When you get your proofs from your photographer, show them to a few friends and family for their opinion on what looks the most like you. The way you see yourself is not how others see you. I’d also show your proofs to a few people who don’t know you as well. They will give you an unbiased opinion just based on how your everyday look compares to your headshot. Once you’ve collected everyone’s views on your pictures, discuss your top 5 with your photographer. They can give you a perspective from a technical view about which ones look the best. Take everything into account before making your decision. Remember, it is your decision, so don’t choose a photo you hate because everyone else loves it. Ultimately you need to be happy with how you represent yourself.
What do you want your headshot to look like? YOU! Not a supermodel version of you. The main focus should be your eyes, followed by your appearance. Your picture should capture your presence and personality. When someone chooses to meet you after looking at your picture, they shouldn’t feel surprised when you walk in the door.