reproduction is the largest headshot printer in NY and LA.) Some of the better known and popular ones on the link are Deborah Lopez, Chia Messina, Jeremy Folmer, Hoeberman Studio, Leslie Hassler.
www.reproductions.com/NYC/2008/
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