The most useful question I know is also the most embarrassing one to ask: sorry, what does that actually mean?
It feels like admitting you are not clever enough to be in the room. In practice it is almost always the question everyone else in the room also wanted to ask, and it is very often the question that turns a vague answer into a real one. People reach for jargon when they are protecting something — sometimes a secret, much more often just the fact that they are not sure either.
The trick is to ask it plainly and then stop talking. Do not soften it, do not add “I mean, obviously, I know roughly what you mean” — that hands the answer back before they have given it. Ask, and then let the silence do the work.
I have never once regretted asking. I have regretted not asking a lot.
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