Preaching Contextually: Navigating Your Cultural Divide

March 16, 2026

Speaker writing on blackboard during a sermon or presentation.

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.

I had the pleasure of sitting down with Tony Johnson, lead pastor at 2|42 Community Church, for the latest episode of the Better Preaching Podcast. Before we got anywhere near a sermon illustration, we spent a good five minutes on the vertical bar in “2|42” versus the humble backslash. Apparently there’s an etiquette to this. Who knew church branding had its own grammar police?

But once we got past my keyboard ignorance, Tony said something that’s been rattling around in my head ever since. He told me that when he arrived at 2|42, the phrase floating around the staff was “kill the celebrity.” Then he credited a wiser voice — Steve Larson — with refining it: it’s not about killing the celebrity, it’s about minimizing it. Because the moment any of us steps behind a pulpit, some measure of celebrity attaches itself whether we invited it or not. The question isn’t whether it exists. The question is what we do with it.

Now, Tony’s fighting that battle across seven campuses with a team of preachers. Most of you reading this aren’t. You’re the only voice your congregation hears, week in and week out, in a building where everybody already knows your name, your kids, and probably your car. So what’s the equivalent for you?

I’d argue it’s this: minimizing the celebrity in a small church isn’t about diluting your platform among other voices. It’s about refusing to let the pulpit be the only place people see you. It’s showing up in the hospital room without a sermon in your back pocket. It’s letting a deacon teach the text you were wrestling with in Wednesday night Bible study instead of saving every good insight for Sunday. It’s being willing to say “I don’t know” from the front row of a small group, not just the platform. The solo pastor’s version of “just another guy on staff” is being just another sheep in the flock who happens to carry the crook that week.

Tony told me he wants to sound the same in the pulpit as he does in a hallway conversation — no performance layer bolted on for stage lighting. In a church of eighty, there’s nowhere to hide that gap anyway. Your people know if Sunday-you and Tuesday-you are strangers. Minimizing the celebrity, for you, might simply mean letting that be true on purpose instead of by accident.

Because the gospel doesn’t need our personality to shine; it needs our honesty. When people watch a preacher wrestle authentically with a text, whether from a stage or a folding chair, they don’t walk away impressed by the preacher. They walk away believing they can wrestle too.

Give the full conversation with Tony a listen at betterpreaching.org.

Better preaching makes a bigger impact.

In 2006, Dave Stone stepped to the podium at the North American Christian Convention in Louisville, Kentucky. He had just become the lead minister at Southeast Christian Church following Bob Russell’s retirement, a transition that would have rattled most preachers into playing it safe. Stone didn’t play it safe. He preached from Ephesians 4 and asked a room full of church leaders a deceptively simple question: What is the greatest benefit of serving together?

He walked through three answers — unity, maturity, and testimony — and built the case that all three are real, but the last one matters most.

What makes this sermon worth revisiting nearly twenty years later isn’t the exegesis, though the exegesis is solid. It’s the storytelling. Stone understood something every preacher needs to learn: the right story doesn’t just illustrate the point. It becomes the point.

He told about his Uncle Greg, a quadriplegic with cerebral palsy, who went to a camp for developmentally challenged adults. A church member named John Miller volunteered as Greg’s counselor for four days, feeding him, dressing him, even rigging up a flotation device so Greg could swim for the first time in his life. At the end of the week, they asked Greg the standard question: What was your favorite part of camp? Greg raised his arm, pointed at John, and said one word: You.

That story does more theological work than a dozen propositional statements about humble service. And Stone knew it.

He closed with another story, this one from his own childhood. In 1967, his family was hit head-on by a hydroplaning car while on a trip in Illinois. His mother suffered a skull fracture. His father had twenty-one pieces of glass surgically removed from his eyes. Blind and alone in a strange town, the first visitor who took his father’s hand was an elder from a local Church of Christ. When Stone’s father mentioned that his congregation worshipped with instrumental music (a real fault line in the Restoration Movement) the elder said five words that carried the whole sermon home: That doesn’t matter. We just want to help a brother in Christ.

Stone admitted he’d forgotten that elder’s name. Then he landed the plane: I’ve forgotten the name on the back of his jersey, but I’m pretty certain what the name was on the front.

That’s how you close a sermon. You don’t explain the metaphor. You trust it.

Stone trusted it, and the room felt it.

Some pastors close out the year with an elaborate written review—pages of reflection, goals, and
spiritual inventory. Chris VandeLinde is not one of those pastors. By his own admission, his
December plan is Christmas Eve, a nap, family, and a lot of sweets. I respect the honesty.

But this past January, Chris—Lead Pastor of Cornerstone Christian Church in Shiloh, Illinois,
and my guest on this week’s Better Preaching Podcast—sat down and prayed a dangerous prayer:
“Lord, how do you need me to lead differently this year?” He’d just taken some hits in December,
the kind that felt personal and unfair, arriving right through the vulnerable chinks in his armor.
The enemy has good aim.

What God gave him fits on a sticky note, which is still stuck to his desk: thicker skin, softer
heart, tighter lips.

Thicker skin. You signed up for this when you said yes to leading a movement that calls
suffering gain. You cannot let an emotional attack from someone with no investment in your life
cost you two days of ministry. Be Elijah on Mount Carmel, not Elijah whimpering under the
broom tree.

Softer heart. Here’s the trap: thicker skin tends to harden the heart right along with it. Chris
insists those two must never run parallel. As the skin toughens, the heart should be softening
toward the broken, the hurting, and the far-from-God. Even the people pushing hardest against
you aren’t your enemy. God’s got a plan for them too. Ezekiel says He replaces hearts of stone
with hearts of flesh. That surgery is ongoing.

Tighter lips. Chris is a verbal processor. His words, though thirty minutes of conversation
confirmed it. God’s correction was simple: some things you work out with Me, not with an
audience. Not every frustration needs to be shared. Some prayers are meant to stay prayers.

I told Chris this sounds like the title of his first book, and I’m only half joking. It preaches.
Because most of us in ministry get the formula exactly backwards: thin skin that bruises at every
criticism, a hardening heart that keeps people at a distance, and loose lips that process every
wound out loud.

God’s order is better. Toughen up. Tender up. Hush up.

That’ll preach in 2026—and every year after.