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Good listening needs good questions

01 April 2021 | intuitive scholarship systems

When you learn from others, you learn about yourself. When you go deep with others, you can go deep with yourself.

Listening is only minimally about quietness. Really, good listening is about focused attention and digging in with another person to really hear their story. Listening creates deep learning, often in the mind of the person doing the talking.

When you listen deeply to another and ask a few good, relevant, open questions they end up learning more about themselves. Listening helps the other grow. And then you grow, too, because you’re present in the connected moment. It’s a collaborative, lifelong dance and this active listening is a key part of going deep into your potential.

Talking as service

I have always been a pretty good talker. I enjoy talking, it comes naturally to me, it helps me think. I guess I could take the label of “verbal processor”.

It has served a strong function in my own life and as such I’ve viewed it as a way to help others when they seem to be struggling. Talking has served, in part, as a form of generosity from me.

“Oh, you’re having [a situation] and you’re telling me about it? You must want my advice. Let me tell you some ideas!” However, I am learning again and again that actually people almost never want advice.

No advice, please

Usually people want to process. They want to work through [the situation] on their own terms, using their own strengths and current opportunities. The partnership they typically are looking for is for the listener to ask a good question or two, validate their position, or to just really, simply pay attention. (I will talk about validation another time–that is also key to good listening. )

Listening, I suspect, is hard for far more people than just me. Not everyone is a talker, but certainly not everyone is a good listener. I think that’s in part because listening is seen as a passive sort of silence.

Not empty

I made a resolution a few years back to “listen more”. Feeling very excited and full of possibility, I even named it the Year of Listening. I would finally let others talk and I would become the quiet, nodding sage I aspired to be: so much listening would happen.

The resolution never materialized because I kept getting swept along in the moment and forgetting about listening. In hindsight, I had thought of listening as an empty action, an empty vessel, a neutral state, and in doing so had set myself down the wrong path of disengagement [from talking]. I was trying to not-do more than I was trying to find a new action to do.

Talking mindset

What was I doing wrong?

Essentially, I was continuing to think about just myself—a talking mindset, perhaps—and how I could be seen as smarter/wiser/whatever. I hadn’t considered how I might connect or engage more effectively through listening.

Here’s how it went.

I would set out on my day thinking just try not to talk so much, or I’d enter a situation trying to take breaths and warn myself to let others speak. It never really helped. I’d forget, or get frustrated or excited, and bam, back to talking.

Removing talking

Instead of some simple negative activity like not-talking, I needed to add a positive activity to fill the behavior-space. It makes sense to me when I think about how habits work—you don’t just remove things from your life. Your trade things in your life. You make exchanges for the things that will serve you better.

It’s a more positive, engaging, and interesting way to actually shift some of the behaviors that can feel sticky.

What’s the value of the quality?

Just deciding to “listen” (be silent) did nothing for me. There was nothing meaningful about the goal: it was a task grounded in notions of what I “should” do to fit certain norms I aspired to: quiet people are mysterious/powerful/wise. (And sometimes insecure or withholding—it’s not always magisterial.)

I wasn’t connecting to why listening could be transformative or beautiful. I wasn’t connected to the value of listening.

Silence is only a symptom

Trying to replace talking with silence doesn’t work. It’s not an even trade.

And for what? Silence in a conversational setting does nothing other than allowing someone to carry on, which probably serves neither party. Being silent doesn’t account for how we help or add energy to others. (We can help without giving advice.)

I didn’t realize that I was just displaying the crudest form of trying to listen. Silence can be a symptom of many qualities, but it’s not the actual behavior of effective listening.

Listening more is questions

The shift started to come when I learned how to approach asking questions in a new way.

Questions feel to me like the rocket fuel of listening: they activate what the other person is saying into new perspectives. It allows the listener to become active and engaged.

If I focus on asking questions instead of waiting to talk, the listening comes much more naturally. I get to be active and participatory—asking deep or on-point questions—and I also get to listen because how else could I ask those good questions? It’s active: actively receptive. Yin and yang together.

Active receptivity

As I expected, listening is amazing. Listening is like reading, if a person was a book. Layers you didn’t expect can be revealed. Here’s the other amazing thing: people feel so seen and appreciative for others who listen deeply. It is a rarity, this active receiving of good listening.

Good listening creates a space between two people that has a power and honor to it.

In principle

There are lots of ways to do it, beyond what you might think. It takes practice for most of us to be decent at it.

Questions really help me stay engaged with the act of listening. Listening itself allows for all the realizations that one might hope for.

There are techniques that you can learn which go with this fuel. Questions have to be placed artfully. They are done with grace and space. Calm and courtesy.

Questions are not asked to show the asker’s knowledge, or to minimize the listener.

Questions are never a form of taking over the show and doing some kind of back-door conversational dominance. They are, more or less, a way of trying to find what what’s big or possible in the other person. They are a form of giving or building up of another, but in that giving we get gifts.

How to do it: the very basics of open questions

Good questions are open-ended and probe beyond the stated, obvious details of the conversation.

Open and closed questions

Closed questions are easy to answer. They are obvious. They can be answered with one word, or very simply. They don’t imply that the asker wants more.

Did you do it?
Can you get there?
Is that what you think?

Open questions don’t allow for one-word answers. They want more. They demand at least a bit of thought. Open questions want us to dig in and to share it in conversation. This a key part of why questions make for good listening.

How did you do it?
Where can you go?
What do you think?

An open-ended question just cracks more and more into the issue. Open-ended questions typically end with “what” or “how”. There is usually no simple or one-word answer to an open-ended question.

A note on “why”

“Why” also creates open-ended questions, but it can have an aggressive quality to it, if not stated well.


“Why did you do that?”


“What was your approach when you did that?”

The second question has really different vibes. “Why”, without genuine concern or curiosity or rapport, can feel like an attack. It’s a perfectly useful word, but you gotta remember how it can sound.

What for

I hadn’t realized that listening could take so many active stances. That’s not simple silence, no way! There’s so much information available!

Beyond just the open-ended questions, we can also consider what to listen for. Listening for feelings (how does that feel?), for blockers/stuck spots (what will you try?), for social or environmental factors (who can help you? where would be best?), or for patterns in what the person is saying—there’s a lot available to listen for.