Why some leaders are well-prepared for the text and underprepared for the people
I have watched this scene play out more than once.
A young church planter arrives fresh out of Bible college, sent out with a ministry philosophy still warm from the classroom and a hunger to preach. His study is covered in commentaries. He has three alliterated points and what he is certain is a show-stopping illustration. He steps into the pulpit — and proceeds, for thirty-five minutes, to preach almost entirely to himself. The congregation is present, of course. Physically.
I say this with affection, because I was once that young man. The enthusiasm those fresh out of Bible college carry is not a problem to be managed, it is a gift to be shaped. The love for Scripture is genuine. The preparation is often impressive. But the classroom that equipped them for the text left them underprepared for the people. They stand up to preach, but they have not yet learned to pastor.
What I have observed is not a failure of intelligence or effort. It is a failure of orientation. Young leaders have been trained to serve the Word. They have received less formation in what Timothy Keller called the other half of the task — reaching the people.
I never met Keller in person, but his books and online sermons shaped my own preaching more than I can measure. It was sitting with many of his recorded sermons that I began to understand what I had been missing in my own early years at the pulpit: the sermon is not primarily a vehicle for the preacher’s ideas. It is a service rendered to a specific people in a specific place. Until this conviction takes root, a preacher will keep stepping into pulpits to address congregations he has not yet troubled himself to understand.
Half a Task Done Well
Keller structured his book on preaching, Preaching: Communicating Faith in an Age of Skepticism, around two movements:
Serving the Word: the faithful, Christ-centred exposition of Scripture.
Reaching the People: the disciplined, pastoral work of contextualising that exposition for a particular audience in a particular moment. 1
Most Bible college students are reasonably competent at the first task. They have been trained for it. But Keller is clear: contextualisation is not a footnote to the preaching task. It is half the task.
The Apostle Paul understood this. When he preached to Jews in a synagogue at Antioch, he reasoned from the Scriptures and Israel’s history (Acts 13:16–41). When he stood before Gentile philosophers, he began with their poets and altars (Acts 17:22–31). Same gospel. Radically different approach. Paul studied his audience. He asked, before he opened his mouth: Who is in front of me, and what are they already asking?
Preachers can sometimes skip this question. They arrive with the answer before they have heard the question. And so the sermon, however exegetically sound, lands like a letter addressed to someone else — delivered, but never truly received.
An Identity Problem
The surface issue can have a deeper root. In The Freedom of Self-Forgetfulness, Keller described the toxic pattern of ministry driven by the need for validation: the preacher who is “desperate to prove yourself, or endlessly preoccupied with how you look to others.”2
For years, my first instinct after preaching was to turn to my wife and ask what she thought of the sermon — hoping, of course, that she would confirm what I had privately concluded: that Keller ought to have been listening to my recorded sermons, rather than the other way around.
When a leader’s identity is not securely anchored in Christ — in the verdict already declared over him at the cross — the pulpit becomes a place of audition rather than service. The sermon becomes a showcase. The congregation becomes an audience for the preacher rather than a flock to be fed.
Paul cuts to the heart of it: “For am I now seeking the approval of man, or of God? If I were still trying to please man, I would not be a servant of Christ” (Galatians 1:10). The cure for pulpit self-promotion is not better technique. It is a deeper experience of the gospel — the freedom that comes when the preacher’s standing before God is settled not by the quality of that morning’s sermon, but by the finished work of Christ.
Knowing the Congregation
Keller defines contextualisation as “giving people the Bible’s answers, which they may not all want to hear, to questions about life that people in their particular time and place are asking, in language and forms they can comprehend, and through appeals and arguments with force they can feel, even if they reject them.”3 This requires the preacher to study the congregation with something approaching the same rigour he brings to the commentaries.
Keller’s first pastoral call was to a congregation in Hopewell, Virginia, where few of his church members had attended university. He could not preach as he had been trained to preach. He was forced to learn to communicate to people whose lives, questions, and reference points were entirely different from his own. Keller came to believe that preaching fails to connect with the audience when it does not answer questions. 4 This became a key principle he would later build on in New York City.5
What This Actually Looks Like
Knowing the congregation is a conviction before it is a ministry technique. But convictions must be inhabited. For the preacher who wants to shift his posture — from orator to under-shepherd — there are disciplines that can begin to do that work.
Start with the passage and the people. The instinct is to open the text on Monday morning and spend the week moving from exegesis toward application. But there is another movement equally necessary: beginning with the congregation and working back toward the text. The faithful pastor holds both simultaneously — commentaries open on the desk, and the weight of real conversations in his heart. The coffee cut short by tears, the awkward silence after a service when someone lingers at the door but cannot quite find the words — these are not interruptions to sermon preparation. They are sermon preparation. Two questions are worth sitting with together: What is this passage actually saying? And: What are my people carrying and how does this text speak into that?
