Cultivating Intentional Conversations

Intentional conversations are often the key to to helping change people's lives. Spiritually intentional conversations deal with what's really going on in a person's life, and often help people see themselves (and others) more clearly. Author, counselor, and Pastor Paul Tripp illustrates this vividly through the following story: “My brother Tedd, who has always been a mentor to me, was riding home with me after a conference on marriage and family counseling. We were going about sixty-five miles per hour when he said to me, “You know, Paul, we probably should apply the principles that we learned this weekend to our own marriages. Why don't you start?” He then proceeded to ask me a series of questions about my relationship with Luella. I don't remember any of the specific questions, but I do remember the profound impact they had on me. It was as if God was tearing down thick velvet curtains that stood between me and an accurate understanding of my marriage. I saw myself with clarity, and what I saw wasn't pretty! Through those questions I watched myself do and say things I could not believe. Through those questions I finally understood Luella's experience and her frustrations. I saw my defensiveness and self-righteousness, and I saw that I had to change for the sake of the Lord and for the good of my marriage. Those questions were truly life-changing for me.”

Tripp recorded that story in one of his books on counseling, called Instruments in the Redeemer's Hands. What I love about that story is how aptly it illustrates the importance of asking good questions! Good questions are one of the keys to having a fruitful intentional conversation. If you can learn to ask people the right questions in a tone of voice that is inviting and not overbearing, it will be much, much easier for you to approach sensitive topics with others and also much easier to avoid having your friends or family feel like you are lecturing them. Although I should add, much also depends on your willingness and ability to be a good listener and not interrupt too frequently.

How to Have Intentional Conversations

Rule #1: Before you even start asking people questions, the first rule of thumb is this: people will only talk to you honestly if they trust you. Sounds simple and obvious, right? Sure, but ask yourself, “Am I the kind of person people would be willing to trust with the more intimate details of their lives?”

So what does it mean exactly to be a trustworthy person? The following list of questions might be helpful to ask yourself:

Do I often ask people how they're doing, and do I really mean it? Or am I just expecting them to say, “I'm fine” and move on with life?
Do I gossip about other people and share their personal news with others, or am I able to keep things in confidence?
Do I pray for others often? And do I pray with others often?
Do I genuinely care about other people's difficulties, or do I hope they'll tell me everything is going well so I don't have to face their pain or hard questions?
Am I able to give other people's burdens to the Lord in prayer, or am I weighed down by their sorrows or trials?
Do I share openly with others about my own struggles and am I willing to ask them to pray for me? This is key. People will feel more comfortable sharing with you if they know you are also willing to be vulnerable.

You don't have to be a perfect person before you can help others, but you should at least be aware of your weaknesses so that you can seek to grow in those areas.

Rule #2: Start at the surface and work your way down. To quote Shrek (the jolly green ogre of animated movie fame), “People are like onions. They have layers.” Don't try to get to the inner core before you've gradually worked at peeling back the outer layers. If you're just getting to know someone, it's not a good idea to start by asking them things like, “What's your biggest fear?” or “What's your greatest weakness?” or even, “How can I pray for you?”

Try to start with basic questions like, “What have you been up to lately?” “How is your family?” “What's new with you?” etc. Over time, as you get to know the person, you can start to introduce questions that are designed to go deeper, like, “What has the Lord been teaching you lately?” The goal is to get to know people well. As my Professor Ed Welch would always say, you want to know people well enough that you're aware of at least three areas of struggle for which they need prayer.

Rule #3: If you want to have an in-depth conversation with someone, choose an appropriate time and setting. In other words, standing in the church foyer at noon may not be the best place to have a long conversation about the struggles of the past week. Your friend is likely to be shifting his weight and looking at his watch because he's in a hurry to go home and eat lunch. If you want to go deeper with someone, set up a lunch date or meet her at a coffee shop. Setting is important, because people's expectations often heavily influence conversations. Most people do not expect to have deep conversations when they see you in passing, so it's best to save your more intentional questions for a time when they'll be relaxed and ready to chat.

Proverbs 10:20 says, Proverbs 10:20 says, “The tongue of the righteous is choice silver, but the heart of the wicked is of little value.” God clearly tells us here that wise and gracious words are invaluable. So don't be afraid to ask good questions. As long as you ask them graciously, most people will be happy to answer. If they're not, it may be because they're not ready to open up yet. If that's the case, just do your best to be a good and trustworthy friend. That in itself will speak volumes.