The Collaborative Art of Listening

Blending curiosity, improv, and candor to help others expand their ideas

Jul 29, 2025

There are a lot of people trying to evolve their ideas into something big right now. Some of these people are shouting from rooftops, but most of them are quietly trying to shape their ideas. In this world of solo builders, fast moving technology, and a shift toward talking to robots all day - are we leveraging our opportunities to really listen to one another?

In recent years I've come to appreciate the art of listening as a collaborative act - one that, when done with care, can help influence and shape the ideas being heard.

Brenda Ueland wrote a short essay, The Art of Listening, that opened my eyes to just how powerful this can be:

Who are the people, for example, to whom you go for advice? Not to the hard, practical ones who can tell you exactly what to do, but to the listeners; that is, the kindest, least censorious, least bossy people you know. It is because by pouring out your problem to them, you then know what to do about it yourself.

... you then know what to do about it yourself. That's what we all want, isn't it?

Listening is a skill to be developed

I am not a naturally good listener. Over the last decade, I've put focused effort into improving. I've learned to be more curious, more quiet, and more interested in the needs, challenges, and objectives of others. I've studied ways to ask questions that get people talking, keep them talking, and rapidly build rapport. If you have worked with a good leadership coach then you've seen some of this in action. But there's more available.

Coaches tend to go only so far, their job is to keep some distance. They are there to help you explore your ideas without injecting much of their own. I've recently come to appreciate a more... entangled form of listening. Something more like improv, something more vulnerable.

The anti-pattern, the listening offramp

We've all had the experience of carefully weaving a story to pull the other person into our inner circle, to share the thing that we just cannot get off our mind. We hope they'll intensely validate our idea and go deeper on this journey with us.

They listen, quietly, and then when you finish they respond. "Yeah, I had a similar idea... let me tell you about it…"

And now the mic is theirs. The topic moves on, and the moment passes.

Crushing.

There's another way.

Three Techniques for Collaborative Listening

Yes, and…

Have you ever watched “Whose Line is it Anyway”? One person declares she is going to ride a jet ski, and without hesitation the other person becomes… a jet ski. Improv is all about expanding on the lead of others and never rejecting the ideas that come up. Improv is generative, producing ideas quickly - like rapid brainstorming - and it requires total focus on the situation as ideas emerge.

A key component of improv is the "yes, and…" - this idea that whatever the other person starts, you continue, you do not negate, you pull the thread and extend it along. You are saying “I agree, and let me expand on that idea with another thought”.

Applying this at work and as a leader

I stumbled upon this at work with a friend and co-worker, and realized we were doing something similar. We would begin to talk out an idea and the flywheel would get spinning in a way it didn't with other people. We moved fast through developing ideas, and it was expansive and generative, and the idea would blossom or hit a dead end more quickly than usual. What I noticed most was that we kept each other on task - we stayed with the idea - we developed it together. But it always started with one person sharing something new.

Here’s what this might look like:

A: “Hey, I was thinking about this idea yesterday… <describes their idea>”

You: “That’s really good, and if you took that a step further you could…. <add another angle>”

A: “Oh, yeah, totally - and with those things, you might be able to … “

You: “Nice, yes, and what about xyz? Could that add something here?”

In my post on Six Leadership Principles, I wrote about how I see listening today, as a collaborative act, based heavily on this experience:

Think of your own ideas as fuel for entering relationships, currency that you exchange for other people’s ideas, and in this process your ideas are consumed - burned in the flames of collaboration to become something else. They become a new idea that was only possible because of the chemical reaction that happened between two ideas that needed each other’s fuel to become great. The oxygen for this combustion to occur is curiosity - without it, both ideas remain potential energy that can’t ignite.

I've used "yes, and..." with others when they share an idea with me that I want to help them develop — it's a powerful listening tool. Once you begin modeling the behavior, it's very natural for the other person to follow.

Tell me more

Another powerful phrase is "tell me more" - this can be a statement, but it can also be a mindset. During one of these conversations, this statement rolls around in my head - like it's painted on the walls.

Tell me more...

When my mind distracts me with a response I want to inject, or an offramp from the present conversation I want to take, this statement brings me back. Tell me more...

This statement also gives permission when said out loud. It tells the other person "I'm here, I'm listening, keep going" - tell me more.

I use “tell me more” when it seems like the other person hasn’t completely unfurled their idea. I don’t like to make assumptions when I’m listening, and this request usually provides much more detail about what they are thinking, helping me follow their trail more closely.

What matters most to you?

The first time I was asked "What matters most to you in this situation?" I was stunned - I didn't have a response. I hadn't thought intentionally about what mattered most to me, and it took a fair amount of reflection to settle on a point of view.

We often move through life looking for external validation from others about our ideas - but what matters to you about your idea? Are you asking yourself that? Is someone else asking that question for you? Are you helping others think about that for themselves?

What's most important about this question is that it is asked, and that the thought process happens, not so much what the answer is.

I use this when someone has shared that they have options, and they seem to be looking for help weighing those options. Asking what matters most is a way of getting at what’s underneath their desire to pursue any of these options. What’s important? I also use this when other leaders ask for my help: “Happy to help, can you tell me what matters most to you about this?”

Advanced Technique: Naming the Elephant

There's an elephant in the room and it's hard to talk about. You think there's a lot more available to talk about if you could stop dancing around this topic, so you need to ask permission to name it - describe it - and get feedback from the other person about whether you are on track.

Name the thing: "I'm picking up on something, and I want to hear your perspective about what you would call it, but to me it seems like..." or "I'd like to say this out loud, and I would love to hear your perspective on it...". When you’ve opened the door on this topic - go back to listening.

This is still listening. You hear something worth talking about, and you need to steer the conversation toward opening that door.

I use this when I sense something going on that needs to be out in the open, and I want to make it safe to talk about. Be kind with this approach, if you confront the topic and there's still resistance - move along to something else. Interrogating is not listening.

Closing Thoughts

Some of the most meaningful conversations I’ve had as a leader have been as the listener, using these techniques and watching another person’s ideas blossom. In a world of increasing isolation, deepening every human interaction is worth your time. These techniques make conversations more interesting, they make you more interesting as the listener, and they improve outcomes for everyone you work with.

These techniques also translate in powerful ways to our digital interactions as well, bringing humanity to Slack conversations and video calls.

Lost is the way

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