When my son's pre-k (what they call pre-kindergarten here in the states) teacher asked for a recent family photo I knew we had to do one up the one from last year.
I sat down with my sketch book and created 4 or 5 really awesome concepts that I thought would be fun to photograph and process... after all, if this becomes a chore it defeats the purpose right? In the end we decided to make a photograph around my sons favorite toy, a colonial era brick fort... we just switched out the Red Coats and Yankee soldiers for fairies, goblins and lost boys.
I photographed the fort first, and placed markers where I though each of us would be located in the final image. This helped me determine the right perspective, light and shadow placement. Once we had a good plan together, I had each family member stand in and do several poses, screams and attach motions. For the boys I positioned the camera above our heads to give the illusion that you were looking down on us and for the girls I laid on the floor and had them stand on a crate so it looked like you were looking up at them. Once we had all of the photos that we needed I loaded them all into Photoshop and extracted each character from their background, matched color, brightness and sharpness. You can watch that whole process here:
It took me about an hour and half to photograph the fort and each character in costume and another 5 or 6 hours in post processing. The final image is hanging in my sons class room right now :)