: I'm afraid of quashing the hopes of a new writer I recently agreed to read a new writer's novel and provide feedback. During casual discussion, I learned her mindset is currently in a state

I assume you've done a great review. This seems to me a matter not of how you've done your review or what your feedback is, but of how you present it. Here are some great strategies you can use when presenting the feedback to her to encourage her and increase her receptiveness:

Start with positives! Try really hard to find things that she has done well. Focus on areas where her writing was good, however small they may be. Once you start with positives, it helps to increase her mood and confidence and also sets her up to be more receptive. It's easy to think of someone as an overly negative person if all you receive from them is criticism, which is likely to result in dismissal, so always start with positives!
Focus on your own mistakes! As you mentioned, you had a lot of past experience and made a ton of mistakes yourself. I would not be shy at all to share with her your own mistakes and especially if you made the same mistake. You can share some great stories and also avoid the appearance that you consider yourself better than her or that you don't make mistakes yourself.
Make things easier! It may be overwhelming for her to receive and review all of the feedback at once, depending on how thoroughly you have done your review. There can quite simply be a lot to take in, so it could be overwhelming! Try to focus on simplifying your feedback into maybe three key points. You can group things together or consider presenting some items at a later date.

I would definitely try to present your feedback in person as that would show you care more.

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As a frequent beta-reader, often for friends, I struggled with this question -- and I'm pretty happy with the answers I've figured out.

Don't pronounce judgment; help the author level up

It makes a lot of sense to tell an author, "Listen, I don't think this is ready for publication." Because, really, isn't that the most important thing?

Well, it is, kind of. But the problem is, it's not very helpful. As a beta-reader, your goal isn't for an author to publish or to give up blindly, on your say-so -- it's to help the author understand better themselves. You've done a good job if the author understands your issues with their book -- not just a thumbs-up/thumbs-down final grade.

And here's the magic of that: If you've done a good job explaining what the issues are, you don't need to say "this isn't ready yet." The author will understand that on their own. They'll see problems that didn't register before; they'll want to fix them.

That can still feel overwhelming and harsh, to be sure. Which is why I find that:

Detail is better than sweeping statements

A comment like "I didn't connect to the protagonist" could point to a serious problem with a book. But as a criticism, it's kind of broad. Particularly with an inexperienced writer, they might simply not understand what that means, where it's coming from, or how to fix it.

What I've found is that the biggest problems in stories are often hard to pin down -- they're not any one thing or a particular section; they're the accumulation of tiny issues into something much larger. "I can't connect to this character" might be the accumulation of moments like "Wait, doesn't he have a day job?"; "This bit seems really inconsistent with how he was behaving ten minutes ago"; "How come he never mentions having a family or friends?". Each is minor on its own; but together, you can see where the sense of "not connecting" is coming from.

So: Try and explain, to whatever extent possible, where each point of criticism is coming from. Key your criticism to the text. This makes your points easier to understand and digest; and it also makes them more fixable. This might feel like dumping more criticism on the poor author -- but if you do it well, you're breaking big harsh writing issues into smaller, bite-sized morsels, that the author can grasp and consider and fix.

I've written in the past about how I do my own beta reads. This might not help you this particular time, but I feel like this has been such a help to me: My beta reads always include notes I jot down as I read. Notes just capturing my immediate reactions. Not "fix this," just "I'm feeling this right here." Why is this helpful? Because it documents my own feelings and reactions, in a very detailed way. And feelings are pretty persuasive -- you can argue with analysis, but you can't argue with the fact that I felt X when I read Y. And this gives me two things: (1) the author gets insight into my reading experience, and (2) I can refer back to my reactions at a specific point when, at the end, I do want to make some larger point. This takes a fair amount of work, but it's very effective and I highly recommend it.

Be diplomatic.

It's very easy to come across as dismissive or condescending, when you're giving detailed criticism of somebody's work. That's a bit beyond the scope of this question, but I highly recommend the Critters Diplomacy page for great, concrete details of how to communicate criticism diplomatically.

Identify the story's strengths -- and its goals

A piece of advice you'll often hear is, pair negative criticism with stuff you did like about the story. This really is crucially important -- as a critical reader, the bad stuff can really stick out at us, but pointing out what the story does do well is just as important.

(And, it's definitely worth acknowledging the accomplishment of writing an entire book or short story, even just a first draft. That really is huge.)

What's no less important is identifying the story's goals. Is it trying to be a zany romp? An affecting romance? A pulse-pounding thriller? Even if you feel it's done so poorly -- maybe especially if it's done so poorly -- point out the goals you've identified. Tell the author, "I see what you're going for here."

Because:

That places you firmly on the author's side. The author may not have done a great job accomplishing their goal, but by goodness, you understand what they're trying to do, and your advice is there to help them accomplish that.
This gives you a lot of positive things to say even when the story is very weak. Even if nothing in the story is working for you, the author's intentions are good and you can appreciate them. This lets you strike a much more positive tone -- not "this is really bad", but rather "this is aiming at something really good but it isn't there yet."
Lastly, sometimes a beta-reader can be way off-base with their reading and viewpoint. Maybe they don't click with the author's style; maybe they're beta-reading in a subgenre they really don't get along with, or are unfamiliar with. If you've mis-interpreted the story's goals, the author will understand that you're reading from an entirely different viewpoint. They'll have a much easier time understanding your comments as coming from a reader who was looking for something else -- and that's a really good thing to know.

