How To Listen Like A Pro With Oscar Trimboli

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TTB Oscar Trimboli | How To Listen

Great leaders are not only masters in realizing the team’s vision and implementing a healthy culture for all. They also know how to listen deeply and actively. Mitch Russo sits down with Oscar Trimboli, a man on a quest to create a hundred million deep listeners. He explains how he uses his vast network and award-winning podcast Deep Listening to build a strong community about listening in the workplace. Oscar gives a quick masterclass in leadership by discussing how to properly monetize a community filled with listening people. He also breaks down the most effective process of community building centered on letting your passions take the lead.

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How To Listen Like A Pro With Oscar Trimboli

Our goal is to help you be a better leader, inspire more people, create the passion your community wants, and profit from the experience. Some people have asked me why I created this show. The answer is simple. I want to learn from my guests and my audience how to effectively start, grow, nourish, and capitalize on a tribe. 

I believe tribes are the social experience that brings people together in many unique ways. I want to share that with you. I also want to hear from you. Tell me what you want and who you’re interested in hearing from. I would love to know what action you take after every individual episode. I would appreciate that. If you’re a coach, go to and download my book for free.

Now, on to my guest and his incredible story. It turns out that my guest is the host of an Apple Award-Winning podcast called Deep Listening. He’s also a keynote speaker as many authors evolved to become. Along with the Deep Listening Ambassador community, he is on a quest to create 100 million deep listeners.

I know you don’t quite understand what a deep listener is, but you will in this episode. He also believes that when leadership teams focus their attention and listen, they will build organizations that create powerful legacies for the people they serve today, and more importantly, for future generations. We are about to get a masterclass on how to listen. Welcome to the show, Oscar Trimboli.

Good day, Mitch. I’m looking forward to listening to your questions.

I’m going to ask you the first question, which is simple. How did this all start for you?

It started in a boring boardroom, a budget-setting meeting in April 2008 with 18 people across Sydney, Seattle, and Singapore. At this time of the year, it’s the final budget-setting meeting. The meeting is scheduled for 90 minutes. These meetings are known to go for three hours because you can’t leave the meeting without the budget being set. Something funky happened in this meeting. The meeting finished at the 70-minute mark. It finished early.

At the twenty-minute mark, my vice president in the room looked me straight in the eyes and said, “Oscar, I need to see you immediately after this meeting.” I don’t know about you, Mitch, but the only thing that was going through my head is, “I’m getting fired.” For the rest of the meeting, I didn’t listen to a single thing that was happening in the budget-setting process. It is probably why I got a 32% uplift in my budget, which wasn’t good, but we’ll figure that bit out later on.

I was thinking about how many weeks of salary I’ve got left in my bank account. As I said, the meeting finished early. It finished at the 70-minute mark. Tracy asked me to close the door. As I walked back after closing the door, she said, “You have no idea what you did at the twenty-minute mark, do you?” The only thing I thought is, “Awesome. I’m getting fired and I don’t know what I did.”

I sat down next to her and Tracy said to me, “Oscar, if you could code how you listen, you could change the world.” As profound a moment of listening as that was on Tracy’s behalf, the only thing going through my head was, “I haven’t been fired.” All this magical money that I had taken out of my bank account, I’m stuffing back into my bank account.

The only thing I could say to Tracy was I bloated something very primitive. I was like, “Tracy, do you mean code or code-code?” I was working at Microsoft as a marketing director at the time. She said, “We work at Microsoft, Oscar, code it.” Many years later, we’ve coded it into an online quiz, cards, three books on listening, a jigsaw puzzle game, and the Apple award-winning podcast. The only thing I know is the more I studied listening in the workplace, the less I know.

What’s astounding about your work is that you have defined and uncovered a layer between people that most do not know exists. The benefit of having done that is your process can bring richness into every possible human relationship. If I could, I would like to send you right now to Moscow and have you sit down with my friend, Vladimir. Maybe you could help us understand what the heck it is he’s doing there.

