Have you ever wanted to lose weight? These kinds of things are easier done with a friend, so you can help motivate each other. And nothing motivates a competitive person like me than a good old fashion bet. Now to add even more incentive, you can't bet on something you want to win. That's like saying if nothing changes, nothing changes. What you really need to bet is something you desperately don't want to lose.
It just so happens that my friend's a bit (understatement) camera shy. So for her, we would go shopping, and have a photo session in studio. For myself, you'll just have to imagine because I won. :)
When you think about what's important in photography, lots of different things come to mind. A good eye, and the ability to compose and image. Good technique, to create sharp, correctly exposed images. Good light and interesting shaping of the light. A good camera, lens, and other tools to help capture the image.
An often underrated skill for portrait photography is the ability to connect with the subject.
Much of the photography you see on the Web, or even on this site uses models. It's their job to deliver. But even when working with models, it's hard to get the best out of someone without establishing some rapport. For good portrait work this can be critical. The subject has to trust the photographer enough to let themselves pose unnaturally, and to put themselves out there for the shot.
Without that rapport, it can be a real challenge to get the shot.
And from the photographer's side, it's important to make room for the real person in front of the lens, and provide opportunities for that real person to come out. For my friend, it's her inability to take herself too seriously. So while we took some good shots, like the one above, the ones that really captured her personality are really more satisfying.