I'm pretty good at taking portraits of my family and friends; I know who they are and what they "really" look like. But if I'm asked to make a portrait of someone I don't know so well, I'm often unhappy with the results.
I know some tricks for getting people to be comfortable and to drop the cheesy smile, and for getting serious expressions. But beyond that, a portrait is supposed to capture the personality or essence of a subject. How do I get more than just a technically fine "picture with a person in it" when I've only got a short time with that person?
I imagine that this is something serious working photographers come up against all the time. When it's Winston Churchill (or someone else famous), one might research beforehand, or have the luck (and chutzpah) to do that cigar-stealing trick, but what about just normal strangers that I want to photograph in a single short sitting?
You've hit the hard part, all right. And there is a distinct difference between shooting celebrities and cultural icons and shooting "real people". How many of Churchill's friends would have looked at Karsh's masterpiece and said (in today's vernacular), "that's so-o-o Winnie!!!" But it was very much the way the world needed to see Winston Churchill at the time, so if he only ever looked like that when someone had stolen his stogey or hidden his Scotch, it really didn't matter. He was an icon, and that portrait was an icon of the icon. In the same way, nobody wanted to know, really, what Archie Leach or Norma Jeane Baker looked like, they wanted pictures of Cary Grant and Marilyn Monroe.
When you're dealing with "real people", it's difficult to imagine ahead of time what that picture is going to look like. And it doesn't help at all that you are hampered by what sociologists call the Observer's Paradox — sticking a camera (or microphone, or even a notebook) in somebody's face and saying "don't mind me, just act normal," almost always has the opposite effect, at least in the short term. But you're not after the Daguerreotype look (a technically perfect picture lacking life altogether), nor is this a model shoot. You don't want people looking at the picture and saying, "that looks just like George," you want them saying, "that's so-o-o George!!!" The shot can be perfectly lit and executed, and can have a "great expression" and still be a failure as a portrait. You want an iconic representation of that person; someone their friends and family would have recognised from behind at a distance at night on a crowded sidewalk, to stretch a metaphor slightly.
That takes engagement on a personal level. Ideally, you'd want to have a bit of a pre-photo-session session with them, but that's not always possible. Let's assume, though, that you have something more to work with than the poor buggers who do school pictures (two a minute at least — "sit on the stool, 'assume the pose' and smile" is all the time you get for two exposures per kid). You can train yourself to be "intuitive", but it takes time and practice. (I started out life with something on the autism spectrum, and that led to some major problems that made staying that way untenable. People tend to mistake me for a sympathetic "people person" now, despite the fact that I'd rather be solitary almost all of the time.) Start with good body language and cold-reading techniques books. There's no need to make a study of it; just get the gist. If you can get them talking about themselves on any level, you can steer them deeper into their real lives, and they will become "real people". And you can get that transition from "client" to "person" down to just a few minutes with a little practice.
If you haven't had the chance yet, I'd suggest looking at Peter Hurley's videos as a sort of a rough guide. Most of the magic happens during the first "look" of his sessions, where the subject is minimally made up and simply dressed. (Later looks stretch people out of the everyday. These are, after all, actors' headshots and need to show who they can be as much as who they are. The first look is probably closest to who they are in everyday life.) You might not have half an hour at your disposal, but you can work in a bit of banter — and the disarmament tools are priceless.
This is a lot easier if it's a group portrait because you can get them to interact with each other and see what they bring out in each other, but really, it comes down to people skills. Getting them comfortable enough that they let their guard down and being perceptive enough to quickly learn about who they are from how they interact. Figure that out correctly and you will be able to get what you're looking for.
Wedding photography is actually a great way to learn this skill if you get a chance to work second (or third) camera for one. You get a longer time to see people in a comfortable environment and see how they relax and what makes them tick. How do they celebrate, how do they hold themselves, how do they dance? What is their sense of humor? These are all little things that you can figure out pretty quickly in a setting like a wedding and then you use that to capture their attitude.
As you get more adept at it, you can even start doing things like altering your composition and shooting style to meet their views. For a stoic, rigid person, strong, standard documentary type shots (or perhaps fine art style) is probably going to fit what they want for the collection of photos as a whole. If they are fun and playful, going more casual artistic and fun with the style is going to capture what they will think is good.