When you max out -- stop

Sometimes you read something and despair of it long before the finish line. Maybe it does something that turns your stomach and you can't read any more of it charitably; maybe it does one annoying thing again and again, and all your comments are going "STOP DOING THE THING ALREADY".

Then: stop.

You're allowed.

You are not obligated to beat the story into the dirt, or to chronicle every fault and misdeed it contains. Your goal is to help the author improve, not to tell them how bad they are. By commenting up to page (X), you're giving them helpful, valuable feedback -- the work they need to do to fix it, if your comments are good ones, is already plenty.

And the simple fact is: if you reach the point where you're hate-reading a story -- where you're getting nothing out of it except enumerating its faults -- then you're not in a great frame of mind for giving helpful, constructive criticism. Your points may all be good -- they may be great! But if the underlying story is "I am sick of this story 30% of the way through," then offering tucks and polishes for the last two-thirds might cost a lot more than it's worth. For you, as a frustrated reader; and for the author, who gets a bunch of grumpy notes piled on top of the more fundamental criticisms. Better to kindly and constructively say "I stopped here; here's what I think you can improve", than to wring every last problem out of a story you can't stand.

(I'm not saying "abandon a book that's sub-par"; there are plenty of books that aren't ready, but can still benefit lots from a full beta! The difference between "this book is not ready" and "I hate reading this book; it makes me angry" is important.

Also, some structural issues are really hard to address without knowing where they're headed at the end -- those might require special care, or just flipping ahead to the end.)

The bottom line is: Writing is hard. Much harder than people often realize at the outset. And, yes, that first thorough criticism can be a disheartening experience.

You can't really shield the author from that (and you wouldn't be doing them any favors by trying). But what you can do is approach this as a supporter and a guide; trying to help them see the scope of the task -- and what paths exist to do it well. Be on their side; encourage them to overcome the difficulties even as you are unflinching in pointing out what those difficulties are.

Best of luck to you. You sound like you're making a great effort to help out writers both helpfully, and compassionately. Kudos, and all the best.

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First, let me say how wonderful it is to have a question from a reader, about helping a writer, for a change; we need more of these.

I apologise in advance if any of my "do X" advice is something you've already thought of; I don't mean to patronise. I also apologise in advance if you think any of this advice is bad, in which case you can ignore it. (You have to love the irony.) Having said that:

No matter how much work it needs to be publishable, I guarantee there will be much that is good in her manuscript. Mention what you can, not just to soften the blow, but to help steer her; you wouldn't want her taking out the good parts! I'm not saying literally every way she could have messed up but didn't should be praised, but at least tell her what you liked, or (if you're struggling for that) what other readers are liable to like. You can also focus on what was done best, even if only in the sense of least bad (but you don't have to say that!) For example, if some of the characters aren't fleshed out enough, I'm sure one or more are especially well-crafted compared to the rest, so at least say that.
In what order will you make the points? The obvious option is by importance or chronology, but give it a little more thought than that. Assuming your concerns include a lot of little things, I suggest dividing the feedback into sections by issue type, and then in each section you can replace the importance criterion for sorting with "how important is it to fix, relative to how easy it will be". You'd be amazed how many of a beta reader's points can be fixed with edits to, or addition of, a single paragraph or less. And yes, there will be things that require much more of an overhaul than that, but get to them later. That way, by the time she notices such feedback exist, she'll have thought, "I can fix these ones quickly". (If you can, in fact, identify which issues need only a little work, I'll mention in a moment a "colour coding" approach that might persuade you to appropriately colour this kind of feedback.)
You can't make her agree with you on anything, or be happy to read something she disagrees with. What you can do, however, is say what it takes to make her come to certain conclusions on her own. For instance, "I'd fix X", no matter how "but to each their own" the presentation, could go down badly if too frequent. Yes, you'll need to say it sometimes. But where possible, say what you thought/felt when particular things happened, and make clear with such things you don't know what she intended, and she can use it as a guide to whether her intent worked. You might even open with a colour-coded key so you can send different kinds of message in different colours. Then, when she sees blue, she'll think, "I wonder if it had the effect I meant it to". Some feedback should be phrased as "this is how it comes across" rather than "it's a shame this went the way it did". Obviously, when you think the protagonist is a bit of a numpty early on, only to improve as a person later, in a way that's supposed to happen.
This is a point I'm mentioning late, but it probably needs to affect your write-up early. Relate some of her fumbles to the changes you've had to make before. Whatever mistakes she's making, I bet most of them are the kind people usually make; it's just statistics. The takeaway needs to be "This is what new writers need to work on", not "This is what only you need to work on". Again, it's about how to make the horse drink. Ideally, she'll realise she needs to read more, even if all she reads is writing guides that summarise what other people learned by reading a lot of fiction. After all, if you tell her lots of writers tell when they should show, that they should show isn't a lesson you learned from any novel; it's a lesson you learned either from many novels in which you saw as a pattern that showing helps, or from a much more succinct discussion of it in a writing guide. If any such guide has helped you, mention it!

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