29 Mar How To Ask Better Questions and Why It’s Important That You Do

There are few things that I enjoy more in life than a great conversation. I love people. I’m fascinated by understanding more about what makes them tick and how they view the world. In this way, conversations present me with meaningful opportunities to honor and value the ideas and experiences of others.

Great conversations also stimulate my mind and fuel my curiosity like nothing else. Conversational stimulation hasn’t been easy to come by during the pandemic. I’ve even heard introverts speak about craving more connection during this time. (To be fair, I’ve found that even during normal times connecting isn’t always the easiest, especially in such a sprawling city like Los Angeles. Connection requires intention.)

The fact is that most people I’ve met enjoy a good conversation. The majority of individuals I’ve encountered would also agree, either consciously or subconsciously, that a good conversation is one where they get to talk about themselves. I don’t mean this in a narcissistic way (at least not always). What I’m really getting at is that most people enjoy having their thoughts, experiences, and opinions validated in the form of attentiveness.

One of the easiest ways I’ve found to offer attentiveness to someone is through asking good questions. I don’t think I’ve ever had a great conversation that didn’t stem from a great question. Sometimes this question is implied. Other times the question is overt. 

In either case, my hypothesis is that great conversations consist of three things:

1. Great questions

2. Two or more attentive listeners 

3. The openness/ability to communicate one’s honest thoughts, experiences, and opinions. 

This idyllic conversational cocktail contains some ingredients that are in our control and some that aren’t. We can’t control whether or not another person is attentive. We cannot control another person’s ability to express themselves honestly. There is, at times, the ability to influence another person’s openness by our own, but this approach isn’t always reliable or appropriate. 

The aspect of the conversational equation that we can always control is the quality of our questions. The ability to ask a great question is a proficiency that can be grown, especially if you learn to notice a great question when you hear it… which begs the question: What is a great question?

1. A great question is open-ended.

It invites an essay-length response as opposed to a yes or no answer. Asking someone a binary question, such as if they like something, is easily answered with a simple “yes” or “no”. It is more of a quantitative question. Inquiring on a qualitative level, like asking why a person feels the way they do about a subject matter or how they came to feel a certain way, invites a much more insightful answer. It also gives us the chance to get a better understanding of the other person.

 2. A great question is honest.

Sometimes we ask questions in order to communicate how we feel about something. These types of questions might begin like “Don’t you think that… ?” or “Wouldn’t you agree…?” or any variation on this theme. This form of questioning often does more to communicate our thoughts than serving to inquire about the honest thoughts of the other person. Simply put, an honest question invites the honest thoughts, feelings, and opinions of the other person. It is a genuine inquiry, not a veiled statement.

3. A great question arouses thought.

In the spirit of evoking an honest response, a great question causes one to search themselves for that honesty. Great questions require us to think deeply about our position on the topic at hand. Oftentimes a great question forces me to consider something that I’ve yet to form a stance on. This consideration influences a certain level of cognition that stimulates engaging conversation.

4. A great question gets beneath the surface.

Our dive into the deeper levels of cognition brings us beyond the level of small talk into substance. We aren’t talking about the weather or sports scores. We’re talking about our opinion on the ethics of how climate change is handled in our country. We’re discussing our personal thoughts and feelings about how the 3pt shot has affected final games scores and whether or not we think it’s good for the future of basketball. These are much more interesting and enriching conversations in my opinion.

The ability to formulate these sorts of questions requires a certain posture. An effective question-er is attentive, asking questions with a genuine desire to understand. This desire often shows up in their body language. They are alert and focused. They make eye contact. Interest abounds. Learning is the goal. Pride is in the trunk and humility is driving the car.

In efforts to become a better asker of questions, I’ve decided to start a questions journal in my Day One app. Every time I hear a question that resonates with me, I’m writing it down for future use. Not only have these questions proved to be useful catalysts for great conversations, they are also incredible tools for personal reflection.

I learned one of my favorite questions ever from Andy Stanley. The question is, “In light of your past experiences, current circumstances, and future hopes and dreams, what is the wise thing to do?” Asking this question over the years has afforded me tremendous clarity and direction.

If you are looking to start a questions  journal of your own, here are 10 additional questions I learned from a friend at a conference I attended last year. He calls them the” unravel questions”:

1. Tell me something you used to be certain of.

2. What are you certain of now?

3. What is the meaning of life?

4. What is God?

5. What happens after you die?

6. If you could ask God one question, what would it be?

7. Tell me something you’re afraid of.

8. When are you the happiest?

9. What is one thing you believe that might surprise people?

10. What is one book or resource you’d recommend that has impacted you deeply?

Imagine the understanding and unity that would grow if everyone committed to asking good questions and being attentive listeners. It starts with you and me. Let’s practice together so we can get good at it.