When I'm quilting around an item (my pumpkin and leaf), always work in a clock-wise manner. This way the pumpkin and leaf get puffed up and they look like they have been stuffed (but they are not).
Once the outside of the pumpkin has been hand quilted, then move onto the right hand side of the pumpkin and start hand quilting (see black arrows) beside the embroidered lines going from the top to bottom. Start at the far right and move towards the centre. My quilting will be on the right side of the embroidery lines. Then, quilt the next two embroidered lines (see green arrows) with the quilting being on the left side of the embroidered lines.
Follow the same procedure for the leaf (blue arrows). This photo shows my quilting beside the embroidered lines. Can you see how the centre portion is nice and puffy? Remember, clock-wise will make my pumpkin and leaf puffy.
For the grid work, there is also a pattern for quilting those also (see black arrows). My quilts gets marked up using Crayola Washable markers (the fine tip markers). If you want to read more about these markers and how to work with them, just go here and scroll through the posts.
All of my pumpkins, leaves and grid lines will be done in this manner. This way, there is nothing that gets distorted and looks odd after all the hand quilting has been done.
Hopefully, this post will help clear up some of your questions.
Have a great day!