I also heartily recommend that book: it is fantastic.

But in regards to “negative comments” one challenge is what to do when faced with a situation where you sincerely believe something is harmful if not strongly countered?

For example yesterday on HN there was a post about online dating, and a number of comments espoused an idea I viscerally believe is actively harmful: that you should strive for some idea of “good communication skills” that facilitate reading strangers’ body language in public and determining how to make an advance for dating.

Now, I really believe this is harmful advice: it leads to actually hurting people in the form of perpetuating social norms that bother people in public and put them in unwanted, uncomfortable positions, and cause impressionable readers to believe this is not just OK, but even healthy.

In a case like this, I am still at a loss of how to apply the sincere listening and positivity approaches of How To Win Friends... because there’s an overriding moral implication that the statements have to be visibly refuted and challenged, not to “win an argument” not to persuade the original author, but to leave a visible marker for impressionable readers about the serious danger embedded in what’s written, to spell it out clearly and not leave it to chance interpretations.

> that you should strive

I think that terms like "should" or "ought" are toxic. I can try to express ideas in an objective way with limited assumption, starting with how I present the ideas. Typically, I have found the substitution of "I think" puts my thoughts in perspective. This has led to a few times where arguments felt genuinely fruitful.

That is an extreme view. It means all types of advocacy are toxic.

That is demonstrably incorrect. My first post advocates for benefits that might be found in a discussion without using specific verbiage.

That seems like a semantic distinction only. Extolling the benefits of something is not advocacy, at least not how I understand the term advocacy. Advocacy means representing a normative view of what ought to be the case, and suggesting that others should take certain actions. It necessarily requires an aspect of asserting a moral stance about the rightness or wrongness of adopting or failing to adopt certain actions.

> That seems like a semantic distinction only.

The semantics matter because of subjective interpretation. "I think" and "should" and "the majority of subgroup x" are not usually correlated to be the same thing, even though they seem like "semantics". The first is clear (why do you think that?, is rarely asked), the second undefined (should doesn't have a qualification) and the third subject to investigation (based on what evidence?).

I have found that morality is less often an influential factor (spaces vs tabs, fight) than the words like "should" and "ought" are used. YMMV