Discernment / Ordinary Life / The Skill

Winsome Series: Part 3 What Does Winsome Look Like?

At a recent conference for pastors I was amused during the Q&A session by how few questions were actually raised. It’s not that no one was interested in participating. There was a long line at the microphone in the aisle; so many, in fact that only a fraction had a chance to speak before time was up. What was amusing was that almost no one actually asked a question. Instead, they made comments, sharing a quote or telling a story or expanding on some point that one of the speakers had made. The moderator mentioned—more than once—that the hour was intended for asking questions of the speakers, but his reminders seemed to fall on deaf ears. A few of the participants asked questions, but most contributions were little monologues. The tone was that of proclamation rather than questioning, of seeking to instruct rather than being content to listen.

As I sat there, my attitude slowly shifted from amusement to irritation. I had paid good money to attend this conference, and the idea was to learn from the speakers, not hear every Tom, Dick and Harry pontificate about their latest hobby horse. My irritation turned into disgust, and I walked out. It was only later that I recognized my self-righteousness, and remembered that I, too, prefer proclamation to listening. Not only is asking good questions hard work, but sad as this is to confess, I tend to prefer almost anything I have to say, to anything you have to say.

There are other reasons why many of us aren’t good at asking questions. We have never practiced the skill, and so aren’t very comfortable with trying. Or we have a limited understanding of what teaching or mentoring or evangelizing includes. We imagine it to be merely a transfer of information instead of a dynamic process in which we walk alongside another person, helping them discover truth. And then there is the ever-present problem of busyness. Let’s face it: simply telling you what to think takes far less time than helping you think it through. Less effort, too. And I maintain more control over the conversation if we stay away from questions, since I can never be quite sure where your answers will lead us. It’s troubling for the discussion to wander off into areas about which I know little, or worse, have doubts about.

In Church on Sunday, Work on Monday, authors Laura Nash and Scotty McLennan are concerned that little meaningful conversation occurs between the Church and the business world, even though many on both sides desire it. And now because businesspeople are open to spiritual concerns in a new way, a host of programs and experts have arisen to address that need, but the spirituality taught in these seminars is seldom Christian in any meaningful sense. Though Nash and McLennan identify numerous reasons for the failure to communicate, and though there is culpability on both sides, one reason they identify is that Christian leaders don’t ask questions or listen. “Even among those who were enthusiastic about possibly creating a forum or other occasion to explore faith and work,” they write, “few [clergy] suggested that they were eager to hear what businesspeople had to say about their impressions of the tension they faced at work. Feeling they had seen just about enough of what business really cares for—consumerism, selfishness, careerism, insensitivity—they prepared themselves for lecturing, not listening.”

Windows into hearts & minds
Before we get too critical of those clergy, we should consider whether there aren’t times when we act similarly. Whether there aren’t situations in which we assume we already know enough about the other person to skip asking questions or listening, and simply get to the proclamation we want to give.

One place this weakness tends to show up is in our interactions with non-Christians. Our preference for telling rather than listening, of proclaiming rather than asking questions is one reason I think so many non-Christians find many presentations of the gospel to be unattractive and less than fully personal or engaging or winsome. Many of us think of witnessing as almost exclusively proclamation, perhaps with a few questions thrown in as a staged tool to launch the presentation. The questions can have the added problem of being duplicitous, in the form of a fake “survey,” the results of which are meaningless except to provide an opportunity for the witnesser to say what they intended to say all along. But even for those of us who eschew such techniques, asking sensitive, creative, and appropriately probing questions can be a challenge. Learning to ask such questions is part of learning to listen, and both are skills that can be developed and practiced, by God’s grace, as we seek to live winsomely before a watching world.

If we are to demonstrate the power and attractiveness of the gospel, we must exhibit a true authenticity as the people of God. Entering into a conversation with a non-Christian is not a signal to launch a technique, but a God-ordained opportunity to have a relationship with someone made in the image of God. People made in God’s image should be loved as we desire to be loved, by being listened to with care and attention. And because we live in an increasingly pluralistic world, among people who do not necessarily share our deepest convictions and values, asking questions and listening takes on added importance.

“We need to learn to ask questions that will help us understand the heart and mind of each individual we meet,” Jerram Barrs says. “The fundamental issue here is one of love. Do we care enough for people that we want to get to know them, so that what we say to them will be… a word fitly framed to touch the inner being of the unique person before us?”

That’s all fine and good, someone might object, but if the gospel is proclaimed, surely we can’t complain about that. There can’t be any harm in telling someone the truth, even if it happens to be in terms they don’t fully understand or appreciate. Not so, Barrs insists. “Evangelism that bypasses understanding runs the risk of offending people and turning them away from Christ. Such evangelism makes them feel treated without respect or discernment, just a number on the end of a sales pitch. Or they may sense they are being used to assuage our sense of guilt about not doing evangelism, or that we are doing some spiritual good work that will make God pleased with us but that shows no concern for them.”

