I reckon the best way to have empathy with your model is to test things on yourself. I’ve always believed that the eyes should be the focal point of your portrait and when capturing a headshot it’s important to inject a huge helping of your personality into the shot. That’s why developing a great rapport with your client is definitely key to capturing them being themselves. There’s lots of stuff written about posing and for clients who find that difficult I like to use the “strike a pose” app on my iPhone. It can certainly break down barriers and really helped me out when I photographed two sisters recently. Check out Peter Hurley’s advice on what you should do with your eyes and see what you think.
I have to say I had a go at squinting and I think it made me look a bit scary. Check out my examples and see if you can work out which image reflects the real me. I’ll give you a clue – its not squinchy me in the middle.