Develop the habit of diagnostic listening. If the preacher is to know his congregation, he must become a skilled listener — not the listening that is really just waiting for a chance to speak, but the attentive, unhurried kind that treats what another person says as genuinely important. Practically, this means asking better questions. Not just “How are you going?” but “What has been the hardest part of your week?” Not only “Are you reading your Bible?” but “What are you finding it hard to believe right now?” These are the questions that surface the real objections and fears that people bring into the room on Sunday morning. The preacher who has heard these answers carries something into the pulpit that no commentary can provide.
Bring the congregation into the study. Once the listening has happened, the sermon preparation itself changes. As the preacher works through the passage, he finds himself pausing to ask: What will my most sceptical hearer make of this claim? What will the person drowning in grief hear when I say this? A useful discipline is to imagine three or four people in the congregation while preparing — people with genuinely different lives, ages, and levels of faith — and to ask, for each of them, where the passage will challenge, comfort, confuse, or convict.
Preach to faces, not to the room. The preacher buried in his manuscript is not present to his congregation — he is present to his notes. The congregation can feel the difference. There is something that happens when a preacher looks up, finds a face, and speaks directly to a person: it signals that he is not performing a text but addressing a human being. The congregation needs to see that he is speaking to them — not executing a document.
Let the text change you before you preach it. The preacher must come to the text as someone who needs it, not merely as someone who will explain it. There is a kind of sermon preparation that is essentially academic — the preacher stands over the passage, analyses it, organises it, and packages it for distribution. Then there is another kind that begins on the knees. Before the outline is finalised, there is a prior question worth sitting with in prayer: Lord, what do you want to say to me through this text, before you say it through me to others? The sermons that reach people most deeply are rarely the most technically polished. They are the ones where it is evident that the passage has cost the preacher something.
Under-Shepherd, Not Orator
The scriptural image that reorients everything here is the shepherd. Peter commands: “shepherd the flock of God that is among you, exercising oversight, not under compulsion, but willingly, as God would have you” (1 Peter 5:2). Ezekiel 34:4 carries an indictment of shepherds who have failed in exactly this way — those who have not “strengthened the weak,” nor “healed the sick,” nor “bound up the injured.” The charge is not that they lacked theological knowledge. The charge is that they did not attend to the actual condition of the flock entrusted to them.
The paradox of congregational preaching is this: the preachers most eager to be heard are often the least heard, because they have not first listened. The most effective preachers, Keller among them, were great listeners before they were great speakers. They earned the congregation’s trust not through the brilliance of their rhetoric but through the depth of their attention.
The Gospel Changes the Preacher Too
The good news is that the very gospel leaders are called to proclaim is the cure for the identity problem that makes self-centred preaching so tempting. The cross says that the preacher’s worth was settled before the first word of the first sermon. There is nothing to prove. There is only a flock to love, a text to open, and a Saviour to make plain.
Jesus himself is the model. The Word made flesh did not come to be understood — he came to make the Father known (John 1:18). His entire incarnate life was an act of contextualisation: God entering human language and culture, in order to reach human hearts. “The Word became flesh and dwelt among us” (John 1:14) — the supreme act of a communicator who took his audience with complete seriousness.
The preacher is not the destination. He is a servant pointing beyond himself to the One who is. And the path from self-conscious orator to faithful under-shepherd is not primarily a path of technique — it is a path of dying to the need for applause, learning to listen before speaking, and trusting that the God who called him to preach will honour the faithful, unglamorous, congregation-shaped work of preparation that most people never see.
The pulpit is not a stage. It is a gift given to an under-shepherd, for the feeding of a flock, to the glory of a Saviour who, before he spoke a single parable, looked out at the crowd and had compassion on them (Matthew 9:36).
Timothy Keller, Preaching: Communicating Faith in an Age of Skepticism (New York: Viking, 2015), Part One (“Serving the Word”) and Part Two (“Reaching the People”).
Timothy Keller, The Freedom of Self-Forgetfulness: The Path to True Christian Joy (Chorley, UK: 10Publishing, 2012), 11–12.
Timothy Keller, Center Church: Doing Balanced, Gospel-Centered Ministry (Grand Rapids: Zondervan, 2012).
Keller, Preaching, 119.
Keller, Preaching, 127
Author: Damian Grateley
Copyright © 2026 by Damian Grateley: The Other Half of Preaching
