I also think trust is the single biggest issue here.
The more you trust somebody the more leeway you will give them in how they can express themselves to you, because you expect them to be honest and you assume that they mean well. You are more willing to interpret ambiguity favorably. From experience this seems to be a rather universal phenomenon. I often determine how I should express myself to people based on how much I think they trust me, and this approach seems to work well enough.
The more you trust somebody the more leeway you will give them in how they can express themselves to you, because you expect them to be honest and you assume that they mean well. You are more willing to interpret ambiguity favorably. From experience this seems to be a rather universal phenomenon. I often determine how I should express myself to people based on how much I think they trust me, and this approach seems to work well enough.