Listening to those you'll be speaking to is also of great importance. If you don't know the audience you're speaking to you're liable to speak over them, below them, around them, but not to them--let alone their hearts.
Consider the following words from Bonhoeffer:
The first service that one owes to others in community consists in listening to them. Just as love for God begins with listening to His Word, so the beginning of love for the brethren is learning to listen to them. It is God's love for us that He not only gives His Word but also lends us His ear. […] Many people are looking for an ear that will listen. They do not find it among Christians because these Christians are talking where they should be listening. But he who can no longer listen to his brother will soon be no longer listening to God either; he will be doing nothing but prattle in the presence of God. This is the beginning of the death of the spiritual life, and, in the end, there is nothing left but spiritual chatter and clerical condescension arrayed in pious words.
Youth leaders, perhaps more than most other types of ministers, must be listeners first. In counseling, no doubt, but also--and perhaps more importantly--in sermon preparation. What do the voices of the students say? What do they love? What do they hate? What are their struggles? What are the obstacles they face in life? What are the intellectual issues the students wrestle with?
If you speak only exegesis you speak what you have heard from the text, but you don't speak it in light of community. The role of the preacher is to speak what you have heard from the text in light the community you are speaking to. Speak the text, proclaim the text, but speak it to the heart of the community.
Tim Keller says that all scripture speaks to 'defeater beliefs.' Defeater beliefs are intellectual ideas that silence the compelling nature of the Gospel and quench of the work of the Spirit. "How can a good God let evil exist?" "Christianity is just a moral strait jacket!" and so on. Thus as you listen to scripture, listen to your audience simultaneously. What are the 'defeater issues' in their context? Do their social aspirations prevent them from embracing the Gospel ("What will they think at work or at school?"). Do they have intellectual issues that keep them from embracing the Gospel? The role of the preacher is to discern what 'defeater' issues the text speaks to and offer scripture's response to the congregation. This isn't merely apologetics this is the beginning of crafting a challenging word that pierces the heart.
For Keller, serving in Manhattan, he is constantly meeting people who have intellectual objections to Christianity (below is a great article he wrote that unpacks all of these issues). When he prepares his messages he seeks to listen to how the scripture is challenging the 'defeater beliefs' that so many Manhattan residents hold to. How does this Psalm challenge defeater belief: "Christianity is just a moral strait jacket," etc.
While Keller's audience is primarily well-educated and upwardly mobile and thus more likely to have intellectual issues with the Gospel. Most audiences don't struggle as much with intellectual issues as they do with social issues. In fact many sociologists believe that social realities are more of a factor in determining what a person believes than logic alone. A person is more likely to believe something if someone they respect believes the same thing. That said, the preacher must listen to the text as it, by God's Spirit, confronts social and intellectual defeaters.
Example: In High School many students constantly feel on the margins. They long to be accepted. This often makes them act out and 'pose' to gain acceptance into a certain group. This line of acting takes them farther from the Gospel as it pushes them to conform not to the will of God but rather to a certain social group. The Gospel challenges this 'social defeater' by maintaining that acceptance is not based upon 'posing' but on the basis of Christ. If you are in Christ you no longer have to anxiously seek to find acceptance, you are fundamentally accepted.
What are some social and intellectual defeaters of your crowd?
The challenging word of the sermon rests partially on how you speak to the audience's 'defeaters'. Discerning their 'defeaters' begins with an act of listening.