I’m pondering the possibility of preaching a few messages from Proverbs (very early days, it won’t be until the summer at the earliest). Since this is a very unique genre and even sub-genre, I need to start thinking well ahead. Here are some very early incomplete thoughts:
1. It is important to understand them in their historical context. These were sayings written in the context of a covenant that tied direct results to obedience or disobedience. While we continue to reap what we sow, we don’t live under the same conditions as ancient Israel. Somehow the preacher has to navigate this without making the text feel irrelevant.
2. There is more structure to the book than people tend to think. I have been impressed to see some explanations of structure in the apparently random sequences of proverbs (yet unless it really adds something, I don’t want my listeners to get bogged down in my inadequate explanation of that). I also think it is vital to understand the book as a whole and the role of personified wisdom and folly. I can’t just jump in and preach a verse here or there without taking time to consider the whole book properly.
3. Wisdom is a rare commodity today. The Proverbs call to pursue wisdom seems as necessary as ever. There is an amazing level of spiritual lethargy and applicational dumbness in the church today. Somehow I need to preach in such a way as to motivate the listeners to pursue the God of wisdom and to live out the wise teaching of His Word. Yet at the same time I mustn’t simply pile rules on rules and create a gospel-less sense of adding burdens to guilt-prone fleshly spirituality.
4. The pithy nature of the genre is powerful. So as a preacher who may often preach much longer chunks of text, I must resist the urge to pack information into the sermon, flatten the point and dissipate the punch. As a convinced believer in big idea preaching (a spoken communication commitment, as well as a recognition of the nature of inspired revelation), what more could I ask for than a powerful and memorable main idea already packaged and perhaps ready to preach? Yet it is so tempting to pack in information rather than pursue application and transformation. One truth driven deeper is better than multiplied truth scattered liberally.
That’s my thinking for now . . . gradually over the next months I will return to Proverbs and build toward a series.
Biblical Preaching 
I am glad to see number 2. Thinking through this when I preach on a text in Proverbs is very helpful.Waltke is helpful here.
1. Conditions are a lot more like old Israel than not – and that’s something you can show to help show relevance.
2. Jn 1:1 reveals that God is, among other things, described as a mind. The divine logos is the divine expression of thought – the mind that creates, sustains, redeems, and so forth. Personifying wisdom is a beautiful way of seeing God and seeing the image of God gifted to mankind. Ask for wisdom and God gives liberally (Jas 1:5).
3. Fear is the beginning of wisdom. Wisdom is missing because reverence is missing. With genuine reverence comes many things, not the least of which is Godly wisdom and the benefits of God’s grace, power, Spirit, and life.
4. Here’s an idea. Maybe have one reading from Proverbs each week with little or no commentary. Okay, maybe not. LOL. Many of the chapters of Proverbs are thematic. You can certainly select themes (let the Spirit guide you) and find specific Proverbs related to those themes.