It's so difficult to give frank, negative feedback without coming across as an asshole but, sometimes, it's necessary.
"Constructive" feedback only goes so far. Sometimes people need to be told that their work is bad, so that they can improve. Accepting mediocrity in order to avoid hurting someone's feelings is doing them a disservice in the long run.
Scott is unlikely to be an asshole. His, was a friendly comment. From what the author wrote, the comments allowed him to ponder and make the manuscript better. So constructive criticism does work.
Of course, delivering bad news is hard. Most people are awful at it. Most people don't really want it. They want a pat on the head and get told their work is near-perfect.
I advise on a few startups and mentor at Techstars Austin. When a company asks me to watch their pitch, I ask them: "Do you want honest feedback no matter what or just a thumbs up? I'm happy to do the first but I won't do the second."
The relationships that come through honest, constructive collaboration are the best part of mentoring.
So it may help to have an inner asshole when doing this.
I have met some people who take this as a license to not think as hard about how to formulate their feedback. So it comes out as harsh and personal, even if the kernel of feedback is valuable.
Almost every "angry" feedback I've seen on the internet could have been rewritten to simply be good feedback. If you have the time to write and rewrite feedback, you can probably clean up arguments much faster. Taking a chill pill if you will.
This is harder to do in face-to-face conversations, though.
There seems to be a need to for continual escalation of feedback until it is processed. Often times this processing doesn't occur until they are uncomfortable, or as in the case of family, tired of listening to you!
Then phrase it another way until they do, or otherwise find a way to communicate it that makes the issue clear. That's still not a reason to become hostile or toxic, or berate or denigrate someone.
And bringing things back to the article we're commenting on, here: it doesn't actually look like that happened at any point here. Despite how the person in question self-described themselves, it doesn't seem to me that they actually behaved in a problematic way. It's perfectly reasonable to offer precise, to-the-point, clear criticism. None of that requires being rude, uncivil, or unconstructive.
The comment I was replying to said '"Constructive" feedback only goes so far.'. I emphatically disagree; the article talks about a ten-page letter full of what sounds like highly constructive feedback.