The Art of Questioning: How to Lead Conversations with Grace

Adapted from a script to our recent video.

Hello everyone! It’s Dustin with Name the Unknown where our mission is to disciple Christian men through shoulder-to-shoulder training in rigorous Bible study, apologetics, and evangelism.

In this blog post I will be sharing evangelism tips to better equip you to proclaim the faith of Christ to others.

Before we jump into these tips, I do want to note that the best way to learn how to do evangelism is to watch it being done and to do it yourself. Anything worth doing is worth doing poorly at first. So I want to encourage you not to wait until you feel like you’re perfectly prepared to start sharing your faith. Get out with another believer and just start doing it!

That being said, a small group of believers who I was doing street evangelism with in the summer, have decided that, during these colder months, we would focus on evangelism training and practice to make us that much sharper once we get back out on the streets. That has been fruitful and so I thought it may multiply the fruit to share some of what we have been going over in those trainings here online.

In this video I shared the first step in our training which was simply practicing active listening, summarizing what the speaker said, and then asking them “why” the speaker made a certain claim. This is a simple way to ensure we have the maximal amount of information to work with regarding what someone believes and that we do not misrepresent or misunderstand what they believe. This is the Socratic Method bread and butter: be genuinely curious and ask lots of questions—it’s a wonderful way to get the conversation going and establish a good rapport before you begin to challenge them.

What I’m going to talk about in this video is how to start leading the conversation somewhere. Curiosity and questions are great, but remember the ultimate goal of evangelism is to represent and proclaim Christ. In a book I’d recommend on the subject called Tactics by Greg Koukl—the author expresses a view that I share: you don’t need to feel pressured to get someone “to the foot of the cross” in every evangelism conversation. God is sovereign and our job is simply to be faithful ambassadors, ready to give a defense of the hope within us. That being said, we want to have the ability to guide the conversation to the subject of the cross if we have an audience who is willingly giving us their time and attention.

Ok, so let’s jump into it!

So the basic flow for a good Socratic conversation is initially to 1) listen, 2) summarize, and 3) ask clarifying questions. Let’s dig into some specific examples of ways to seek clarification, learn more about your speaker’s view, and push the conversation into deeper waters.

Here are some everyday comments you might hear in regular conversation:

• “I had a great day today.”
• “I don’t like my mom.”
• “I didn’t vote.”

What do we typically respond with in conversation to these kinds of comments? Not usually questions! Most people, most of the time, seem to respond with statements back—sharing a story for a story.

For example,

• “I had a great day today”—Glad to hear it! I did too!
• “I don’t like my mom.”—My relationship with my Mom is strained also. Parents are the worst.
• “I didn’t vote”—I didn’t vote either. Seems pointless, both candidates are bad.

A quick and easy way to make each of these responses better and take the conversation deeper is to simply ask “why”:

• Why did you have a great day?
• Why don’t you like your mom?
• Why didn’t you vote?

But there are other variations you could use too. Sometimes “why” can put a little more pressure on the conversation than you want, especially if it’s early in the conversation and if you’re not sure your speaker wants to go deeper. In that case, you could try something like:

• “Glad to hear you had a great day! What happened?”
• “Relationships with parents can be tough. Have you always had a strained relationship?”
• “I didn’t use to vote either. Have you ever voted before in the past?”

These responses include a phrase to relate to them or to affirm something about what they’re saying and then a question that is basically just inviting them to say more. This will help earlier in the conversation to feel out whether they are open to going deeper and allowing you to more directly challenge their thinking.

At this point it would be good to pause and recognize two things:

1. These tips are helpful in any kind of conversation, not just street evangelism.
2. These tips are abstract and are breaking down a conversation in ways that you won’t be breaking them down in your head when you are having a live discussion with someone. The point is not so much to give a step-by-step procedure here—my one goal with these tips is to give you confidence that you can have difficult conversations about contentious topics easily, casually, and with a calm and gentle spirit.

To summarize: the 3 initial steps to any good conversation are 1) listening, 2) summarizing, and 3) asking why and asking for clarification.

After awhile you will feel like you have gathered a sufficient amount of information about what your speaker believes on whatever your topic is. At this point you will be confident you can represent their beliefs accurately and fairly—you can say what they think and they would agree with you that what you’ve said is what they believe. Preferably you don’t only know what they believe but why they believe it.

Unless you have nothing to disagree with, it is at this point you will want to begin to get them to think about alternatives to their own viewpoint. This is where you begin to gently challenge them and ideally get them to consider the possibility that they may be wrong and why they may be wrong. The Socratic Method will again be an extremely useful and extremely easy tool here—challenge them simply by asking them more questions.

• Essentially, you are now going to make a statement, but phrase it as a question:
  • “have you considered…?”
  • “have you ever thought about…?”
  • “have you ever heard…?”

• For example, someone says “women don’t get paid as much as men, there’s a gender pay gap”.
  • Bad response: “Well actually that’s not true at all, there’s no such thing as a gender pay gap, that’s just made up by the liberal media.”
  • Better response would be: “Have you ever heard about how that statistic doesn’t take into account different job titles or length of time they have held their job”?
    • It’s a statement, but it’s phrased as a question. This is less combative, more conversational, and if you’re not exactly correct on something it allows them to contribute correction without it turning into a debate. And then it’s not embarrassing if you happen to have gotten something wrong.

• Another example: let’s say someone says “the Bible is made up, it’s all fairy tales!”
  • A bad response would be: “nuh uh!”
  • A better response would be: “Well, actually the New Testament, for example, was written by people who knew Jesus personally within living memory of the actual events it records.”
  • The best response though would be: “Have you ever heard how the New Testament came about? I’d love to share that with you, if not. It was written by people who knew Jesus personally…etc.” or “Have you ever heard about the fact that the New Testament was written by people who knew Jesus personally…etc.?”
    • Mind your tone, of course! If you ask your question with a snotty attitude the gentleness will be completely lost.

Now you know how to not only listen, summarize, and ask clarifying questions in order to know what your speaker believes. You now know how to start leading that conversation and getting your speaker to consider the truths you are out to defend.

In the next video (click here to subscribe to stay updated!) I will share how to wade through a longer-form monologue or rant that someone might give you. How do we respond when someone throws not just one claim, but a dozen claims at us? Subscribe and catch the next video to find out! I sure would appreciate a like and a comment as well to help us to romance the algorithm and get this content out to fellow believers who may need help in evangelism.

Thanks for taking the time to read, God bless!