There are a lot of obvious questions to ask about a situation that aren't being mentioned. What is my actual power to influence this decision? What would the most effective line of communication look like? What are the motivations behind this? What do different people think is at stake? What kind of appeal will have the most influence on the person in front of me?

I don't think autism prevents a person from appreciating the importance of these questions. It might affect your ability to answer them quickly or correctly, but it doesn't render you incapable of posing them and acknowledging them as important influences on the situation. A person who is blind from birth can understand that their clothes have color and that color-coordination affects how other people perceive them.

So why do those questions get left out? I think the answer is that some autistic people, including me when I was younger, cling to a very strict idea of what it means to communicate in good faith. I used to assume that if people were speaking in good faith, they would appreciate me taking their arguments at face value and directly addressing the objectives we had in common. They would be rigorous about admitting their motivations and, in general, be willing to be explicit about every factor they were taking into account. I also felt that if they weren't speaking in good faith, I was pretty much screwed and helpless. I didn't have an answer for that. So I handled every situation by striving to speak in good faith, owning my deficiencies in that regard, and hiding any suspicion that the other person wasn't speaking in good faith because 1) I didn't have a game plan for it, and 2) being aware of it made me feel guilty and scared.

Over time it dawned on me that this "good faith"/"bad faith" dichotomy, whatever its merits might be in a society that embraced it, wasn't useful in this reality, because most people don't think in those terms. There are a lot of people of basically good will, who aren't overly selfish, who go through life being mostly nice to people, who also violate the rules of good faith argumentation (as I understood them) virtually every time they open their mouths, and are completely un-self-conscious about it. I had to learn that even though they were good nice people, it was okay for me to be aware of "impure" aspects of communication with them. I didn't have to feel dirty about seeing into the mix of motivations of the person I was talking to, even if I liked them and thought they were a good person.

That didn't make me immediately better at dealing with people, but it was one of those "oh now I can start learning" turning points.

It also led to a big improvement in my personal life. Understanding something about somebody and making use of it without explicitly acknowledging it used to feel dirty to me, but other people want and need you to do it, especially when you're first getting to know them. You need to be able to understand and accommodate people's quirks long before you become close enough to talk about them.

That rule turns out to be just as true in business. When it comes to dealing with people's flaws, what's best for the business is usually what's best for them. It's very bad for someone if their flaws cause problems for the company. They need their coworkers to be aware of their weaknesses and adjust for them, but they probably don't like hearing them mentioned unless you have a very close personal rapport with them (and maybe not even then.)

Anyway, before I accepted all that, I used to obsess about improving my adherence to the rules of good faith argumentation, assuming that anything outside that scope would be scary if not morally wrong. Really, most of the mistakes I was making were caused by me intentionally ignoring everything I knew about the social context of a discussion because I thought it would be insulting to other people if I did anything that reflected an awareness that they might be influenced by factors that they weren't explicitly acknowledging.

How exactly autism or other factors might have got me into that mental cul-de-sac in the first place isn't clear to me. I might have some deficiency in my ability to instinctively read other people's minds and emotions, but in this case, the problem was not lack of insight but a deeply engrained taboo against using the insight that I had. One explanation is that when I was little I wasn't good at observing the taboos around what motivations can and can't be acknowledged, and to protect myself against repeated failures to observe those taboos, I created a blanket taboo against acknowledging people's internal lives. Or maybe my parents instilled some weird stuff in me and I was too autistic to learn different rules for home and school. Who knows.