Asking Good Questions and Listening Well

Updated: Jul 23

“How did it go?”


I’d gone to coffee with someone I didn’t know well but hoped to.


“It was OK,” I said. “She didn’t ask me any questions, so I felt like I had to carry the conversation.”


He sensed the discouragement in my voice and said what I was thinking, “Oh well. Maybe next time.”



Yes, maybe next time. I’m a pastor’s wife, so when I spend time with women and they don’t reciprocate questions, I chalk it up to women needing counsel or a listening ear, which I’m happy to give, and sometimes I can tell that they feel nervous or uncertain. However, I must say that a consistent lack of question-asking over a period of time spent with someone is a dividing line for me between friendship and casual acquaintance. Questions, I’ve discovered, are one of my love languages. But aren’t they for most people? Everyone wants to be known; everyone wants to be valued.


With the advent of social media, everywhere we turn these days we’re bombarded with people sharing their every thought and displaying their lives for all to see. People are shouting to be heard, and when they don’t feel heard, they shout even louder. Perhaps we are so busy shouting to be heard that there is not even the space to ask good questions, listen carefully, and think about what we’re hearing. Perhaps the art of asking good questions is dying a painfully quick death. Or perhaps it’s that we’re naturally good at talking about and focusing on ourselves and asking questions and listening requires thinking beyond our own desires.


I think it’s worth the effort, however, and not just because it fulfills a need within ourselves to know and be known. Asking good questions and listening well are key ingredients to fulfilling Jesus’ command that we love one another. This skills enables us to influence others and speak grace, hope, and life into the lives of others. Within the church, good questions and good listening kill the assumptions we make about others that often exacerbate divisions and gaps between us. How can we love and bear with one another if we don’t know and listen to one another?


Consider Job and his friends. Job’s friends showed up on his doorstep, sat with him silently for seven days, and then, without asking a single question, started spouting off counsel, all of which came from their own experiences and assumptions. If they’d only asked a few questions and listened well to Job’s grief, they could have comforted him and offered him hope rather than compounding it.


Job’s friends offer us “what-not-to-do” wisdom and in their lack of questions, we see more clearly that our goal in asking questions and listening well is not to gather information as a busybody might do or patronize the hurting but to develop or further a relationship so that we might serve that person in some way. So much can be helped and so much can be diffused by a simple question.


I’ve discovered the value of question-asking and listening well in my years of counseling education and in being a pastor’s wife. This is what I’ve learned:


Instead of making assumptions, ask a question.

There have been countless times that I’ve made an assumption about someone based upon my first interactions with them or their lifestyle choices and, when I began to ask them questions about themselves, those assumptions become completely shattered. This has taught me that it’s always best to try to get to know someone before jumping to conclusions about them based upon their job, their marital status, or their background. The best way of doing this is by asking them questions. I like it when people surprise me. Let people surprise you, too.


Lead with “What?” or “How?”, not “Why?”

If a friend approached you and asked, “Why did you do that?”, you would probably immediately get defensive. “Why?” questions do that. They also effectively end the conversation and, likely, the chances of any future conversations. “What?” or “How?” questions are more disarming and express a value and interest that you’re likely trying to convey.


Ask open-ended questions.

As a greeter at church one Sunday, I asked a guy and girl who were visiting if they were dating. He responded, “No, she’s my sister.” Whoops. I asked the wrong question because I made assumptions about guys and girls who showed up together, but I also could have avoided this by asking an open-ended question: “How do you two know each other?” Open-ended questions get people talking and give you material to work with as you move further into the conversation.


Move from the factual to the emotional.

This pertains primarily to a conversation involving advice-giving, but it’s always best to start with the facts: what happened, who is involved, and what was said. After the facts are laid out, move to the emotions behind the facts: “How did that make you feel?” When emotions are understood, the speaker feels heard, and they are then more willing to hear or receive counsel.


Listen where the speaker feels heard.

Asking good questions is important, but it must be paired with good listening or it’s pointless in showing value to the person we’re talking with. Our goal in listening is that the other person feels heard. To do this, we must pay attention with our whole body. Put away the cell phone, lean forward, look them in the eye, and give indication that you’re attentive with nods or verbal assents. Listen to what is said nonverbally. Follow with a response that encapsulates what they said, zeroing in on an emotion. It is perhaps most important of all, especially when the person is seeking our counsel, that we listen intently to everything and ask several thoughtful questions before offering our insight.


Have a few questions in your toolbelt.

These are some of my favorites in general conversations:

Tell me about your passions.

Tell me about what it’s like…(to be you, to do your job, etc.)


In regards to counseling situations, these are my favorite wrap-up questions:

If you could wake up tomorrow and it would all be better, what would that look like?

How do you see God working in this situation?

What is God saying to you about this situation?



Without question, if we work at the skill of asking and listening, we will see an opportunity of influence open up to us. People long to be heard and known and loved. Simply by asking careful and gracious questions and then listening carefully to the responses, we will have the opportunity to speak life-giving words into dry and weary hearts.