Darts are part of what makes great fitting adult clothes but sometimes it isn't obvious where/how to put them in. This
http://www.ikatbag.com/2010/09/drafting-part-xi-princess-seams-and.html is a resource I find myself going back to regularly.
For something flat and square like shams, bring the pillow (or, even better, an existing sham that fits the pillow) and tell the person at the cutting table what you are trying to do. For flat things like that you can actually lay it down on the fabric to see whats needed.