The best time to prune pittosporum hedges as well as other trees and shrubs is in the late winter or early spring, before the plants have broken dormancy. Once plants are in an active growth phase, pruning opens them up to infection. They are more resistant while dormant in winter, so if you are doing yearly maintenance or major trimming, save it until then. Only prune at the end of winter, however. Clipping hedges in late fall or early winter can sometimes encourage growth; if that happens and a freeze occurs, plants can suffer or die.
Pittosporum tolerates shearing well, so you can trim it every year if you like, as long as you begin shearing when the plant is young. When trimming a hedge, make sure you still have good penetration of light and airflow to reduce disease. Clean equipment before and after use by applying rubbing alcohol to blade surfaces. When you prune a pittosporum to form a tree, you want to encourage its natural branching structure along with an open canopy.
Pittosporum grows quickly, so you might find that you need to trim it more than once a year to keep it looking its best. Many people trim it again after it finishes blooming, as pruning beforehand runs the risk of chopping off all the fragrant blooms. If your pittosporum contracts a disease, remove damaged wood 6 inches below the infection site. When pruning diseased wood, be especially careful to decontaminate blades between every cut.
If you can, minimize pruning. This reduces the chance that plants will contract infection through open wounds or contaminated equipment. The best way to reduce pruning is to choose species that match your landscape needs. While many types of pittosporum grow 8 to 10 feet tall, several grow to only 2 or 3 feet. Depending on what you are using your hedge for, you may do best with a much smaller specimen. Whatever size you choose, ensure your landscape can support it. A foundation site under low eaves, for instance, might not be the best place for a tall pittosporum.