Preaching Contextually: Navigating Your Cultural Divide

March 16, 2026

Before he preaches, every preacher needs to ask: am I a generational native, or a generational immigrant? Each of us is naturally designed to preach to our own generational cohort. If you are a Gen X’er like me, you speak the language, you get the references. You are a native. But every other cohort? You might as well be a missionary in another country.

This five-part series of blog posts will explore five principles you can bring to your preaching that will more effectively help you communicate as a generational immigrant.

Preachers today face a cultural divide when communicating the timeless truths of the gospel to generations that are not their own. The first principle for effective preaching to a different generational cohort is to understand and embrace cultural differences by contextualizing sermons specifically for them.

Why Contextualization Matters

Contextualization bridges the gap between the biblical message and the lived experience of a particular culture or cohort. Scripture offers examples of this approach: both Peter and Paul adapted their messages to the cultural contexts of Jews and Gentiles.

Just as missionaries can communicate more effectively by immersing themselves in the culture to which they are called, preachers must study and understand the culture of different generational cohorts to connect meaningfully.

Understanding Context

Each generation is shaped by the experiences of their lifetime. Older generations may value stability, tradition, and loyalty. In contrast, younger generations often display skepticism toward institutions and authority figures, having been influenced by political controversies and religious scandals.

These realities shape their perceptions and their receptiveness (and resistance) to faith. Books like Generational IQ by Haydn Shaw and Engaging Generation Z by Tim McKnight can help.

Moving Beyond Assumptions

Preachers cannot assume their listeners share the same cultural reference points or spiritual background they do. The church no longer has a home-field advantage.

Today, preaching is an “away game,” requiring intentional effort to cross cultural and generational boundaries.

Practical Steps for Contextualizing

Here are four ways preachers can start to contextualize their preaching:

Learn listeners’ language and culture: Engage with their media, values, and experiences to understand what matters to them.
Be present: Spend time with people who are different than you—both in person and digitally—to build relationships and understanding.
Incorporate relevant illustrations: Your reference to that John Wayne movie might not connect. Use stories and examples that resonate with listeners’ context.
Address real-life challenges: Speak to the issues your listeners face, such as anxiety, financial pressure, delayed adulthood, or caring for aging parents.

By practicing contextualization, preachers can become cultural translators who make the gospel accessible, relevant, and transformative for everyone.

Standing in the Middle

March 9, 2026

“And the things you have heard me say in the presence of many witnesses entrust to reliable people who will also be qualified to teach others.” (2 Timothy 2:2)

My Biological Ancestry

My family’s American experience began ten generations ago when my seventh great-grandfather, Johann Jacob Weller, arrived in America in 1737. Four generations later, my third-great grandfather—Johann’s great-great grandson—moved to northeast Indiana. That’s where he and four successive generations of Wellers rest at Cedar Chapel Cemetery. It’s where they’ll lay my bones one day to await Christ’s return.

My Spiritual Ancestry

As fascinated as I am with my family’s genealogy, I am more intrigued with my spiritual family tree. I wish there was a good website for tracing the ancestry of my spiritual fathers and mothers.

I learned about Jesus from my dad, Larry Weller. My childhood preacher, a man named Jim Platner, led my father to faith in Christ. Jim tells me he became a Christian through the influence of, among others, a preacher named Hank McAdams.

That’s as far back as I can trace my spiritual heritage.

If Brother McAdams were still living, I’d be fascinated to find out who told him about Jesus. And who told that person. And the one before.

In eternity I think I’ll have all the time in the world to meet every person in that long line reaching all the way back to Jesus. Jesus discipled Peter, who told Clement about Jesus, who told Ignatius, who told Polycarp, who told Irenaeus, who told someone, who told someone else, all the way down the line to Hank McAdams, Jim Platner, Larry Weller, and eventually me.

Christians Stand in the Middle

That’s because all those folks lived according to 2 Timothy 2:2—“And the things you have heard me say in the presence of many witnesses entrust to reliable people who will also be qualified to teach others.”

If you’re a follower of Jesus, you’re called to stand in the middle between the generation who led you to Christ and people who have not yet become followers of Jesus.

Preachers Stand in the Middle, Too

In 2020 I began meeting with a group of younger preachers for coaching and encouragement. These guys ranged from their late twenties to early thirties, and each were first-time preachers.

By that time, I had been preaching nearly every Sunday for twenty-three years, so I had a lot to say. I’ll leave it to them to decide whether I had much to offer.

We talked about preaching. We explored leading in the context of a complicated time in our nation’s history (remember, it was at the start of the pandemic). Our topics ranged from the mundane—like how to prepare a sermon—to deeply personal subjects like how being in ministry impacted our wives and children.

