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148Deep Honesty
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Thanks for bringing up the comparison points of radical honesty and explicit honesty. It does seem like deep honesty is in between the two.

But the characterization of deep honesty that you've posited doesn't feel very respectful? It leaves space to patronizingly share things the listener doesn't want to hear, because you've determined that they're relevant. Our notion of deep honesty is closer to being grounded in a notion of respect, perhaps something like "being completely honest about information you perceive that the receiver would want, regardless of whether the information has explicitly been requested". Sometimes that could involve some leaving of trailheads, or testing of the waters, to ascertain whether the person does in fact want the information.

As to "when should this apply", it's maybe something like "when you're trying to cooperate with the other party". Of course there's still room for this to go wrong (in the first example you link it seems like the person was trying to cooperate with their boss, who didn't reciprocate), but it does seem like a pretty important safety valve compared to radical honesty.