Every day I struggle with a dilemma. I read countless emails from people we are supposed to respect and from whom we take direction. Usually these notes, presentations, and dissertations are rife with grammar and punctuation errors (not to mention annoying buzzwords).

Should I kindly respond to these people and helpfully point out their errors and risk looking like a know-it-all jackass? Would they appreciate my help, or just be annoyed?

I think I'm better in the long run letting their errors go. While, the huge majority of readers won't know the difference anyway, the handful of others who catch the blunders will certainly think the author is a moron. That makes me happy.