begin with the end in mind
Too often, a portrait is simply a picture of a smiling face. Pleasant enough to look at, but unfocused in its intention and therefore less likely to properly fulfill any given purpose. Ideally, a portrait should be made with the end purpose in mind. The visual language of an image will vary depending on the intended use. For what, exactly, do you need images? One purpose? Several? This informs and directs the process. Whether you want something for professional applications, online dating, social media, or to commemorate a special time, how you'll use the images and how you want to be perceived in them will shape the images that are made.
A smarter process for superior images
I believe that maintaining a smarter process yields better results. In practical terms, this primarily means spending a little time before the photo shoot to really clarify what you want as a final product. This may sound obvious, but you'd be surprised how rarely it is done with any real depth. As previously mentioned, the final application of the images will determine a lot. But there are other factors to consider, too. For example, how do you want to be perceived in the images? Confident? Kind? Funny? Intelligent? What are the things you want to avoid in your pictures? What do you like or dislike about existing pictures of you? What are examples of portraits of other people that you especially like or dislike?
By coming to a clear understanding before the camera even comes out of the bag, the whole process gets easier for everyone involved. It becomes easier for you to relax in front of the camera, which makes it easier for me to get good images. If we know more clearly what it is we're trying to achieve, the whole process can be made more efficient. It also just plain helps ensure that the overall quality of the images is high.
If it sounds like a lot of work, don't worry. My method may require a little bit more effort from you than simply sitting and smiling while I point a camera at your face, but anything worth doing well is going to require at least a little work, and subjects often find the experience enjoyable. When you're more involved in the process, you also feel a greater sense of satisfaction with the final result, which is good for everyone.
simplicity is key
The more complex a method gets, the more likely it becomes that problems will arise. Complexity invites failure, while simplicity tends toward reliability. It's also less of a headache for everyone involved.
I like to work simply.
The process begins with a new client interview. This can be in person, over Skype, on the phone, via email, etc. It doesn't have to take too long, but it's an important step toward understanding what it is that you are looking to get as an end result. If we are on the same page from the beginning, it's a lot more likely to be a success.
How do I shoot? Typically, it's just me. No assistants or stylists (though stylists can be arranged), no equipment carts, no big lights, no huge affair to deal with. Under most circumstances, it's me, the subject, one camera, and one lens. If you want a friend to come along for moral support, that's fine, too. I work almost exclusively with existing light and prefer to shoot in settings familiar to the subject. This could be your home, your office, a local park, etc. I typically use a digital camera, but sometimes shoot on film, depending on what the client is looking for.
Why existing light?. It simplifies the process and there is great light all over the place (you just have to know how to look for it). I also find that subjects can relax more easily when there aren't big lights in their face in addition to the camera. Existing light is a key element of my overall working method and style. If you are looking for someone who is going to come in with a cart full of lighting gear and make a full production of the portrait, that's just fine, but understand that's not what I do. This leads us to the next key point.
I may or may not be the photographer for you
Working with a photographer is like working with anyone else you might collaborate with in that not every pairing is going to be a good fit. If you consider me to be someone who will come in and focus on environmental portraiture, that's a good start. If you see me as someone who you want to emulate another photographer's style, it's best that you hire that photographer instead of me. It's important to me that you get images you'll be satisfied with, and if I feel I'm not the right photographer for the job, I'll say so. But if you look at my work and like what you see, let's talk about what I might be able to do for you.