Taking great portraits is as much about people skills as it is about technical ability, or using the latest and greatest photographic equipment. Sure, refining your technical skills and knowledge may expand the extent of your capabilities, and using superior equipment may indeed boost your edge. But, unless you can first see through your subject's eyes, and understand her as a unique individual, and then build rapport with her so you can unveil and accentuate her finest qualities, your portraits will remain mediocre at best. Some lessons learned along my journey as a photographer may help those who choose to follow.
1. If using a tripod, compose your portrait and then take one step just to the side and forward from the camera. Do not look through the viewfinder as you capture your subject's image. This allows you to make eye contact initially with your subject, and then direct her in mood, expression, position, and the angle of gaze you are aiming for. When your subject interacts with your camera, the result can be a cold or lifeless rendering, but when you engage your subject through eye contact, expression, gestures and words, the result can be a warm and candid reflection, charged with mood or emotion.
2. If you are not using a tripod, you really should redouble your effort to maintain constant interaction with your subject. Many photographers tend to keep their eyes in the viewfinder of the camera, but this leads to your subject interacting more with the front glass in your lens than with you. Again, you do not want the sterile and lifeless rendering that most often comes when the camera serves to isolate you the photographer from your subject. Interaction with an inanimate object (your camera) can never be a substitute for interaction with another human being (you), when your goal is to capture the essence of your subject, and reflect the attitude and emotion she was feeling at that moment in time.
3. Allow your subject to be herself. A little girl dressed up in fairy wings for a special picture is very cute, and I suppose there is a place in this world for cute. But, contrast this with the little girl who just loves to dance. You put her in her everyday clothes, stand her in front of a plain backdrop, put on her favorite music and say to her, "can you show me how to dance to this song?" You should have no difficulty in capturing timeless expressions there. Now imagine a jeans and t-shirt kind of guy whose true passion in all of life is sailing. You dress him up in a tailored suit; formally pose him in front of a low key backdrop, seated in a Chippendale chair, and use classic loop lighting. What would be said of this portrait years later? "Who was this guy, an executive?" But just suppose, you photographed this same guy in his favorite t-shirt and blue jeans, at the helm of his beloved sail boat, on a beautiful late afternoon, just as the boat was coming about? What would be said of this portrait years later? "This was Charlie, doing what he loved most! That was such a glorious day." The point is, "keep it honest". Fantasy can be cute, but your subject being herself, years later this will be much more meaningful.