1. Put the focus on the thing in the background, not them
I like to say,
“Excuse me, do you mind if I made a portrait of you and that sign in the background? I think it would make a really cool photograph.”
This calms people, because the focus goes on the background, not them.
2. Compliment your subject
Tell them why you want to make a photo of them. Is it their look, their hair, or style?
Put the emphasis on why you want to photograph them:
Excuse me, I absolutely love your red hair and look. Do you mind if I made a really quick portrait of you, your red hair, against this background?
3. Direct your subject
Don’t be shy. Interact with your subjects and ask them to pose for you!
If someone is smoking a cigar, ask them to keep smoking it, and to blow the smoke into your face/camera.
You can ask your subject to look down, look up, or directly into the lens!
4. Wait for your subject to enter the frame
Pre-compose what you consider an interesting background, then wait for them to enter and shoot. Pretend you’re shooting the background behind them.
5. Tell your subjects not to smile
You can “cheat” by telling your subjects NOT to smile, like the shot above.
6. Play the “tourist” card
Also another tip:
Pretend, or tell your subjects that you’re a tourist.
This way, people give less flack to tourists.
7. Ask for permission
When in doubt, ask for permission to make a portrait of them. At worst case scenario, they will say no. At best, they will say yes!
8. Talk to your subjects while you’re photographing them
You can say (while shooting):
“You look like a lovely family.”
You don’t need to ask for permission. Just start shooting, and talk to your subjects while photographing them.
9. Start shooting before thinking
Hesitation is death in street photography (and life).
Overcome hesitation by allowing yourself to simply react to whatever you’re seeing, and start shooting.
Worry less about composition, more on just shooting.
10. Photograph people behind windows
If you photograph people behind windows, they cannot run after you. Thus, shoot people behind windows, smile, and wave at them after photographing them, and move on.
99% of street photography is courage.
Have heart in yourself, think less, and shoot openly. Recognize you’re not doing anything wrong. You’re documenting the beautiful social world in which we’re living in. This is your duty.
Just shoot it.