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We Must Learn How to Ask Expansive Questions

January 5, 2020

The idea of skillful questioning compliments my never-ending quest to become a better listener.

Sometimes a question is more than just a question. When it’s an expression of authentic curiosity, kindness, or genuine concern–it becomes more. Expansive questions have the power to heal and bring us together.

Krista Tippett, an American philosopher, in her compelling book Becoming Wise: An Inquiry into the Mystery and Art of Living, suggests there are three types of questions she deals with most often — simplistic, combative, and generous.

I want to keep honing both skills, each of which is a form of art. In most cases, I’m using the term “expansive” rather than Tippett’s “generous” word, because it feels even more inclusive and all-embracing.

Simplistic Questions

These tend to generate superficial answers.

By simplistic, I’m not referring to the mundane, everyday questions we ask, like: “Can you believe this weather?” or “Feels great to be on vacation, right?”

I’m talking about narrow but loaded questions that suggest the person asking already knows the best answer. These sorts of questions come across as condescending, implying that if you don’t agree, you’re an idiot. They may not even appear combative or offensive in that they assume, cheerily and innocently, agreement and compliance.

Questions like: “Don’t you just hate that?” “Isn’t she an idiot?” and “Come on now, where’s that pretty smile?” That last question, which in essence is a demand for a smile, not a question, makes me insane! I want to respond with a question around whatever deficiency they possess, like “I don’t know — where’s your hair?”

In essence, simplistic questions are statements masquerading as questions.

Combative Questions

These are usually black and white, automatically generate divisiveness, and create a stranglehold on existing positions and opinions.

“So, you’re saying I should just give up and let the bad guys win? Are you kidding? How can you think that?” These are combative, defensive questions that will either end a conversation or keep someone mired in a position they may be unable to defend but will undoubtedly be unwilling to explore further with you.

Sitting in a restaurant across from a dear friend who surprised me with his political perspective, I blurted, “Are you kidding me?” In hindsight, that wasn’t a question; it was a war cry to my friend. Luckily, our relationship weathered my smugness. From our subsequent discussion, I remembered that people always have reasons for their decisions. If we want to come together, we need to find ways to explore, and more importantly, respect each other’s reasoning.

Expansive Questions

Expansive questions express openness and a sense of curiosity that can create a surprisingly meaningful connection between two people, even when they have just met.

“Will you help me understand how you arrived at your understanding of that? Please tell me more.” Both are generous questions hidden within statements. They express a deep desire to understand someone and the topic they’re discussing more fully. Expansive questions can also reflect kindness and genuine concern. “How can I help?” “Are you being honest with me when you say you’re fine?”

When we engage in expansive questioning, that’s when a question becomes more than just a question. It becomes a tie that can draw us closer together. It tells someone we want to learn, understand, and grow from our interaction with them. And isn’t that what we all want more than almost anything? To be valued, heard, and deeply seen.

As a therapist, learning to ask questions that reflect my sincere curiosity isn’t a given. Just like anyone, I can fall into old patterns that tend to elicit responses that are as incomplete as my questions.

It Takes Practice

Despite my curiosity, there are still times when I need to revisit my intention to ask questions that call for exploration rather than agreement. When I’m not careful, when I’m on automatic pilot, my questions fall into one of the first two camps — simplistic or combative.

Expansive questions are impossible without sincere and patient listening skills. And the converse is true as well — we can’t experience genuine listening without expansive questioning skills. The two are inextricably linked, like the infinity symbol.

Is there a better way, other than a loving sexual encounter, for two souls to meet, see, and connect than when we are looking into each other’s eyes, fully present and listening?

My partner is a master of generous listening. At times, it makes me crazy because my deficiencies become all too apparent. I’m the therapist — I’m supposed to have this stuff nailed! I am grateful that sometimes I get what I need despite myself.

Generous Listening Is an Expression of Love

Expansive questioning and generous listening can help us navigate and stay the course when the going gets rough. I think we have it all wrong when we take it for granted that once we’re “in love,” it’s forever. It happens intermittently, and we must nurture it again and again. And I’m not just talking about romantic love. I’m talking about the love between parents and children and siblings, and also the love we sometimes feel for friends and clients and even relative strangers.

I suspect that it’s humanly impossible to remain in a state of perpetual love. But if we meet each other intending to ask more skillful questions and to practice genuine listening, it seems likely that we will more often connect in ways that satisfy and enrich us.

We Need Psychological Flexibility

People often come to counseling with some of what I call psychological rigidity. We all suffer from it to one degree or another. We make ourselves feel confident, or safe, or less afraid, by attaching ourselves to answers to questions that are unanswerable.

We say things like, “I believe that everyone should recycle, and people who don’t are just ignorant.” Or we reinforce our beliefs about who we are, ensuring that we will stay that way: “I am stubborn; always have been, always will be, that’s just who I am.”

One of my goals, for clients and myself, is when we complete our work together, we leave each other with a little bit more psychological flexibility and greater openness to ideas we may have previously rejected.
My heart’s desire, and overarching goal, is to abandon certainty and open myself to discovery.

Can you think of situations where you’ve found it challenging to ask expansive questions and willingly listen to answers that may not agree with your opinions?

Would you consider trying again with new questions that will take you into a conversation with presence, humility, and the willingness to abandon a belief you’ve been holding tightly?

What might happen if you meet someone you’ve been at odds with, and you ask, “Help me understand how you arrived at that conclusion,” followed by, “Tell me more,” instead of “How can you possibly believe that?” I would love to hear if it makes a difference.

Much love,


  1. I have a friend of my parents, also my friend, who shocked me to the core with her political beliefs. I was shocked because she professes to be a Christian. I did not ask her any questions at all. I listened while she expanded, quoting the Bible. I cannot remember how I ended my part of the conversation. I certainly wanted the conversation, or that topic, to be over. I feel, still, like a child when I talk to her.
    I am very aware that many Christians share her beliefs, despite Jesus having taught the exact opposite. I have journeyed and broken free of this conditioning, and my politics have changed radically during my journey. I know that her son, my good friend of my teenage years, also shares her beliefs, so I tend to bunker down.
    I guess I’m doing the opposite of your email! I’m overwhelmed by people whose views I have removed myself, rather than asking why or how they came to hold those beliefs.

    • Robyn says:

      What an awesome self-awareness!! Thanks for sharing your thoughts! When I write I’m writing to myself most of the time lol. Reminding myself who I want to be. Like my response to my friend when I said, “Are You Kidding?” It wasn’t helpful nor did it increase my understanding. I think that sometimes we get poked by others’ perspectives, and our reaction is just information that we’re scared of something. Maybe being overwhelmed by others’ beliefs? Something that’s helped me in some situations is to find one thing I can agree with. Just one thing. And when the conversation goes off the rails I can bring it back with a reference to the one thing we agree upon.

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