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It bothers me to hear this, because I know that I tend to fall on the "hard to talk to" side. I used to be really bad at this kind of resourcefulness, and I would have a hard time "chasing down" those various implications. I like to think that I'm better now.

I think that, as with many areas, deliberate practice has helped.

Can you specify how you did deliberate practice to overcome that weakness?

Just sit down and think not just about what a person said, but why they are saying it.

If my dad says, "Son, never date girls who are hippies", that probably means that he himself was burned from an experience like that. While reading it plain would have given me a catch-all theory that is not necessarily true, reading into the reasons told me two extra factoids: my dad doesn't want me to get hurt, and he has dated a hippie girl and that ended badly.

Someone told me once: "You're good at putting the puzzle together, but only when you have all the pieces."

I can't really give specific examples, but it really is a daily thing, where I remind myself to follow things to their logical conclusions, in order to know how to proceed with a task/project/question/etc..

If you know it, then that is half the battle won - as you say you've been able to work towards fixing it.

I honestly think most people like this have no idea that they are hard to talk with, or if they do they have not interest in fixing it, and just want to be left alone: The "I thought doing this job meant I didn't have to speak to people?" types.

For me it's not that I'm hard to talk to (I like to think?!), it's that I'm just not great at forcing a conversation. I think of this particularly in terms of VCs, like PG discusses.

I think I can handle most things, but the real detail of negotiating funding, or even being "forceful" enough in a first impression worries me.

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