Research affirms that trying to improve all that may be troublesome in a writing sample (at the same time) may do more harm than good. Pace your feedback to the writer's psychological state of mind. For the writing to improve, you must consider the context in which it is being written. Also, what is that person's present state of mind? Attitude toward writing? Attitude toward what is being written? ...Oh, that everyone who offered fiction feedback would first read this advice. Between writing classes and online workshops, I've interacted with more than a few people who believe that the thoroughness of a critique determines its quality. No missed punctuation goes unnoticed, no cliché unskewered, no questionable motivation ignored, because that's how we get better, right? You can guess how this goes with non-professional writers, those whose manuscripts possess such errors in abundance: They become discouraged and, if regularly exposed to such counsel, eventually put their pens down for good.
Before sending their writing out, wise writers recognize the importance of "trying it out" on a real audience -- like having a dress rehearsal. When someone asks you to see that rehearsal, remember: The idea is to "break a leg," not a psyche!
Proponents of what I'll call the thoroughness view forget that one improves not only by noticing his faults, but by continuing to write after doing so. Sure, someone's short might be pure tripe, as three-dimensional and weighty as a sheet of letterhead. If it is, you won't be the one to fix it. The author might not be the one to fix it. It might be unfixable. Yet if the author keeps writing, perhaps he'll overcome his favorite flaws over time, one by one and step by step. So offer advice on a handful of the biggest issues, and let it go at that. This is precisely what Neil Gaiman proposes for those offering writerly criticism:
It depends on whether your friend wants to be a real author one day and learn his craft, or whether he's just proud of having made something. When it's the latter, I just try and find something positive I can say that I mean. If it's the former, I try and tell people how they can make something they've done into something publishable, or fix it, which is going to involve pointing out it's not publishable yet. ...(Picture: CC 2010 by foshydog)
And if you do decide to tell them what's wrong with their book then you don't have to tell them everything that's wrong with it. Pick the biggest thing -- "I hated all your characters and kept hoping that they would die and that we would get nothing but a description of the landscape for the rest of the book" or "It reads like you're recounting a D&D game, not a novel" or "All of your characters sound like you" or "Nothing actually happens until Chapter Four by which point anyone who isn't a personal friend of yours would have stopped reading" -- and talk about that. Don't do a laundry list...