Matt Woodley: This is Monday Morning Preacher, a podcast for those who want to learn the craft of preaching. I’m Matt Woodley, editor of PreachingToday.com, and I’ve been a preacher for over a quarter of a century. That’s 25 years.

Kevin Miller: Wow, thanks for working out the math for us on that, Matt.

MW: That was my scintillating and I think very sarcastic guest host, Kevin Miller.

KM: Well, you can try to fire me but the people demand I be here to keep you in check.

MW: They would beat down the doors and drag me away. So about preaching, I mentioned that fact that I’ve been preaching about 25 years because I am still learning lots of new stuff about the amazing craft and calling of preaching.

KM: Yeah, me too.

MW: For instance, I was re-reading a sermon of mine from 12 years ago and it was based on Mark 8:34-38, where Jesus says, “Take up your cross and follow me,” and my outline went like this. Point number one, Jesus confronts the myth of comfort. Point number two, Jesus confronts the myth of safety. Point number three, Jesus confronts the myth of control. Conclusion, Come to Jesus for true joy.

KM: Are you looking for feedback on that outline?

MW: No. We did a podcast on feedback but that’s for other preachers, not for me. Actually, yes, that’s why I brought it up, because I don’t like it, so what’s wrong with it, Kevin?

KM: Well, I do like how clear it is. That’s awesome.

MW: One point for clarity.

KM: Yes. It does feel a little bit like the Jesus part of the outline gets tacked on at the end, so maybe something simpler since you’re essentially offering a problem solution dynamic. Maybe point one is our problem, point two is Jesus’ solution. So point one, we have these myths that make us feel good but ultimately they cause us to lose what’s most important.

MW: Yes.

KM: And the solution, point two, is you follow Jesus and gain what’s most important.

MW: Where were you 12 years ago when I really needed you?

KM: Where was I? I was working here at Christianity Today, laboring in obscurity.

MW: So today we’re going to talk about the fine art of outlining your sermon. There are a few fundamental points about outlines. First of all, any outline is almost always better than no outline. I have heard sermons that had absolutely no structure. It is like a human body without bones.

KM: It’s a bad mental image.

MW: So get thee a structure. Second, keep that structure as simple as possible given your text and your big idea. That’s your goal. I’ve heard outlines with three points, and then they had like three sub points, and then in the conclusion the preacher tried to smuggle in another point, and I thought, Ah, way too complicated. So keep thy structure simple.

KM: There you go with the King James English again. Well, my lord, can you give an example of a simple structure that you’ve used?

MW: I was preaching on the Emmaus Road and it’s a really complex text. There’s so much going on in there, and you could go a number of different directions and be faithful to the text. But I focused in on three words that those two travelers on the road said, “We had hoped he would be the One who would redeem Israel.”

So I focused on specifically on: “We had hoped …” I talked about how we all have broken dreams, and my big idea was Jesus offers good news for those with shattered dreams. My outline was simply two questions: “What is this amazing good news?” and “Who is it for?”

In that who is it for, I focused in on it’s really for ordinary people like these guys on the road to Emmaus. It probably wasn’t the most amazing outline ever, but I liked it for the simplicity given the text and the big idea.

KM: Yeah, one thing I would add about outlines is that they need some tension. Haddon Robinson used to say that when the tension is gone the sermon is gone.

MW: Ah, excellent. I love that. And our man Tim Keller, he said, “In your sermons you must build some suspense that creates an eagerness to hear what is coming next and a sense of traveling to a destination.”

KM: This sounds to me—and I’m guessing here—that you are subtly segueing us into a sermon clip from Tim Keller.

MW: We have a clip from the Keller-man.

KM: You are easy to read.

MW: No poker face. So straight from the PreachingToday.com archives, here is a sermon he gave on the book of Esther. This sermon actually focused on the villain of the story, Haman. Notice what he does to set up his outline.

Tim Keller: Haman is the most vivid and sustained case study in the Bible of everything the Bible says about pride and humility, and what happens to people who let pride rage unchecked. Therefore, it is very vivid, it illustrates so many other places the Bible speaks about pride and humility. We’re going to learn a lot. But I don’t want you to think this is hype when I say I really want you to listen because it might save the rest of your life. Not kidding. There are three things we learn here. First of all, the character of pride, what it is; the deadliness of pride, what it does; and the cure for it. The character of it, the deadliness of it, the cure for it.

MW: Now, not every preacher has to do outlines like Keller, but what part of that outline don’t you understand? It’s so clear: The character of pride, the deadliness of pride, the cure for pride. It’s simple, it’s memorable, it’s definitely based on the text.

