I'll use the conference room example for clarity, even though a lot of people still work remote these days.
Reading the room could be as subtle yet significant as reacting to the speaker that was on immediately before you. It could be reacting to the temperature of the room or the catered lunch everyone just had. It can be noticing or participating in a particular trend of the audience (hawaiian shirt fridays, etc.). It can also be a million other things and they'll never let you get away with choosing at random. You have to just "get it" or you're going to be ignored at best.
You're at once trying to both signal in-group status while also asserting your own identity and setting the tone for everything you'll be saying after. Remote work has its own idiosyncrasies, but regardless, you need a pulse for this kind of work.
Trying to pin that down is simply not logical and it's not just a matter of "adding" a handful of tricks unless you want to alienate everyone. Sometimes it's also the things you don't say or do that make the difference. You also have to accept that you can't please everyone. You could actually piss off everyone but the most important person in the room and still win. The real world is messy and adding AI to the mix just makes it worse.
But things get better if you instruct AI to speak in certain style. It’s still average but for the chosen style and thus less tone-deaf for a given use case.
So my thinking is - how much mileage can we get by introducing specific style guides? We can create a library of styles, and to get out of average for a specific guide individual companies and even people will maintain their own private patches from upstream.
Another option is to maintain history of your own writing and thus preserve your own voice. I feel like “averaging” of style is somehow un-ergonomic, in that in numbs the mind, and thus even diversity for the sake of diversity is valuable.