One idea
Telling a coworker, a friend, or a partner that something isn't working is uncomfortable, so most of us save it up until it comes out sharper than we meant.
Most of the sting is in one word, "you." Say "you missed this" and the other person stops listening and starts defending themselves, like anyone would.
So when an idea or an outfit isn't working, I aim at it instead of the person and say five words: "I think we can do better." Nobody feels blamed, so you fix it together.
Then say what better looks like ("What if we sent it Friday instead?"), because "do better" with no direction just sounds like disapproval.
One style tip
Being on time is the cheapest way to look put together.
One quote
"If you have something real to say, being mean just gets in the way."
Paul Graham, in his essay "How to Disagree."
One thing worth reading
Kim Scott's Radical Candor means caring personally and challenging directly at the same time, and this page on her site explains how to do both.
One thing you can use before the weekend
Think of the one conversation you've been putting off. Tonight, write down the sentence you'll open with, and take the word "you" out of it. A sentence you've already written is the one that comes out when you're nervous.
Hit reply and tell me how it goes, I read every one.
Grant
P.S. Big presentation or interview coming up? My Studio does personal styling, media coaching, and creative direction, and the first step is a free 30-minute call: galxndr.com/book