Speaking of tone, the phrase "I need you to X" is super condescending. You're not his superior, and he's not your child nor your subordinate. He is not behold

Speaking of tone, the phrase "I need you to X" is super condescending. You're not his superior, and he's not your child nor your subordinate. He is not beholden in any way to what you "need." Much better would be to just use good ol' "please": > I know it's a hard ask on this site, but please start parsing content and not tone