First, have FUN picking out your pumpkins. If we have time, we spend time at the pumpkin patch and enjoy the whole process of picking out that "perfect pumpkin".
Once home, and ready to start, make sure have some markers, sharpies work well since they are permanent markers. Draw a face without too many details or thin parts, so that you won't actually cut through and break apart the face on your jack o lantern.
Make sure you have sharp enough knives or tools, so that you can do it as safely as possible. If your children are very young, have them help make the face, then you can do the rest, after they have helped to clean the pumpkin out and save the seeds if you want to use a recipe for those.
Keep it light, have fun!! Take pictures, play music, etc. Enjoy the time together creating new memories.