I've been in this situation in the past and it might not have been the last time (working in the tech industry, I've seen this type of behaviour also from other peoples' superiors). So I'm wondering whether there's anything useful, helpful, and/or kind to do when confronted with (such) a socially challenged superior - other than or in addition to following SO Workplace Rule #1: Get a new job!
Let me explain: I've had this boss (CEO) who had trouble picking up on cues on his employees' emotions (in particular "negative" emotions) and requests for support. A partner company failed to deliver an important dependency for the third time in a row and a colleague was angry about it and asked for support? "Well, nothing much we can do about it..."
As far as I can tell, this was never malicious - he just didn't notice or grasp the relevance of the problem. Or if he noticed, it was with a delay of months, when the anger at being ignored had already built up, leading to fights with completely frustrated employees and - in at least one case I know of for certain, possibly more - to an exceptionally productive, valuable, kind, and helpful employee quitting in anger. At which point the boss was surprised by the anger and distrust he received and didn't know how to handle the situation.
This boss had a... let's say: very focussed working style - focussing on one problem/project at a time (for months) and disregarding most other issues/projects, which, accordingly, started piling up. When notified of these issues, he'd discard them as unimportant until he couldn't any longer, which, again lead to frustration for his employees, who were then called in to put out the fires.
Also, he had a taste for the path of least resistance, meaning that in frequently the person kicking up the biggest fuss would get their way.
Now, in my eyes that's not a way for a boss to behave. But attempts at discussing some of these issues were - again - mostly discarded or talked down. (Besides, there are so many ways a discussion about "Your management style needs improvement NOW!" can go wrong...) Sometimes there was a short-time improvement but since it took him a conscious effort to uphold, everything reverted back to (un)normal when he was under stress again. (And he was good at creating stress for himself.)
I had a strong feeling that this whole mess stemmed from some sort of mental issue or other. But I'm not a psychiatrist and going around armchair-diagnosing your boss doesn't bode well for your career and isn't respectful.
However, since he was a well-meaning, friendly, helpful, even charitabl eperson (when not completely oblivious to others' feelings - I know this sounds weird as hell), I wonder if there was something productive and/or kind I could have said/done for him to improve the situation. Because not only was it difficult for the employees, it was also unpleasant and stressful for him, and it cost him in talent and motivation.
I'd like to hear in particular if you've been this boss in the past and found a productive way to deal with it. Was there a book or other resource that helped you? A metaphor that you understood and lead you to change something? An event that took place? Something that may have been a small nudge in the right direction to lead you to a happier path?
Or did the happier path come about simply because the naysayers quit and you could finally work without being interrupted by all these useless discussions?