I was deeply affected by your work. The reason I wanted you on this show is because your work is bigger than the community you’ve built. In fact, the work is what draws people to the community. If you’ve been tuning in for a while, many times when communities form and the tribal leaders that I interview talk, they talk more about the community first. That’s fine. In this case, without the work, the community wouldn’t exist.

I’m going to tell you what my vision is of a tribe. From there, I would like to see if you could help me relate what you are doing to that vision. A great tribal leader or any form of community leader is a polarized individual. That means that they believe something so strongly that they deeply attract some and deeply repel others.

If you have this, we call this a manifesto. If this manifesto is clear, a great community tribal leader naturally attracts those people directly into his or her community, and that starts as a passion. That passion is a magnet. That magnet draws exactly only those who belong directly to the community. Tell me from that perspective about your community.

A little commercial break before we do though, think about what you’ve described in the context of Vladimir Putin. You have some interesting insights there all by yourself to understand his motivations as well. In terms of our community, our communities have grown very organically. The Deep Listening Ambassadors named themselves through the podcasts that we were doing. I would get emails from people saying they wanted more connection, not only with me, but they wanted a connection with other listeners. They wanted a connection with other workplace listening professionals who wanted to improve their listening.

One thing I learned very early on as a good host makes everybody feel welcome, but a great host creates connections across the community. We host a regular monthly webinar where we talk about a theme. That will attract some people into the conversation but others won’t. It’s self-selecting. There’s no reason for people to attend these sessions other than if they want to improve that particular aspect of listening. An example would be how to listen during a video conference as a host and as a participant. That’s an example of what we do.

A great host creates connections across the community. Share on X

We’ve attracted people from Japan, Germany, Brazil, and all around the world. The strength of the community is the connections that they form during those webinars. Often they’ll go, “What have I got in common with an automatic car engineer in Japan versus a foreign language interpreter in Brazil?” They have listening in common, but they also have in common that they struggle with listening during video conferences as well.

I’m very clear that our community is about listening in the workplace. It’s not about listening as therapy. It’s not listening in life partnerships or partnerships that may exist in friendship networks. We’re very deliberate to say what we are about when it comes to listening. We refer others to amazing global leaders in the field of listening through therapy or for trauma all around the globe. That’s another thing I’ve been lucky enough to do.

If I were a tribal leader, I would be deliberate in finding other tribal leaders in adjacent fields in listening. Listening in a medical context, I deliberately don’t do work there. I exclude myself from that and I make sure other people do that. What I’ve learned as a result is the group itself brings its own energy and momentum. It generates its own outcomes and ones I’ve never anticipated. To me, the act of hosting that community and being deliberate about what we are about and what we’re not about is critical.

In the early days, I was vague about that. As a result, I didn’t attract that kind of people into the deep listening ambassador community. They named themselves. We did a little listening exercise, and they came up with their own name. These ambassadors say that with pride. I’m often shocked that people use that label themselves. That’s how our tribe comes together.

Did you write the book first? Did that then start to generate interest in your work or did you build the tribe and community first?

How To Listen is book number three in a series. In the early days, I remember this conversation with Dermot, a lovely Irishman. I was saying, “Dermot, I’ve been writing newsletters for two and a half years about world-class listening and I’m getting no engagement.” He said to me in a beautiful Irish accent, “Idiot, if you’re going to do something on listening, create a podcast.” I thought, “It’s so obvious,” but for two and a half years, it wasn’t obvious to me. What was obvious was the difference between hearing and listening is taking action.

TTB Oscar Trimboli | How To Listen
How to Listen: Discover the Hidden Key to Better Communication

I listened to Dermot and took action. I had no idea. With Dermot and a couple of friends in a hotel restaurant, we wrote out all the possible people we could interview for the podcast like submarine commanders, acoustic engineers, deaf people, blind people, foreign language interpreters, judges, journalists, and everything in between.

