Of course something like this is pretty ridiculous to imagine but you’d be shocked to know that it happens all the time. And even more ridiculous is that it sometimes gets results.
Why? Well, portraiture is a psychology game. You can’t often tell someone to smile but instead you need to make them want to smile. It has to be genuine and when that comes out then it starts to make more sense on camera. Lots of people are often intimidated by the camera and finding a way to distract them works: kind of like what you have to do with dogs. Of course this also varies at times and in each situation. I’ve seen people fall head over heels for big old vintage cameras because it’s something so cool and different vs the more traditional SLR style cameras. But if you don’t have the luxury of rolling a 20×24 camera into your apartment, then you need to shoot smarter.
Another great tip, talk with the person, get to know them, and take your time to relax. Once that gets done then you can figure out a way to make taking headshots even easier for both of you.