KM: One thing I really loved is the way he builds his second point, the deadliness of pride. I mean, he takes the standard problem-solution structure and he makes it way more interesting by adding a middle section where he goes problem, complication, solution. That adds tension.

MW: In his preaching book, he offers a little outline that goes something like this: The intro, what the problem is, what the Bible says about this problem, here’s what we must do, and then what prevents us from doing this, and then he applies that to the human heart. So that’s his basic structure that he does almost every sermon.

KM: I came up with a simple way to remember that structure that I call hook, book, stuck, crux, meaning how Christ and the Cross is the solution for how we get stuck. He uses this a lot.

MW: That’s a great simplified version of that, really clear.

KM: Have you tried using this outline in a sermon?

MW: You know, I didn’t know that I was using your little four-word thing there, which is really brilliant, I really like that a lot, but actually I have. I was preaching on John chapter 20, doubting Thomas, just a few weeks ago and my big idea was Jesus welcomes and transforms the doubter. Basically, my outline went like this: We all struggle with doubt—that’s the problem. And I said not only Christians but non-Christians struggle with doubt, and Thomas is a case study of that. Then my second point was Jesus advocates for the doubters, and then Jesus challenges the doubters. Then there was a pastoral appeal to the doubters based on how Jesus treats the doubter in that text. That was my basic simple outline.

KM: That sounds like a great use of it. One of the things that Tim’s outline is very good for is confronting the idols of the human heart. So I think in your sermon you were really sort of confronting the human idol of certainty: I must have certainty or I will not risk anything, I will not trust. So that’s really good.

One of the things I’m realizing about outlines is it really helps to know which one to use for which text and which situation. So if I’ve got a text that really confronts the idols of the human heart—hook, book, stuck, crux, that’s a perfect one to use. On the other hand, let’s say my text leads me that I want to talk about a common everyday life problem and connect relationally with my people. Then I’m going to use Andy Stanley’s classic outline of me, you, God, you, we. Because what that does—and I won’t go into all of it right now, is it builds an immediate and relational connection with the listener and it sends them out inspired. It’s a great way to talk about everyday life problems. So different outlines for different purposes.

MW: I think you should just break that down real quick because that’s really brilliant too.

KM: In Stanley’s outline, the “me” means I share where I struggle with this everyday life problem. The you, then, you go, well maybe you have too and you give some examples of how other people may be struggling with it. God is obviously where you look in the Scripture for God’s wisdom on this. The you says, “Here’s what it could look like in your life if you applied God’s wisdom.” Finally, the we, you conclude on an upbeat note. You could say, “Imagine if every one of us took to heart this wisdom from God and applied it to say, how we deal with our anger. Wouldn’t our families be healthier? Wouldn’t our schools have fewer conflicts, our churches, our homeowners association?” This conclusion sends you out on an upbeat note.

MW: Yeah, that’s great. Now, I suppose if you did that every single week, 52 times out of the year, people might get a little bored with it, but it is brilliant and simple. Let’s say you’ve got an Old Testament text that requires some time and explanation. What would you do with that?

KM: For that I’d probably use the Joel Gregory outline approach where you go—then, now, then, now, then, now, three or four times throughout the message. That way I can explain the then, because the Old Testament world is quite a bit distant from our own. But if I do that for 15 or 20 minutes I’m going to lose my listeners. So if I go then, now, then, now, then now, it gives them enough energy and connection to their lives to keep with me until I’ve have had a chance to fully explicate that Old Testament text.

MW: That’s great. Well, let me give one final word to preachers out there about sermon outlines, and that is simply immerse yourself in the text and immerse yourself in prayer. I can’t say that enough. You don’t have to come and read the text and immediately get an outline. Most preachers do not. Keep reading the text, keep talking to the Lord about it, and then I believe after that time some kind of simple outline will come. It doesn’t have to be perfect, doesn’t have to be the only way to do it, but it could be one way to do it.

I was looking at a sermon on our site from Harry S. Wright, and he was preaching on Psalm 37. Go read it, it’s a great sermon, it’s beautifully written. It’s written by him as an older man, and you can tell this guy has spent time meditating on the text, reading the text, praying to the Lord about it. He came up with this two-point outline. Here it is: God’s plea, which is don’t fret, and then the second point is God’s promise, he won’t forsake us. So that’s it. God’s plea, God’s promise. You could tell that Dr. Wright had wrestled with that text, prayed about it, integrated it into his life, and he came up with that very simple outline.

So preachers, find some kind of structure for your text that is as simple as possible given your big idea and the text that you’re preaching on.

Timothy Keller is the founding pastor of Redeemer Presbyterian Church in Manhattan. He is also the Chairman & Co-Founder of Redeemer City to City, which starts new churches in New York and other global cities, and publishes books and resources for ministry in an urban environment.