I've had to train literally hundreds of people over the various jobs I've had and it causes me to over explain in almost every conversation.

I got two tricks to figure out how much someone knows about a topic and encourage them to ask questions rather than lie just to avoid being a little uncomfortable.

First, I look for them to use vocabulary that I haven't already mentioned or if they seem to understand something just by using a couple words.

Second, I ask them to explain something early in the conversation to make it easier to ask if they don't understand something later. It's usually really simple, but it really does work to lower communication barriers.

I like to think it makes us feel more like equals trading expertise, rather than like I'm some authority talking down to them.

I hope this helps anyone

Yeah that’s good stuff!

Seems like you have your best shot if you make it seem like a lack of knowledge on a given topic is really safe. “Is this something you’ve nerded out on before, or not yet? Oh you have - cool, it’s pretty esoteric. Do you know enough to summarize it in a sentence or a few? If not I like to try to give my own high level before diving in.”

Something open ended in there gives you a chance to validate whether the ‘I know what that is’ was ego or truth.

That's the ticket, IMO. I start off assuming they know, then pause to ask "are you familiar with x concept?"

If they say yes and they really mean no, there's really not a lot I can do. But it seems to make people feel at ease when talking to me - I don't get called out for over explaining or infantalizing people this way.