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The thing which is natural to me is: when someone makes a claim, or gives me information, I intuitively think “what process led to them making this claim or giving me this information, and does that process systematically make the claim/information match the territory?”.

Ah, that's what trust is to me! That resonates strongly. I hadn't properly thought through the concept before. 

The big question floating around my mind is - to what extent should I let *this* kind of trust (or lack of trust) determine who I'm close to? 

[My comments are less refined than the main post, so take ‘em with a little extra skepticism. All the same, I think this might help.]

Sometimes people don’t want to talk, and that’s ok. But if the conversation turns into an interview when they do want to talk, a few different things could be happening.

- Some people rely too much on using closed questions. Using open questions instead can open up the conversation.

- Some people rely too much on asking questions in general. There are other types of things that we can say as the listener which may be worth using more of. Reflection of feelings (“It sounds like you’re feeling overwhelmed”) and reflection of meaning (“I’m hearing that this job really mattered to you”) can be surprisingly good, for instance.

- In general, the more attuned we are to the core meaning of what the other person is saying, beyond the surface facts, the less likely that the conversation will feel surface-level or like an interview. 

That's a big question. Some notes on what worked for me:

- The thing that has helped me the most was finding a volunteer role that involves empathic listening. It gave me a lot of chances to practice. Plus, because it was a new & separate space from the rest of my life, I was more flexible to intentionally choose the habits I wanted to cultivate there before old habits got locked in. I believe doing something like that would help a lot, though it is a relatively time/effort intensive thing to do. 

- If you don't have the time for something like a volunteer role, then there are other ways to practice. Having actual face-to-face practice conversations are very useful if you are in a position to do them. Therapy trainings frequently make use of role plays - they really seem to work for intentionally trying to build the right habits. Even without having access to specific trainings or people you trust to practice with, there are groups out there that facilitate the practice of empathy - I hear good things about circling (though I don't have a group nearby so haven't tried it), I've tried out NVC groups, I've practiced listening in therapy groups, etc. 

- If you know exactly what to do, but just forget in the moment, maybe trigger-action plans could help. Or having easy to see reminders written in your phone wallpaper/somewhere else prominent.

- If part of the problem is not being confident about what actions to take in-the-moment, the 'classic' author to read on empathic listening is Carl Rogers. Books such as 'A Way of Being' are great.