What does it mean to listen critically and sympathetically at the same time? I frequently see philosophers, other academics, and pundits listening critically but not sympathetically. This kind of listening is like ammunition gathering. The listener is indeed listening critically, trying to discern the speaker's meaning accurately, but only to criticize the speaker's argument. The listener's original intent is to poke holes in the speaker's argument.
On the other hand, the listener can have the original intent of creating shared meaning, for the sake of mutual understanding. This is when the listener listens critically, not to destroy the speaker's argument, but instead for mutual understanding. These listeners listen critically and sympathetically at the same time.
The difference is very important. Anytime someone tells you they are a critical thinker, you would be wise to find out if they are also a sympathetic thinker.