The first time I did any large scale portraiture shoot was several years ago when I told my children that for Mother's Day all I wanted was for us to go to the beach so I could take some pictures of them. I don't know if I caught them at a moment of weakness or that the promise of lunch at BJ's at no cost to them on Mother's Day was appealing, but they acquiesced without any complaint.
I had some ideas of what I wanted to do and I printed out some ideas that I had seen online as reminders to myself in the event that I lost my vision as soon as I put the camera up to my eye (which is not uncommon for me). As we finished up our desert, this voice inside my head told me to share the pictures with my family and tell them what I wanted from them once we got down by the water. It was the best thing I could have ever done. The whole time, things flowed pretty easily. I wish I could say everything has been simple ever since.
I guess my point is this. If you do have a vision for the pictures you want to take, you have to share the vision before you start taking the photos so your subjects have some idea of what you want them to do. I'll guarantee you this...if you don't, they won't miraculously know what to do and you may end up disappointed. And if you don't have a vision? Well, you may be lucky and end up with some good shots, but I wouldn't want to count on luck every time I go out shooting. It helps to have a vision.
In addition to vision, you need to be able to be specific and look at all aspects of the shot in the frame. This is where perfection counts more than anything else. In the picture below, a good shot was ruined when I didn't notice that I was capturing part of the door in the background.
Look at the shadows falling over the face, look at how the background is flattening out, look at the placement of your subjects in the frame, take time to determine what is going to stay in the frame and what will be outside of the frame.
As you get flowing and the trust builds between you and your subjects, you'll find that things naturally flow from one thing to another. My biggest problem is that I have a hard time directing everyone and I'm not good at recommending poses. I'm trying to take more control than I have in the past. Sometimes it's easier than others.
If we're outdoors, one of the best tricks that I've learned is having your subject(s) walk towards you.
When trying this out, stand as far back as you can as because usually when they start walking towards you the first few steps are likely going to be awkward, but the more steps they take, the more natural the shots you get because somewhere along the way, they start laughing about the whole thing.
This is one of my go to, works every time, tricks.
You just have to make sure to remember to keep adjusting the camera down so you don't cut your subjects at the ankles, ruining an otherwise perfect good shot.
When shooting group shots try as much as possible to mix things up. Instead of your typically, facing the camera, think of new ways to capture everyone.
If something isn't working, let it go and move on. There is a lovely brick bridge off the freeway on the way to my brother's house. As soon as I saw it, I knew I wanted to take some pictures there and one evening Brie agreed to go with me.
What I wasn't prepared for was the amount of traffic whizzing by in the evening hour. Brie's attitude quickly began to change especially when several cars honked at us. I had to let go of the ideas I had because she was so uncomfortable. We ended up going to downtown Vicksburg and had a good time taking pictures there.
Have tried and true things to pull out of your back pocket. If a person or persons can't relax, have them make faces at the camera. Sometimes that works, but there are times this can backfire if there are little children involved. Sometimes just talking to them about how great they are doing (even if they're not) can help get them to relax.
In the end, I think I've learned that it takes a LOT of practice to get good portraits go out as often as you can to hone this skill.