Studio portraits are of course a lot trickier since you have less time to make a judgement about them, but interact with them. The principals are still the same and it will help them relax and give your more material to work with. You can also always try taking photos to emphasize a couple of different traits and see which they prefer to refine it if you're really stuck.
For me capturing the essence of someone in a portrait is a challenge. Sometimes I'm successful and sometimes not. Currently working on a portrait project this subject of capturing "essence" came up front and center. Fortunately, I have known many of my portrait subjects as friends or associates. One would think that advantage would make the job easier. Not necessarily. Instead of just a friend, I'm now someone behind a scary camera, and they are often not warm to be photographed.
My plan is to photograph my subjects in their own element...where they feel most comfortable versus them coming to my studio. After studying the work of Arnold Newman, I could see the benefit of this approach. Using available lighting also seems to keep subjects relaxed. Not using lights helps them to not feeling like they are under a microscope. Talking about their projects, plans, and life in general allowed me to watch their faces and bodily movements to see how they responded to my inquiries about their lives and work.
My work flow is to start out using my digital camera to get them used to the idea of being photographed. It is also the time I use to scope out a design to use. Once I sense they are becoming more relaxed, I bring out my large format camera. Since I take some time to set up, this is a wonderful time for them to explore their curiosity about my work process and equipment. The tables are turned. They relax more. As I proceed to get my equipment ready (I'm kind of slow and can be a bit of a klutz.), they sometimes become a little bored. Bingo! That is where I want them and I begin to make images. My best images come toward the end of the photo shoot.
Check out Strobist's Lighting in Layers. There's lots of great instruction on using and controlling light, of course, but there's also a great deal of insight to how he works with a subject to get such great expressions. Very informative for just your purpose, I think!
What I do is I pay close attention to their face, their expressions, and their mannerisms. I observe for a while. Soak up the vibe. See what makes them who they are. Everyone is special and different. Then, when I look through the lens, I'm able to better make the split-second decision of "Does this moment right now capture that person's personality?"
In terms of live-music photography, I always prefer to go listen to a band play before ever picking up the camera and shooting them. I've found watching closely is just be best way for me to prepare.
If crunched for time, I have to rely on past experience with other people who might have similar attributes, which is, in essence, relying on a vast database encoded in a gray-matter neural network.
The more people you observe and photograph, the easier it becomes to capture in a photograph. As a bonus, you learn to observe people more closely in general.
It just happens to be the opposite for me, it becomes murch harder for me to portrait close family members.
But when I'm with "strangers" what I do is not making such a great deal with the shooting. I say, "this is just a test" (the first shots actually are) but then I never say "Ok, this is a real one", I simply make a natural transition from adjustment confirmation to real shooting without anouncing it.
In the time beetween shots, I make some non-prefabricated small talk, to connect with the client without getting too personal, being empathetic and non judgemental.
I also take little pauses while faking to stop paying attention to the portraitee. I pretend to review pictures in the camera, or check something in the equipment, but in relity, I pay close attention to their natural poses and gestures. After that, I tell them: "you took this posture" or "you laughed this way" and proceed to reproduce that, but this time sooting, making sure to tell them that the pose is coming from them.
It works pretty well on most subjects, because I'm not forcing them into postures or gestures they don't ussually make. I fisrt shot "as is" assesing the shot only at a glance in the camera's lcd. Then I improve the pose by making just small adjustments.
In the middle of that, take some unanounced shots when the client makes this "poses of their own". Do it quietly and don´t let them see you asessing the shot right after you took it, review it later.
In order to boost their comfidence, I show them a few shots quickly, only the ones I think are really good and only for a few seconds. Also I try my best to keep a "this is really good" face and not showing dissapointment if a shot is not perfect or something goes sligtly wrong. (A few days ago, for example, during a shot, one of my strobes misfired, I didn't make a deal out of it, and continued shooting. When I cheked in post, It just happens that the shot was perfectly good, albeit in a diferent mood bacause of the lighting. I simply processed it accordingly).
To put it briefly, I play a bit of a psychoanalyst, and try my best for the client to feel comfortable and comfident, so their personality comes to surface. It works almost with every one, with some quicker than others. Sometimes allowing the presence of a family member or close friend or co-worker may help if that person happens to be a confident booster for the protraitee, but if they to the opposite, take them out of the room ASAP.
Your own attitude plays a big role too. Being comfident and positive yourself relieves part of the scenic stress for the client. Do not let it show if you are in a rush, or if you are concerned with something else.