Once we started doing that, the momentum in the community came about. My clients and the community said, “It’s all great that you are here doing your workshop and all of that. You’re doing a keynote. When you leave, help us create something useful. Write a book.” Honestly, I never thought of myself as a writer, let alone an author. I just had all these stories in my head. The first book, Breakthroughs: How to Confront Assumptions, is about understanding what your listening filters are.

The second book is Deep Listening: Impact Beyond Words, and the third book is How to Listen. The process of coming up with a third book involved 2,500 people in our community. Half of those people we knew, and then we researched 1,000 people in a Survey Monkey panel that we didn’t even know. We researched the name, title, subtitle, structure and story.

There was this continuous dialogue going on with this community about the development of the book. It became a critical asset to me because I’m not a skilled writer, but they are skilled readers. They would give me very clear feedback, “Oscar, the story makes no sense. It’s rubbish. Oscar, this story resonates. Can you make it bigger?” It’s awesome.

A little commercial break from tech, we also listened to Amazon and Google search engines to make sure that the title we came up with not only worked for humans but worked for algorithms as well. Thus, the very literal title, How to Listen. That’s how the community and the content that we were generating play together.

The cards that we created came about in a workshop where we were doing sticky notes as an example. During the break, I was photographing the sticky notes to create an artifact after the fact for the workshop. As I was doing that, I was moving them around a little bit. Alice, whose card it was, came in and said, “Oscar, please don’t touch my card.” I thought, “This person is putting a lot of meaning into what they wrote there.”

I told that story to my editor, Kelly. Much like Dermot, she said, “Just make cards.” I was like, “Of course, let’s make some cards out of this as well.” They weren’t cards if you looked at them literally, but if you listen to what it meant to Alice, a card is what I should have created. There’s this symbiotic relationship between sharing the content, the community shaping your content, and making it enormously more valuable and better for the tribe than whatever I’m creating in the first draft.

How many people would you say are in your tribe as you can identify?

At a rudimentary level, there are 1,216 in our database that have that tag. You then go, “How many people are regularly opening emails? How many people are regularly engaging with the content?” It’s roughly 500 people who are regularly engaging in that. That’s a heavily engaged group. They’re not customers. They’re just people who are passionate about listening. We spend a lot of time around what you do in the book, Power Tribes, and 500 paying customers matter. For me, it’s like, “I’ve got 500 people who are interested in my content. I’ve just got to figure out how to get 500 people who are interested in my content and pay.”

We can work on that separately. Clearly, that’s a good objective. You mentioned that you do a webinar or a Zoom call monthly. Did I get that right?


Is there any other way that you collaborate with or communicate with your members?

The podcast itself is the primary asset. Once a month, we distribute an episode and survey them every year. We’ve completed the survey a few months ago. They’ve said, “Oscar, enough with the experts. We love the experts and keep interviewing the experts, but we need to hear from you doing a Q and A.” We did a little experiment with Shani from Japan, a principal in a school. She had a question and we answered that. The feedback from the group was like, “Please do more of that.”

The upside and the downside of podcasting is the only way you know people are listening is if they communicate on a different channel. There’s no way of knowing who has downloaded your podcast, but you know where they’ve downloaded the podcast and what time of day. That’s it. You don’t even know if they’ve listened. Podcasting is an act of faith.

TTB Oscar Trimboli | How To Listen
How To Listen: The only way to know if people are listening to your podcast is if they communicate on a different channel. There’s no way of knowing who has downloaded your episodes.


Sometimes, I sit there and scratch my head, and then I got a beautiful email from a military commander who’s about to leave the military in the United States saying, “I wish I could have heard what you say about listening when I started my military career because I’ve destroyed at least five careers for my inability to listen.” One of those being his own. Thanks, Andrew, for the LinkedIn message that you sent. There are ways we find out about that. The community of practice, as we call it, monthly goes into practice on a topic. An example might be how to listen in a budget-setting meeting. That might be another example of how to do it as well.

