While attending Syracuse University's photojournalism program, one of our professors gave us an assignment, go out and shoot four rolls of 36 exposure film, (yea…I’m dating myself) 144 pictures of people, but, the clincher was we could only photograph the subject with a 50mm lens and only shoot that individual once. So, we had to shoot 144 different people. That's one way to break one's shyness.
Photographing strangers requires being sensitive. People, especially in this day and age, don't like having a camera stuck in their faces. Instead, try to calm suspicion. Introduce yourself and communicate in a sincere way why you want to make a photograph of them-because you're interested in what they are doing. Once you make that connection as a human being, most people are flattered by your interest and open up to you. Also your body language can do the trick: There's no cultural barrier to a smile or expressing your admiration for a pretty child.
My style is to surround people in their environment with things that make them different from other people. When you go into someone's environment to shoot a portrait, there is something around the subject that makes them special. Everybody has something that is symbolic of what they do. To establish a working relationship with the subject, ask them to explain what they do. That gets them relaxed, while at the same time, gives you ideas for pictures.
When shooting people I like to travel light and use my 16-35mm, 28mm-70mm and 70-200mm zoom lenses. One of the keys to successful people photography is the ability to work quickly when needed. And the zoom lenses help me do that: I can compose my scene, and then “shoot and move to another angle.”