As I move into my fifties, investing in the next generation of servant leaders feels more important to me than ever.

There was a slogan on the wall of the chapel at the college I attended: “God give us preachers.” This rallying cry is as relevant and needed today as it was forty years ago when I first read it.

It is a prayer, but it is also a reminder that I am the answer to that prayer, because I stand in the middle between the preachers who taught me and the ones who will pick up the mantle of proclaiming God’s Word to a new generation.

Evangelism is the responsibility of every Christian. But it’s important that preachers understand their responsibility to stand in the middle pulpit.

When Nice Isn’t Enough

August 20, 2026

I’ve listened to a lot of sermons in my day, and most of them I forget by Tuesday. But every so often a preacher says one sentence that just lodges itself in your chest and won’t leave. Jeff Walling gave us one of those at the 2006 North American Christian Convention, and twenty years later it’s still rattling around in my head: “The time for being nice is over. It’s time to be family.”

Let that sit for a second.

Walling, an a cappella Church of Christ preacher, was standing in front of a room full of Christian Church folks — instruments, praise bands, the whole works — on the hundredth anniversary of the year our two branches of the Restoration Movement got listed as separate religious groups by the U.S. Census Bureau. A hundred years apart, and he had the nerve to say what a lot of us have thought but rarely said out loud: being polite to each other isn’t the finish line. It’s barely the starting block.

He told this story about getting invited to speak at an instrumental youth conference decades earlier. He discovered, after several increasingly awkward phone calls, that “instrumental Church of Christ” was in fact a real thing. That night he sat stone silent on stage while 3,000 teenagers worshiped with a guitar. And somewhere around minute fifteen, watching all that unashamed praise, he realized the problem wasn’t the guitar. It was his own attitude.

That’s the whole sermon in miniature, honestly. Grace doesn’t just save you. It humbles you, it makes you holy, and then it makes you do the hard work of loving people you’ve spent a career keeping at arm’s length. Walling put it more plainly than I could: “It is not duty that drives me to do good. It is how good God has been to me.”
And then — I still get a little misty thinking about this part — he called Dave Stone up on stage, both of them preacher’s kids who’d buried preacher fathers, and traded Bibles with him. Right there in front of everybody. College presidents, seminary heads, worship leaders, all swapping Bibles like it was nothing, when it was actually everything.

I don’t know about you, but I’ve been nice to plenty of people I had no intention of calling family. Walling’s sermon won’t let me get away with that anymore. Nice is easy. Family is a mess. His words, not mine, though I’ve certainly earned the right to borrow them.

You can listen to the whole sermon on The Better Preaching Podcast. And you should. It’s worth every minute.

The Nod and the Shock

September 10, 2026

In the fall of 2016, yard signs started popping up all over Lincoln, Illinois. One neighbor had a Trump sign. Another had a Hillary sign. And squeezed between them, on lawn after lawn: “Jesus. Period.”

People assumed it was a political statement. It was actually a sermon series.

Ron Otto, my guest on this week’s Better Preaching Podcast, has preached at Lincoln Christian Church for almost twenty years—the longest preaching tenure in that church’s history. And those signs announced the most audacious thing he’s ever attempted from the pulpit: an eighteen-month journey through the entire Gospel of Luke, starting one December and ending two Easters later. He told his congregation, “Your pastor’s doing this because he’s courageous.” Then he did it. The church’s highest average attendance came during that series.

Why did it work? Ron credits a cassette tape.

Years ago, somebody handed him a recording of Fred Craddock teaching on what he called the nod of recognition and the shock of recognition. Craddock’s warning to young preachers went something like this: in our rush to say something nobody’s ever heard before, we hunt for obscure passages and clever angles—and we steal from our people the joy of the nod. That moment when a listener leans back and thinks, “I know this story. This is one of the stories of Jesus.”

But the nod is only half the sermon. The shock of recognition comes when the listener suddenly realizes the story is about them. They’re not observing the prodigal son from a safe distance. They’re standing in the far country holding the pig slop.

I’ve heard it put another way: every sermon needs amen moments and aha moments. The amen is the nod. The aha is the shock. Preaching that’s all nod is comfortable and forgettable. Preaching that’s all shock is clever and exhausting. But when familiar texts suddenly turn and look your people in the eye—that’s when the Word does its work.

So here’s the encouragement, preacher: you don’t need obscure passages to be profound. Ron seldom goes looking for them. Preach the stories your people already know, and trust God to spring the trap.

Eighteen months in Luke. Yard signs in an election year. A congregation nodding along—right up until the story turned and shocked them.

Jesus. Period.

Because better preaching makes a bigger impact.

Fresh preaching insights await.