First, be sure to cut the top wide enough for your little one to reach all the way down inside easily. I used a sturdy metal ice cream scooper to scrape all of the pulp and seeds from the sides of the pumpkin first, then it was Monkey's turn to dive in and pull it all out. Loosening everything up first let him focus on the squishy, icky awesomeness that IS pumpkin pulp!
After he'd pulled everything out and we set the seeds aside for roasting, I handed him a Sharpie and had him draw a face. He started with teeny dots for eyes, so I reminded him that I would need a large shape to cut out and he tried again.
Once the face was complete, I did the cutting and he was thrilled to see his drawing come to life. He couldn't wait to see what his Jack-O-Lantern looked like in the dark, so we found a dark room and tested it out.