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lil · 4625 days ago · link · · parent · post: The Elegant Email: Suggestions on employing email as a pleasant conversational medium.
That is very very frustrating. Is it possible to make a guess and write him back, every time, saying "It sounds like you want me to watch that presentation. Is that it?"
or "it sounds like you're impressed by that. Is that it?" and then he says "Why don't you know what I'm talking about?"
"It sounds like my guess was wrong. Is that it?"
I actually have a whole list of sentence starters for these conversations: http://www.lilblume.ca/activelistening.htm whoops - that's for seeming empathic. but you get the idea. There's a similar one for seeming nondefenisve.