Keep it real: Honest feedback wanted

Hannah Alvarez2 said:The real deal is all about how you deliver the critique. Personally, I don't have any habit of dressing up the truth, but if the reality is a bit harsh, I'll wrap it up nicely first.

Think about it: saying "this is total garbage, everything is wrong" versus "you've still got some work to do to hit your target" can basically mean the exact same thing. But the reaction? Totally different. One leaves people feeling completely defeated, while the other actually lights a fire under them.
It's like weather. Rain and hail are both just precipitation—it's all just water hitting the ground—but one helps things grow while the other just wrecks everything in its path.

To be perfectly candid*, the first sentence you mentioned is far more palatable to me. The second sounds like condescending patronization; after all, how could anyone possibly presume to know what level I am personally aiming to achieve? Phrasings like that, much like the construction marked with an asterisk (*), almost cause my Lie Detector to redline every time I hear them. I prefer concise, concrete answers over this sort of New Age managerial nonsense.

On a final note, I suspect you may need to spend some more time studying basic grammar if you hope to reach a level where my stomach doesn't turn at seeing "hailstorm" and "encourages" used in such a manner.

I suppose it all depends on the specific circumstances at hand.
It isn't quite the same thing whether one is offering feedback to colleagues or perhaps even a supervisor at a firm like Goldman Sachs... generally speaking, in those kinds of environments, one has to be incredibly cautious regarding how—and more importantly, in what manner—that criticism is delivered.
Personally, I feel that the matter is entirely different when dealing with intimate relationships, such as when you want to speak candidly to someone very close to you—someone you have weathered many storms with and who knows you deeply, just as you know them (be it a partner, a family member, or a lifelong friend).
In those instances, I don't package my critique the way I might at a university lecture or within a corporate office; while I intend to be honest in both scenarios, the delivery wouldn't be identical. In professional settings, I would still state my opinion, as I find hypocrisy and pretension to be quite distasteful... I cannot change that because it is simply part of my core nature, I don't play roles, but I frame it such that it comes out as, "this is merely my perspective, and you may agree or disagree... but this is what I think, since you asked," or perhaps, "if I were in your shoes, I would act this way, but the final decision rests with you."

However, among those individuals with whom I share a profound closeness, we all know that such relationships aren't solely composed of pleasant moments; if you have truly known one another for a long time, there will inevitably be arguments and various tribulations.
Certain relationships endure both the good and the bad periods, especially if you are in constant contact over many years.
In those cases, I don't tend to sugarcoat things much, perhaps precisely because those same people have, at times, directed rather brutal criticisms toward me, which makes me feel little need to be diplomatic; instead, I just say it straight, simply because that is the nature of our bond.

As for those who struggle to accept criticism—whether it is carefully packaged (which is arguably worse, as one tries to be a diplomat only to have the other person take offense despite having requested an honest opinion) or even when it is blunt—well, that is ultimately their own burden to carry.
Perhaps I am only speaking this way because I was fortunate enough to grow up in an environment where criticism was frequent, often unsolicited, and quite harsh. I have become accustomed to receiving it, and now that I am a grown woman who understands herself, I can discern whether someone is saying something merely to insult me or if they are pointing something out for my own benefit (even if they haven't wrapped it in a pretty bow).