Family sessions seem to be either the easiest or the hardest type of shoot. Depending on the flow of the family some sessions are downright hard. Emotional connection is a large part of my work and being able to really show the personality of each family member is my ultimate goal.
Remember when you had school photos in elementary and you just knew you did your best to give the great smile you knew would make you mom proud. Meanwhile photos were being processed and returned, it only took one look for your mom to say why didn't you smile like you normally do? Kids in general don't know the different between a fake smile (the kind that your parents are always asking you to smile in family photos) OR the genuine make your heart happy smile.
Here are some tips tricks I've come up with along the years
1. Never just ask a child to smile. Chances are you are going to get a cheesy over the top grin.
2. I start by asking them to make different faces for different emotions. By now they know what a sad face looks like so I ask them to do a sad face, I then stop and photograph them, I do a silly face, photograph, angry face, photograph, and so on until I come to a happy face. By then they are relaxed and well versed in this fun little game they are playing.
3. After getting a happy face. I then act like I'm about to tickle them. Now this does not work for every child, as each child as a unique personality and set of personal boundaries. In general however most children react with a authentic and genuine grin that I try my best to capture.
All in all my best advice with family is have fun and try and make everything a game!