It’s easy to preach like a commentary. Either you lift content out of a commentary and preach it, or you write your message like you were writing a commentary. It leads to a set of headings superimposed on the text, and sometimes superimposed on a projector screen too. The Problem of Prayer, The Power of Prayer, The Perspecuity of Prayer. Or perhaps, Saul’s Condition, Saul’s Conversion, Saul’s Conviction.
This kind of outlining might suggest that the preacher thinks the greatest goal in preaching is to offer a set of memory aids to help the listener hang their thoughts in a biblical passage. It suggests that historical and biblical information is the key ingredient for life transformation. It suggests a lack of awareness of the possibilities for more pastoral care in and through preaching.
A couple of suggestions:
1. Try changing your view of “points” from titles to full sentences. A full sentence requires a verb and will more actively engage the listener than a title can.
2. Try writing your sentences in contemporary rather than historical terms. Whenever possible it is worth taking the opportunity to speak with relevance to the listeners. This can be done at the end, of course, but also in the introduction, in every transition, within each point, and also within the phrasing of each point. Make the point applicational and then support that from the text.
3. Don’t pour your energy into creating a memorable outline, but into effectively conveying the message of the text. When alliteration and parallelism falls into your lap, great, consider using them. But actually our energies will often be better invested in thinking through how to reconvey the already powerful message of the text, rather than trying to help people remember an outline. Lives are changed by the text, by the main idea, by the application of the passage, by connecting with God and with the speaker. Lives are not changed by outlines.
Biblical Preaching 
Ouch! Like a dagger in the chest! Aliteration comes so easy and natural that 98% of the time I don’t even think about it, it is already on the notes before I realize it.
I have for years tried to get people to remember the outline. For the record I have tried to present and drive home the main point of the passage. But I thought if they remembered the outline, they would remember the point.
You make sense, too much sense. I need to rethink my desire for my folks to remember the outline rather than making sure they remember and apply the main point of the paragraph or passage.
Thank you! A most enlightening post for me. I would like to see a couple of examples of sentences in historical settings.
Thanks for the encouraging response Gregg. An example of a historically set point might be as simple as “When David confessed his sin, God forgave Him” or “Paul instructed Timothy to treat fellow believers as if they were his own family.” These could easily, and more helpfully be stated as timeless or present statements (as long as they are true statements) . . . so “God forgives when sin is confessed” or “We should treat fellow believers as members of our own family.” Usually our exegetical work in a text will result in historically specific, past tense, descriptive statements. This is important, but we should try to preach present tense, contemporary applications of truth wherever possible. Having said that, with a historical narrative it may be better to keep some of the points historical in order to focus the application on the main idea (once it is revealed), rather than allowing points that are developing the telling of the story to become a series of moralised applications. Did I just create a need for another post . . .
Perhaps I may add a suggestion to help shy away from presenting a commentary? When it comes to preaching with visual aides, specifically PowerPoint slides, think of a title for the slide that is more than a heading and information. When you title a slide with a message, the audience doesn’t have to work as hard to understand your point. On a larger scale, by the end of a message, the auidience has a greater chance of understanding the unifiying theme of the text if the key points of the text are clearly stated as messages with your visual aides. Identifying the key informational points in the text is good, and bringing them together with a title that is a message rather than just information is great. Think about what message your title sends. Are your listeners overwhelmed with informational detail? Or are they ready to hear the underpinings of a key message?