I never really learnt to preach at college. Preaching was a subject, preaching was taught, but I don't think it was learnt. And I suspect that my experience was not unique.
One of the accusations I regularly hear is that we don't have enough application. I think this is generally true of Sydney preaching, but I don't think the answer is application. To come at this another way - what most people want in terms of application is not what they need. When most people say 'application', they want some practical outworkings of Christian living to implement in their lives.
The problems with that are several. Firstly, the Bible doesn't deliver a great deal of it. So if I preach that kind of application, I'll be exceeding the Bible's scope, and will leave it behind as the authority and content of my preaching. Secondly, if I present that as exhortation and suggestion, people are inclined to hear it as moral instruction and so take it on-board whether it is fitting for their situation or not. Thirdly, and relatedly, if I preach it as instruction and command, I will be preaching Law and not Grace.
Perhaps the best thing I've encountered on preaching has been listening to Clowney and Keller teach "Preaching Christ to a post-modern World." It's available on-line somewhere, and I've started re-listening to it. It helps you make sense of Keller's excellent preaching (ie, where it derives from), and you see how much he owes to Clowney (who is a real treasure to listen to and learn from).
Their tri-perspectival approach to preaching also is deeply fulfilling. I think I do only one of them well - expounding Christ from the Scriptures. The other two I am working on: applying Christ, and adoring Christ.
Applying Christ is basically, (a) getting to the roots of people's sins, and diagnosing those root-sins with the truth of the gospel. So, for example, this week the focus of the text is Jesus as our King, and so my application is to do some probing on the ways in which we reject God as King, and how that works itself out in our life and culture, and how Jesus as our King is in fact the solution to our problem. It's realising that the cure for our problems is always God and His Gospel.
Adoring Christ is something else I struggle with - hitting people emotionally with the vivid portrayal of the truth so that it engages our whole being and leads us to worship. This is really where illustration of truths comes in, and on the whole I'm not a handy creator of illustrations. Nonetheless, I'm working on it.
Will see how this goes this Sunday...