First off, what the heck is an “environmental portrait”? Sounds like you have to go out and capture someone standing next to a Redwood tree. While this could be the case, it could also be that they’re holding a chain saw.

Ansel Adams said in his book Natural-Light Photography (sadly, out of print but still available used at Amazon), an environmental portrait “reaches farther into the personality of the individual portrayed, associating him with elements suggestive of his inner qualities.”

Above are are some  examples with jazz great Chick Corea (“Spain” is on my “perfect song”  list.)

When I’m asked to take portraits I like to find a setting that brings out the personality of the subject. This definitely doesn’t mean hiding behind their desk. I look for places where they are comfortable or that put them at ease. But you may want to turn that on its head like Annie Leibovitz often does and throw in a severe contrast to bring out their personality, or throw in the unexpected like her shot of Demi Moore (I took this at her show “A Photograher’s Life” in San Francisco.)

Here’s a strong example of an environmental portrait I took many years ago in Sinaloa, Mexico. Fausto was one of the locals working on the project I was assisting on as a high school senior, building a medical dispensary deep in the Sierra Madre mountains, days travel by foot and jeep above Mazatlan. I took this with my trusty Roliflex, given to me by my Uncle Sambo

Here’s what I suggest:

1.    Find a place that you think is a good match or even a contrast to shoot your subject.
2.    Take shots, but talk with them, engage them. Take their attention off of the camera.
3.    Don’t sit or stand in one place, move around and have them move around. You never know what magic might occur with changed light or a changed angle.
4.    Take lots of shots.
5.    Be inventive and try different spaces, angles, moods, etc.
6.    Look over your shots as you go so you can see if you’re getting what you want. Know when you have it and wrap it up. Don’t drag it out.

How’s that? Let me know how it goes.

Good shooting.