“You Ask Good Questions”: the Heart of an Effective Conversation

Recently, more than one person has said. “You ask such good questions. I want to be a person who asks good questions. What questions can I ask to engage my son or daughter? The women in my neighborhood? My counselees?”   This caused me to pause and reflect. How do you teach someone to ask good questions? I have found it has little to do with the right question, but has more to do with the heart from which the question flows.

What keeps us from asking good questions?

Instead of being others oriented we’re limited by our own insecurities.  I have nothing to offer the conversation. I don’t know anything about their interests and that intimidates me. I’m not smart enough. I’m too shy. I don’t have anything to say in response. I don’t know what to ask. These all reflect our propensity towards self-focused insecurity. We are consumed with who we are and what others think of us. This then creates a barrier for being present in conversation, an essential component for asking good questions.

Instead of engaging in the conversations that others are having, we become conversation turners. Comedian, Brian Regan calls it “the me monster.” That’s nice, but when is it my turn? Let me tell you about my experience, which is even greater or more horrible than yours. When are they going to ask ME a question? Our inner dialogue reflects our desire for the conversation to turn back towards our personal interest, experiences or personal needs. We long to find something in common, a shared experience to alleviate discomfort in conversation. We quickly end the conversation or find a way to change the subject according to our preference. Our focus on self and meeting our personal needs hinders asking good questions.

Instead of being present in conversation or in relationship, we honestly don’t care. We don’t have time to know more about whom they really are or what they do. We’re disinterested and we’re distracted, checking the score of the game or the latest post on social media, rather than doing the work of engaging in who sits among us. We have no interest in asking good questions.

Instead of taking genuine interest, we seek a formula. In the art of asking good questions, there is no formula. There are people. People created in the image of God with minds, bodies and souls. The key is having a heart focused on others:  a curious, open, selfless heart.

So what do real conversations consist of? How can we engage in meaningful ways?

Real conversations are concerned about others. One evening at our church’s covenant community group, I overhead a simple, yet profound question. One young man came and sat next to another on the couch. The first young man, with his arm around the other, asked “What’s on your mind lately?” The other proceeded with an effortless flow of thoughts and ideas. I thought, wow. What a good question. When was the last time I asked a question that invited one to open up so personally and freely? It was a question that went beyond our cultural “How are you?” It bypassed our usual focus on events and activities from the day or week.   These conversations are important, but they are limited. When we truly care for one another, we want to know how they think, what they feel, what energizes them and where their passions lie. It changes the question we ask.

Real conversations are intensely curious. We are not satisfied with knowing what someone has done or what they enjoy—we want to draw them out and invite them to go further. It’s the difference between information and insight. It’s the difference between sharing the activities of one’s day and sharing the highlights, disappointments and reactions to one’s day. Our questions can lead to broader, deeper places in knowing a concept, an experience or a person.

Real conversations include us entering in, to another’s life, culture, interests, experience. Paul called it “becoming all things for all people.” (1 Corinthians 9:19-23) Jesus modeled it by leaving His home and entering one that was disordered, chaotic and messy—a far reflection of His own image or creation’s original design (Philippians 2: 1-11).

To become more like Christ is to abandon our self-focused propensities. It is to lay aside our “wish dreams” that we expect from Christian community[i] for the sake of giving and serving another. It is to unite with another, take interest in another because they are a valued creation of our Heavenly Father.

Effective questions then reflect a curious, entering, selfless, pursuing heart that meets someone where they are, while desiring to be taught, influenced and shaped by each encounter. If our hearts are seeking His, He will inevitably shape our way of relating, including the course of our conversations.

[i] Bonhoeffer, Dietrich. Life Together: The Classic Exploration of Faith in Community. Harper & Row Publishers: 1954.