The key is asking a related question that shows interest. Signaling that we are seeking relevant information rather than hiding it.
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To make our communications more effective, we need to shift our thinking from “What information do I need to convey?” to “What questions do I want my audience to ask?
Asking for advice is more effective, though, because it’s less overt. Rather than telling someone they’re great, asking them for advice shows that you hold them in high regard. That you think they’re smart and value their opinion.
Consequently, not only does asking for advice gather valuable insights, it also makes the asker seem more competent.
They responded to a difficult question with a related question of their own.
The more aversion there is to revealing certain information, the more important it becomes to ask questions that avoid making (positive) assumptions. Avoid presuming the absence of an issue.
But it’s not enough just to be direct. We have to be direct in a way that not only shows that we’re aware that there could be negative information, but that we are assertive enough to keep looking for it until we find it.