Article

Curious Questions to Engage Skeptics

From the files of Tim Keller

Painting of The Incredulity of Saint Thomas by Caravaggio, 1602 set on an orange background

Heritage Images / Getty

Recently appearing as an appendix to Michael Keller’s article, “When They Trust Jesus But Not You,” these questions were written by the late Tim Keller as a practical tool for pastors, church planters, and everyday Christians who want to engage skeptics with wisdom and grace.

In an age where spiritual conversations can feel like debates to win or landmines to avoid, Keller shows how a humble, well-placed question can gently crack open the door to deeper dialogue on spiritual realities. Not clever comebacks or pre-loaded traps—just honest, curious questions, rooted in love for one’s neighbor and modeled after Jesus himself. Use them to spark real conversation over coffee, in small groups, or wherever conversations turn spiritual. Sometimes the best way to speak is to start with asking.

–Chris Poblete, Editorial Director for CT Pastors


Questions to Ask Skeptics

  1. What do you think is the biggest problem facing us today, and what can be done?
  2. Do you think it is possible to know if there’s a God? Why or why not?
  3. How do you determine whether an action is right or wrong?
  4. Tell me about the God you think I believe in.
  5. What do you find most compelling (or what do you like most) about Christianity?
  6. What are your biggest objections (or what do you find most implausible) about Christianity?

Also, here is a list of things you could try to do this week to engage your congregation:

  1. Schedule coffee with someone who has left the church or is inside of it but unhappy. Don’t defend, and don’t explain. Listen, ask questions, thank them for their honesty, and tell them you appreciate their heart in speaking to you.
  2. Review your last month of sermons and count how many times you used “insider” language that would confuse newcomers or skeptics. Seek in your next sermon to limit this language or explain it to those who might not understand it.
  3. Identify what people in your church are struggling with, and find ways to address it in your next sermon that centers Christ and uses the text appropriately.
  4. During your next Sabbath, take time to reflect on what Jesus means when he says, “I will build my church” (Matt. 16:18) and not “You will build my church.” How does that change your struggles?
Posted September 1, 2025

Also in this issue

One of the great crises in the church today isn’t just the fallout of leadership failures—it’s the growing disbelief that pastors can still embody Jesus’ good and cruciform authority. Most pastors aren’t building empires. They’re proclaiming the Word, seeking the kingdom, and quietly laboring for lives to change and the gospel to advance. In this issue, Michael Keller encourages and equips those who pastor and preach to the institutional skeptic. Matthew Z. Capps makes a case for a healthy vision of church membership wherein shepherds can actually shepherd their people. Pastors Hannah Miller King (ACNA), Jonathan Leeman (9Marks), Gabriel Saguero (Assemblies of God) and Hershael W. York (SBC) talk about what makes their church governance models work. Walter R. Strickland II writes on the current state of Black evangelicalism and the institutional tensions of discipleship. Tailored mental and emotional health insights—for the pastor and the congregation—come from Dan Allender, Carey Nieuwhof, James Sells, and Curt Thompson. The theme of this issue is anchored with an essay from Taylor Combs on why we venerate and vilify leaders, written through the lens of Acts 14, along with a conversation between Rich Villodas and Richard Foster on the role of the pastor’s own discipleship in the health of a ministry. A pastor shares his account of how, by God’s grace, something beautiful was replanted out of the ashes of Mars Hill Church. Last, there is a robust books section, complete with a practical excerpt and a roundup of pastors sharing the must-haves in their personal libraries. This issue of Leadership Journal will strengthen weary hands, offer timely wisdom, and cast a vision for ministry that is both grounded and hopeful—one that reaches the disillusioned and points to the ultimate authority worth trusting: the crucified and risen Christ.

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Timeless Questions, Timely Answers

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