We have each of the kids draw a few options on paper before they get going on the actual pumpkin. Once they have the design they like best, they draw them on the pumpkin using a black Sharpie marker (or as the kids call them "Mommy markers").
Adam and I are made to cut the top off the pumpkin and scoop out the "guts". Honestly for scooping we have found that a metal soup spoon works the best. All the innards go into a big bowl where we can later roast the seeds. (We like leaving a little of the flesh on the seeds while roasting, they turn out the best that way!)
We then give the kids the Pampered Chef kid safe knives to carve out the face shapes. These are the best for the job! We don't have to worry about the kids accidentally cutting themselves and they saw through the pumpkin with ease.