There’s another problem with evangelism without understanding. It is contrary to the example set by Christ in the Scriptures. He didn’t treat Nicodemus (John 3) and the Samaritan woman (John 4) to identical presentations. Neither did Paul say the same things to the people of Antioch in Pisidia (Acts 13) as to the people of Athens (Acts 17). Both Christ and Paul knew whom they were talking to, and spoke accordingly. And lest we think that Christ, because of his divinity, and Paul because he was an apostle, came by their insight into their audience effortlessly, consider the text again. Both asked questions.

Willing to learn
Here’s an even more radical idea. As we ask questions of non-Christians, we must be prepared and eager to learn from them, not just gain ammunition or an opportunity for the gospel presentation that is to come. The conversation itself should have integrity. We are talking about having a relationship—whether briefly as we sit beside them on a plane or long-term as neighbors who can become good friends—with people for whom Christ died. And though they may know nothing of saving grace at the moment, they may, through God’s common grace have much to teach us about many things.

In the 1980s, Peter and Miranda Harris established A Rocha, a bird observatory and conservation center in Portugal. They welcomed strangers into their home, inviting them to help conduct field studies, enjoy the creation, and care for the earth. They began A Rocha because they are Christians and so take seriously the biblical command to care tenderly for God’s world. John Stott calls A Rocha “an exciting, contemporary form of Christian mission.” Yet, as we might imagine, things don’t always flow smoothly in such a setting. People come and go, and studies of migratory birds must follow the bird’s schedule, come what may. “Many of those who stay here are far more impressive and seem far more calm and coherent than we do,” Peter Harris writes. “Among our early visitors were a couple with three small children, unmarried Vegans with an unswerving determination to live sensitively in the fragile environment of the planet. It is quite a challenge to encounter such radical commitment. Their serenity was impressive, not least because at the time we were trying to cope with a particularly full house. [Their] quasi-Buddhist reverence was no path to God, although there were many things they could teach us.” Some-times, Harris says, Christian visitors would “almost begin a conspiracy” to influence the non-Christians to believe in Jesus. “We would have no part of that,” he says. “We have no option but to be honest about him and ourselves… I can think of many conversations with many people, and often they are in the form of an adventure, because genuine questions need genuine answers. By definition, if we are going to listen to each other, we do not know where the conversation will lead us. Our relationships with each other and those who stay with us can be taken at face value, and hold no hidden agenda.”

The community lived out at A Rocha is far from perfect, but it is a setting in which both Christians and non-Christians can come together, learn from one another, work together to care for and enjoy creation, and converse as those who bear God’s image. And because Peter and Miranda Harris and their staff are believers, it is a place where numerous people have come to look at birds but leave having seen both birds and the truth of the gospel.

Comfortable with unbelievers
There is an offense to the cross, but a grace-full life and manner of conversing is both warmly personal and profoundly attractive. That is why sinners flocked to Jesus.

Yet, too often followers of Christ are uncomfortable around non-Christians. We feel ill at ease, and unable to simply enjoy a conversation with them that is relaxed and personal. “Not only did he come from heaven to earth to make contact with mankind,” Stott says of Christ, “but during his public ministry he mixed freely with the world. He attracted sinners. They knew that he had come to call them to repentance and that his message proclaimed righteousness. Yet, far from being repelled, ‘tax collectors and sinners were all drawing near to hear him.’ He befriended them. He did not seem to be at all embarrassed by them; he was at ease in their company. His viewpoint was radically different from that of the Pharisees. ‘Pharisee’ means separatist. They would gather up their robes and recoil in self-righteous horror from the prostitute; Jesus allowed a prostitute to wash his feet with her tears and wipe them with her hair. The Pharisees had no dealings with publicans, regarding them as politically and morally despicable; Jesus entered publicans’ homes and ate with them. The Pharisees threw stones at lepers to make them keep their distance; Jesus stretched out his hand and touched a leper into health.” Christ never for a moment compromised nor did he ever withdraw. In fact, he was on comfortably intimate terms with the sort of people many Christians feel uneasy being around. “Are we like Jesus or the Pharisees?” Stott asks. “We find the company of Christians congenial and are uncomfortable in the presence of non-Christians. And in this we are poles apart from Jesus Christ.”

Though it is true that I might have more in common with a fellow Christian than with an unbeliever, discomfort and unease should not loom between me and my unbelieving friends. They too are made in God’s image, and like me, are sinners in need of grace. They are creative and significant, have much to teach me, and wrestle with similar questions, doubts, and fears. We would do well to become better conversationalists—and something good conversationalists all have in common is the ability to ask questions, a willingness to listen, and an eagerness to learn. Becoming more comfortable with these simple skills may make us more comfortable with people. Comfortable with conversations that are allowed to be natural and holy spirited. Including conversations with people who do not share our deepest values and convictions.

Skill in asking questions
By God’s grace all of us can develop skill in asking questions. Not as a technique, but as a true desire to listen, to understand, and to befriend. There are a number of ways we can begin to do so.

First, we should pray for grace that we might grow in the skill. And remember as we pray that we are addressing the Lord who asked questions and listened with care to the answers. Not because he was clueless about things, but because he showed love by conversing with people in a way that demonstrated his care for them.

