I am very bad at reading if people are being snarky, difficult, etc and usually take people at face value — should I be taking more offense? When do you know when to push back or say “oh this is not clearly not a well-intentioned person”?

I've worked a lot of roles, whether it was on the ground, technical, leadership, "customer relations", etc. The main uniting factor was coordination. I would like to think I'm pretty good at this, but there's something that comes up a lot —

Let's say I'm trying to set up a meeting, and I state a proposed agenda, etc. Another party comes back to us asking what I take to be clarifying questions. I take this to my peers and supervisors, and they immediately say "that guy is a jerk" (some history there, granted) and read the reply as snarky and "being difficult".

In a vacuum, if someone makes stipulations or asks for additional things, I just find ways to achieve it and don't read into it. I take people at face value a lot and feel like it should be more obvious if someone has some nastier motive or is actually being purposefully obtuse — by doing the (what I regard as) reasonable asks, I feel like the intent to be difficult will become more transparent if that's the case. Again, I don't think too much about it until it's obvious.

But this goes towards social situations, too. Generally I lean towards "I'll take accountability for myself" and don't read into people too much. I feel like this helps me be diplomatic or even likable, but I also wonder if my inability to read poor treatment allows me to get walked over or prevents me from pushing back when pushback is needed. Social skills are needed everywhere, whether personally or professionally, and so it got me thinking about this more broadly.