Help me ask why you didn't just

"What are the limitations that prevent us from using sshd?" This has the best chance of being interpreted as Response 2, allowing the person to provide this information.

When someone is not insecure, they won't take offense even if the speaker meant "response 1" and if they are, even "response 2" would cause them pain. In the end, one interprets other people's intentions based on what they actually think (or fear) about themselves.

Because of that, if you are a sensitive person, working around other people's insecurities is a difficult thing. I think that if you are trying to take care not to cause the other party to take offense, then "including a ridiculously long and pleading disclaimer before what should be a short question" is not such a bad idea. You're treading potentially dangerous waters, who said you should be able to go fast?

I often would say something like "I don't mean to be rude but I'm curios, why does sshd not work here?" with a non-confrontational tone and a genuinely-intrigued expression.

> Some people might be offended or sensitive to direct questions, but that's for them to work through with their therapist.

It's a fair position to take, but in some cases where successful communication is a necessity, that stance doesn't cut it.

My go-to heuristic is "the wordier the question, the more likely it is to be perceived as well intentioned."

So if I'm wondering why someone didn't use sshd, I might say, "So I'm wondering if you considered using sshd for this? You probably did, I'm mostly curious about how you think it fits into things."

Wordiness works in my favor in two ways. One, the extra words help me to be precise in my _intent_ behind what I'm saying. Fewer words may, in some cases, technically be more precise, but have a tendency to leave the other person considering whether their initial interpretation is really the correct one or if there is some other implication to the words they're not seeing. Using more words cuts down on that effect quite a bit. It narrows the search space, so to speak.

The second way is that because I'm presumably actually speaking the question, it allows me to closely shape my intonation to be as neutral as possible. I say neutral rather than non-threatening, because non-threatening makes me think of how one speaks to a child, which is definitely not what you want when speaking to a colleague. And of course, you don't want to sound like you're coming from a position of superiority either. I like to think of it as an adventure between me and the listener to solve the puzzle. That takes the focus off some implied power struggle between me and them and instead frames things as the listener and I teamed up to slay the puzzle-dragon.

Number two doesn't apply if you're communicating through text, which is why it's important for those who communicate through text very often to have a tendency of always assuming the best intentions of a given piece of communication until proven otherwise, or by intentionally asking for clarification when necessary.

I was born when my dad was about 41 years old. The significant generational gap between us caused some difficulty in the way we communicated with one another and so I was forced to adapt my approach to communicating with him as I grew up. Now that I'm older, I find that I'm exceptionally good at communicating with other people where cultural differences between the communicators might otherwise result in issues for someone without the same type of "training" as me.

The downside is my written communication tends to be annoyingly wordy. Ironically, my high school English teacher didn't like me very much.

EDIT:

And knowing your audience is important too, of course. The direct, "Did you consider using sshd for this?" would be fine if I were talking to a senior dev, or someone I know is unlikely to take offense to a direct question. Actually, in the particular case of a senior dev, I'd probably reword it to be, "Why didn't you use sshd here? I would've thought it would be useful because of x, y, and z." This frames it as me asking for guidance from the master. I like to bring the wordiness technique in for cases where I know the listener has a tendency to take things the wrong way. Definitely not to be used all the time or else you get a reputation for being a wordy speaker.

Replacing ‘why’ with ‘how come’ turns a seemingly judgmental question into a curious one.

I prefer to ask what they’ve already tried so far, though, instead of jumping to an immediate diagnosis. At least then your ‘how come’ question can point to a novel solution they may not have considered. Because you know what they already have tried.

The problem is the prescriptive nature, i.e., being very tied to force the "sshd" into all of these examples. You need to ask more questions leading up to figuring out if sshd suggestion would even be applicable, and if you get the point where you've done that, and you haven't heard sshd mentioned yet as something explored, then that's the time to bring it up.

And I'll add, it's not condescension that's the big issue here, it's that suggesting technologies before you fully understand a problem suggests a specific level of naiveté that people are on the lookout for. I can exactly place a person's technical problem-solving maturity level by how quickly they get to throwing out technical solutions, because people that have been around the block may have these ideas in their head, but they also know the questions to ask to ferret out where the complication lies.