Related to that, we could spend time meditating on the biblical texts in which God (in the Old Testament) and Christ (in the New) ask questions. What were the questions like, why were they asked, and how did they probe the inner recesses of hearts and minds? Helpful in this study is Dick Keyes’ lecture, “Jesus the Questioner” given as a workshop at the 2002 Rochester L’Abri Conference—an audio tape can be ordered online.

We can also learn from people who are good at it. Some have written books in which their giftedness in asking keenly-crafted questions is evident. Though as a postmodern philosopher he believes that the question, rather than any final answer is all that we have, Christopher Phillips has dedicated his life to leading thoughtful discussions. His Socrates Café is a lively exchange of questions and ideas about things that matter. Sharon Parks is similarly helpful in her book Big Questions, Worthy Dreams: Mentoring Young Adults in Their Search for Meaning, Purpose, and Faith. And don’t miss Steven Garber’s book The Fabric of Faithfulness. The product of a mind and heart deeply immersed in the truth of God’s word, Fabric not only teaches us about knowing and doing, it also demonstrates how a master teacher asks questions that uncover truth.

Better yet, begin to pray for a mentor who can demonstrate the skill. Attend a seminar led by Steve Garber or Donald Guthrie, two godly teachers who are especially gifted in asking questions. Seek to come alongside someone who is a comfortable conversationalist and learn from them.

We can also simply begin to actively trust God by asking more questions in conversations, whether with individuals or in groups. Over the years Margie and I have often covenanted together to “proclaim” less at the Bible study we were about to lead, and to teach primarily through asking questions. We’ve worked hard to develop questions ahead of time, and then tried to be sensitive listeners during the study so we could ask questions that prompt further reflection and discussion. And we’ve evaluated afterwards, seeking to learn from our mistakes and giving thanks when by grace we’ve been used to stimulate people to think in new ways. When we have someone over for supper, we try to ask questions to learn something of their spiritual pilgrimage, their doubts and ideas and hopes. These are small steps, perhaps, but they’ve helped us treat people as if they were truly made in God’s image. Be willing to be pushed outside your comfort zone. If someone’s answer to a question takes the conversation into an area about which you know nothing, relax. It’s a God-ordained opportunity to learn, to walk by faith, and when necessary, to say, “I haven’t got a clue.”

A few things are certain. It’s amazing how much you learn when you listen. It’s also amazing how cared for we feel when someone asks us a question and then really listens to the answer. And it’s amazing how the gospel is so rich and so deep that it addresses the reality of every person with their own ideas and values and yearnings. Not just in some general way, like a mortar shell lobbed in their vicinity, but like a sword piercing down into the recesses of their darkest secrets. They may reject that piercing, of course, but at least they won’t be able to dismiss it like they can the mortar shell, which is so impersonal and unspecific. They may even imagine the mortar wasn’t meant for them.

Learning to ask questions and listen, instead of simply issuing proclamations, doesn’t guarantee that the world will believe. It may make us believers less argumentative and more winsome, however. And for those of us who wish to be like Christ, that would certainly be a step in the right direction.


1. Can you think of a time you were taught something important by being asked questions instead of simply being told about it? How did it make you feel? How effective was the learning? Why do we find it difficult to ask questions? To listen?

2. Have you known anyone that was a gifted conversationalist? What was their impact?

3. Consider the quote by Peter Harris about learning from the Vegan couple that stayed with them at A Rocha. What is your response? Why? Also consider the quote about how they pursued conversations with those who came. What is your response? Why? Should we never have “an agenda” or “strategy” when talking to non-Christians? Why or why not? If you think an agenda permissible, are there any limits to this agenda? What would they be?

4. Several reasons were listed as to why we may feel uncomfortable in conversations with non-Christians. Can you think of others?

5. A Christian argues that in a conversation with an unbeliever, we should use the time when they speak not primarily to listen, but as an opportunity to prayerfully consider what we should say next, and how we can turn the conversation towards the gospel. Another argues that we don’t really have much to listen to, since at root everything is simple: everyone is a sinner and needs forgiveness. Just get the conversation around to that and present Christ. How would you respond? Why?

6. Do you agree with the notion that our faith will not be winsome to unbelievers if we are uncomfortable with them, or ashamed of being seen with them, or uncomfortable conversing with them? Why or why not? Consider the quote by John R. W. Stott on the example of Christ. Do you agree? Why or why not?

7. What plans should you make to develop skill in asking questions?


Church on Sunday, Work on Monday: The Challenge of Fusing Christian Values with Business Life by Laura Nash and Scotty McLennan (San Francisco, CA: Jossey-Bass; 2001) p. 130.
The Heart of Evangelism by Jerram Barrs (Wheaton, IL: Crossway Books; 2001) p. 234, 237.
Evangelism: Why & How by John R. W. Stott (Downers Grove, IL: InterVarsity Press; 1962) pp. 23-25. Under the Bright Wings by Peter Harris (London: Hodder & Stoughton; 1993) pp. 90-91, 95.