My career as an architect had reached a point where I knew it wasn't going to satisfy my life goals. I needed to understand more about finance, innovation theory, management, etc. I needed an MBA -- not a bullshit one for the title, but to actually learn things. I decided I'd go to Oxford.

This was going to be challenging: I had neither the funds to pay for it nor the shiniest academic record. Good GMAT scores, but not much else. The admissions essay had to be a knock-out.

So I wrote something I thought was amazing, and was preparing to submit it, when I realised: wait a second, I need some more eyeballs on this.

I looked around the coffeehouse where I sat. There was a guy there -- I wasn't sure of his name, but he was a regular. A philosophy student (part time? dropout?) of uncertain provenance. We'd had a few conversations occasionally, and he seemed bright. So I asked him, somewhat rhetorically, whether he had the time to read 4 pages and give me his feedback. He happily agreed...

...and he hated it. Tore into almost every part of it. Didn't remotely grok the point I was trying to make. Made it clear that the essay failed on pretty much every level.

That was unpleasant to hear, but he was right. What mattered wasn't _my_ impression of what I'd done -- it was how it impressed other people. So I rewrote the essay from the ground up, keeping his criticism at the forefront of my mind.

Oxford ended up giving me the largest scholarship they had. Afterwards I stayed in the UK and built a life there.

Don't even know that guy's name, but damn am I glad he was that asshole.

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.

It seems like the fact that he didn't encounter this sort of thing until his sixth book ended up making this a lot more stressful than it needed to be, and a lot more work for both him and his editor.

Because he had such a strong relationship with the editor, he likely did not have to write a detailed book proposal, in which some of the structural issues might have come up. The editor seems to have heard a general pitch -- "dual biography of Churchill and Orwell, with a focus on how they each, in their own way, fought against totalitarianism" -- and agreed to get on board on the strength and quality of their previous collaborations.

And then Ricks had the liberty of working on the book for _three years_ before dumping the completed manuscript on the editor.

Both the writer and the editor share some blame for the fallout from that. As Ricks says, this was not a rushed job. You would think that over the course of those three years, there would have been communication between writer and editor on how the book was shaping up.

With journalism and nonfiction writing in general, you sometimes don't have the ability to predict at the start how things will come together structurally until you've done all your research and reporting. Sometimes you have to change directions. But it seems like those profound structural issues could nevertheless have been caught at an earlier point in the process.

If you want to learn about Orwell, read Orwell. He does write about himself occasionally, and rather critically.