Feel the fear and do it anyway
Asking people you don’t know if you can take their picture can be quite nerve racking. It could be a fear of rejection imagining all the terrible things they could say, but in reality the fear is usually worse than the actual rejection itself. If someone refuses then it’s usually just a polite, ‘No thanks’. I’ve never encountered anybody who was angry or annoyed by me asking. I still feel nervous sometimes, but the more you do it the easier it gets. A surprising fact is that a lot of people will actually say yes (about 90 per cent).
For street portraits, approach subjects with a big, friendly smile and be polite and confident. When I ask someone if I can take their picture, I often pick out the thing that drew me to them in the first place; it gives me a place to start building a conversation from. Maybe they have a cool style, a nice hat, a beautiful smile, or a great face; keep it positive, as everyone loves a compliment. I often used to say that I was studying street photography and doing a project about whatever fits the person. More people than you might imagine are glad to help when they believe they are helping someone, and by approaching them in the right way you have already built a bit of a relationship.
Look for suitable backgrounds and light
Now that you’ve got your willing subject in front of you, quickly assess your surroundings to choose the most suitable background and be aware of available light for the shot. It’s easy in the excitement to forget about the technical side of street photography. So if possible, consider the lighting and the background before even making the initial approach. Sometimes I might ask the subject to move into a better background or light situation, but don’t push people’s patience too far.
Build a rapport
Keeping a conversation going for a while and building trust between you and the subject on the street is almost always going to result in a better photo. If you keep a conversation going, you may even be able to ask him or her to move to a better location or area of light. Pointing a camera in somebody’s face without any kind of rapport is unlikely to result in great shots – unless you are Bruce Gilden. While you don’t need grinning portraits, you don’t want annoyance showing in the eyes of the subject, either.
Don’t conform to rules
There is no rule that you must take a candid photograph for it to qualify as street photography. Many of the subjects shot by the best contemporary street photographers are fully aware they are having their photograph taken. Some street photographers fully engage with their subjects in order to make a striking and more powerful image. There’s no need to sneak around or find the nearest bush to linger in. Often, you may be spotted but your subject may simply look away. It also helps to be quick in these situations. If you hesitate too long, you may get eye contact where you simply don’t want it. Sometimes eye contact can kill a shot, and sometimes it can help lift the frame.