The first word of the Rule is, in Latin, "obsculta", a word that doesn't mean just 'listen', but also 'obey' (note, you'll likely find it in a Latin dictionary under 'ausculta' as I discovered after about 30 minutes of looking). Thus, the very beginning of the Rule puts into place a dynamic of listening and obedience. One, of course, cannot obey if one has not listened to the command given; perhaps we might also say that the practice of obedience also allows us to listen better.
I don't know much about music, but it has occurred to me that the difference between a good musician and a great musician is that a good musician plays the notes and the great musician plays the silences. That is, the great musician, in interpreting music, understands the emotional content of the pauses, of the gaps between the notes, and translates that into the expression of the music. The truly deep listening of monastic life is like that, in that it strives to not just listen to the words of the Daily Office, but to the silences.
This is a form of the 'via negativa', the ascetic approach to God that finds that the most true statements about God are those that deny what we think of God. Thus, when we say that "God is good" this is a true statement only insofar as we realize that 'good' is a human word that is unable to contain the true goodness of God. A more accurate statement is that God "transcends goodness" or "is not-good" -- not in the sense of being evil, but of being so far beyond any of our concepts of goodness that to say "God is good" is to say something that is ultimately false. At some point, the best we can do in contemplating God is not to say anything and rest in silence.
While reciting the Psalms and the other elements of the Daily Office, it is the silences built in which are the places where the listening occurs. The monks are broken into two groups facing each other and take turns reciting a verse or two of a Psalm. One group will say four or five lines and then wait for a response from the other group. In this liturgical dialectic we find the constant tension between listening and obeying. One group offers up the word of God for obedience and the other group listens in silence. I find myself concentrating on saying the words I am supposed to say, but perhaps a better posture would be for me to listen to the words I am supposed to hear. Perhaps I am so busy talking to God that I have forgotten to stop and listen to what God has to say to me.
One of the lessons of Benedictine monasticism is that it is in this silence that we can begin to truly listen, and it is in the presence of the silence and in the awe of the unspeakable presence of God that we can begin to truly obey.