Help me ask why you didn't just

> "I'm probably missing something - why didn't you just do X?"

I like to use basically this, combined with brlewis's suggestion to take them out of the phrasing, when I'm erring on the side of being approachable. So maybe "I think I'm missing something here - why not use sshd?". If it's awkward to take them entirely out of the equation, there's the royal company "we" - e.g. "why don't we use sshd?"

Some of Mark's rephrasings are rather over the top. "I'm not clever enough [...]" whoa there, that's a bit much. You're either being sarcastic, or beating yourself up way too much. "There must be a good reason why you [...]" whoa whoa, they might not, and that's fine! There might be a good reason... there might be a bad reason... there might be no reason... and all of those are fine! I ain't judging! I've probably had worse reasons! I just want to understand the problem space.

"I think I'm missing something here" admits to an extremely minor, low stakes, inconsequential "mistake" on my part - the kind that we all make frequently enough in passing as to not even really think of them as mistakes per se. I'm not admitting to some moral failure, just implicitly asking for a minor bit of assistance from my conversational partner to get over a momentary blind spot. It's not judging either of us, the problem, or the solution.

Which all hopefully helps set the tone - for if they feel like they've made a mistake because they didn't think of sshd and realize in retrospect that "they probably should've". Because, like all of us, sometimes they have overlooked the obvious... but that's perfectly OK - because, like I said, it happens to all of us.

> And honestly I think phrasing isn't that important - if you know someone for months or years and aren't usually a dick - people won't automatically assume the worst.

Also agreed.

Hmm, using "you/your" and asking them to explain their actions actually comes off as accusatory to me.

Compare that to "Why doesn't sshd work here?" (mentioned elsewhere in the comments), which seems more focused on education.

"What benefits does your project offer over sshd?"

I use this because 90% chance the person has an answer ready for the exact question. "sshd is more difficult to deploy in blah blah situation", which is an emotionless answer.

I disagree; "Why didn't you just use sshd?" is a valid question and can be answered as such. Of course the answer might be "I don't know", but also there might be an answer, and maybe they do know the answer and have a good reason to don't use sshd; I don't know. That is why I ask. Then you can learn.

Someone may be genuinely interested in feedback. In such cases, you want to be polite and respectful while still communicating that "This is my first thought." It gives both parties room to maneuver and save face. That framing makes it possible for them to reject the feedback without suggesting anything negative about you (like "No, you're the idiot here!").

You may be genuinely trying to understand it yourself, in which case it's going to be easier to comprehend what's going on if you can relate it to the existing framing in your mind without offending them. It takes a lot of time and energy to mentally move from "My first thought is X" to "How do I say this in a way that elicits information without me sounding like I'm judging...etc?" There isn't enough time and energy in the day for every single social interaction to meet the standards for some kind of international diplomatic mission, but you also don't want to just excuse outright rude behavior. It's reasonable to explore your options if you as an individual run into a particular social thing repeatedly so you can handle it not horribly without being at the top of your diplomatic game every nanosecond of the freaking day.

Last, if you have enough education/experience related to X, you may actually have a better answer at first glance. They might actually be interested in improving it and open to your suggestions -- again, if you can share that information without unduly stepping on toes.

Sometimes trying too hard to be polite and respectful and perfect is actually antithetical to any kind of meaningful communication. Good social practices have to be tolerant of a little friction while seeking to lubricate it so it doesn't rub people the wrong way to an aggravating and problematic degree.

This is counter-intuitive. To genuinely connect socially/intellectually, there will be some friction. If there isn't any friction, you aren't actually connecting with people. But you don't want it to be excessively rough because that's counterproductive.