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Variation is key. You need to walk away from your session with a good selection of cropped (shoulders up) pics that show different expressions (plain, smiling, sassy, sombre, sympathetic etc). This variation also means that if you have long hair, make sure it's both up, down, ponytailed, swept to the side etc.
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Smiling is important for a casting director to see your teeth. They may be crooked, stained or you are wearing braces so you absolutely need to make sure these are in one of them.
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If you will always wear glasses then fine, but generally, headshots should be without them. It's harder to light a picture with reflections from a key light. Make sure you remove them an hour before the shoot to avoid indentations.
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Please pay attention to your skin. While most imperfections can be removed in Photoshop (particularly non-permanent things like a spot), it's a harder job to remove dry skin, stray hairs and so on. Moisturise before your session. Hydrate. Look at yourself close up in a magnifying mirror and tidy eyebrows, facial hair and use a chapstick. If shaving, don't do it an hour before the shoot! Ask someone to check around for any missed patches.
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If you normally wear a lot of makeup, make sure you have at least one shot without it. And don't go overboard. Mr. Snuffleupagus and tons of foundation isn't a natural look.
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Avoid bright high contrast or coloured clothing (white, yellow etc). Keep it to one colour. Garish colours can often tint colour correction later. Turn up with a selection of tops (3 minimum) and avoid any labels. Make sure they are wrinkle and dust free!
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Remember, headshots aren’t portraits – they represent you as a performer so they should follow three simple rules a) They should ensure that you connect with the casting director, in terms of suitability for the role by expression and demeanour. b) They should show a variation in pose and attitude. c) They should be natural and represent you in real life.
The points above should help you with good preparation and also act as checklist to ensure that you get the best out of the session.
Good luck!