The album art for Speaking of Listening features a person talking into the receiver of a phone, only, she is speaking at the listening end (and vice versa)
The idea is to have this sense of loss between what is spoken and what is being heard, a feeling of disconnection.
The opposite of the idea of communication, if you will. Information being lost or even going into the void, it being transmitted but not received at the other end.
Also the person doesn’t seem perturbed by this loss of communication, almost like they are okay with it, in fact might even intend it.