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The best time to prune Japanese flowering cherry trees depends on where you live and the type of flowering cherry tree. Some trees benefit from being pruned toward the end of winter or early spring, after the last freeze. Meanwhile, other trees do well after blooming, in late spring or early summer. Avoid pruning your flowering cherry tree in the early winter, as this encourages open wounds that can lead to infections or infestations. 

You should prune ornamental trees once every other year after the fruit has matured and begun to drop. You should also prune out dead branches whenever you see them. Pruning too often can stimulate more growth, especially in faster growing varieties like Bradford pears.

Generally, avoid trimming trees in the summer (with the exception of pruning fruit trees as needed). Trees use a lot of energy in the summer, most of which is relegated to new growth. If you chop it too early, you could stunt the next season's growth. Again, when in doubt, do some research based on the specific tree type.

Generally speaking, you’ll want to avoid flush cuts, which are cuts made as extremely close to the trunk or main branch. These cuts can weaken your tree, lower its natural defense mechanisms, and even cause decay. You’ll also want to avoid tree topping, which is the total removal of the leader and upper main branches of a tree. 

Most pros will advise against either of these methods, which is why hiring a pro is often the best choice when it comes to tree trimming.