When Chris gave the OK for our session, there was one stipulation: 'Promise me no one will see the images'. Yikes! Confidence was low and so were his expectations, but I gave him my assurance no one would see the images.
I knew he was reluctant to go straight into a headshot session so I had him bring one of his guitars. I decided we could shoot some of him playing, he could get lost in the guitar and forget about the camera. Every so often I would show him the view screen and he liked what he saw. Confidence rose and the comfort level rose and we segued to the tighter headshot session without a hitch.
If your photographer is not a good fit, choose someone who is. Great images resulting from a poor experience is a rare event. Have fun!
Say hi to Chris - a financial risk manager from Toronto. I think we managed the risk quite well.