Generally, you probably won't have to worry about diffraction softness unless you're shooting extreme macro and need ludicrously small apertures, or you're stopping down to shoot deep-focus scenes where both close and distant subjects need to be in focus (landscapes come to mind).
It's often good to know the point where stopping down your lens will start causing you to lose sharpness to diffraction, and using that as a point to work from. For example, I know that for most of the macro lenses I've used, f/11 seems to be the magic number where sharpness and DOF meet.
One thing I have discovered is that diffraction softness is far easier to correct with post sharpening than a subject that is blurred due to missed focus. I find for this reason that there are some occasions when it is better to stop down and ensure that I don't miss the focus. This shouldn't be an issue unless you need to stop down beyond f/11 or f/16; macro photography or landscapes in bright light or with telephoto lenses are the only situations that come to my [mind where this could be an issue.