That’s great. I would say one of the goals of most people who build a community at some point is to monetize that community. Is that something you’ve done or are planning to do? If so, tell us about that.

Personally, I trade in three currencies. Money is one of them. Recognition is another, and impact is the third. It’s all about the legacy. In the early days, I thought, “Money for the tribe. That’s not the ethos of listening.” What I realized very quickly is those who value the work are willing to pay for it. As I think about the community in the longer term, I had a Zoom call with somebody in Israel who said, “Oscar, I’m ready. How do I take your Five Levels of a Listening model, Four Villains, quizzes, and everything you do? We’ve got some big listening challenges in Israel with our neighbors in Palestine, I’m keen to resolve this.”

Those who value the work are willing to pay for it. Share on X

In my mind, I was going, “I wish I was ready,” but I also know the broader the base, the higher the apex when it comes to building systems. At some point, I want to do that. Your book has created a wonderful scaffold for me to think ahead not only about what’s possible but what things I can do right now to put some things in place around procedures, documentation, and these kinds of things. Also, back to your point earlier on, by doing so and being explicit about it, I’ll start to attract and exclude different kinds of people as a result. I’m okay with that.

That’s the way the formula works. Many of us put free content out there. I have 550 articles on my own website. It’s all free. They’re all blog posts or interviews. What we expect to happen is we expect that some of that will be consumed and then some will float to the top and reach out and say, “I like what you said, did or spoke about. Can we have a deeper conversation?” All this stuff these days is necessary. More importantly, having an elevation strategy and putting people into a pathway that gives them the opportunity to do more with you by paying you and getting more of your attention is essential to any community that wants to sustain itself and continue to grow.

I’m speaking now not just to you but to everyone tuning in to the show. We all need to create a mechanism of supporting the community beyond the other two currencies, which unfortunately don’t pay for the website, internet bill, or put petrol in the car. It’s something to think about. That’s why I always ask this question in these interviews.

The other part of this is for those starting out. Some people have a product or a work that they want to get out into the world, and others don’t. They’re passionate. They have that manifesto that we talked about early on. From there, they create a product. For the audience, which path do you feel is best to eventually scale a community to the size of yours or bigger?

Are you asking about the sequence or something else?

I’m asking about whether should you have a product, service, or intellectual work before you start the community, or should you start the community based on your passion, and then evolve that work as the community itself evolves?

When we think about the social object theory of how you transmit an idea that sustains itself through a community, the idea needs to be easy to share. For some ideas, that’s going to be a product. For some ideas, that is going to be the manifesto, for example. As I mentioned, for two and a half years, I was writing about what world-class listeners were doing in blog posts and newsletters. Were they easy to share? Yes, they were. Were they salient and did they cut through? No, they didn’t because the value people put on an email is very different from a wonderful story where a client told me they were going into an elevator in the morning and somebody had their earphones on. They said, “What are you listening to?” They said, “I’m listening to this awesome podcast about listening. Let me send it to you.”

Most people think of a podcast as a product, and it is. It is a great way to transmit an idea very simply because you’re packaging it up in a way that can be shared but also is salient and cut through. The answer is it depends and it depends on where you are in that journey. Think very carefully. It’s not how well you communicate the idea. It’s how well your community hears it, and then what they do with that idea.

Sometimes, that’s very easy to do. “I’m going to forward your book, Mitch, to one of my clients.” That’s an example of me transmitting your idea in an easy-to-do way. Because you packaged it in a book, you’re making it easy for me. If I had to try and explain Power Tribes in a sentence right now, I do a very bad job of it, as opposed to the book, “Lisa, happy holidays.” It depends.

Think about this. You need to be able to simplify your message. Active listeners listen to what’s said.  Deep listeners notice what’s not said. Every Deep Listening Ambassador can say that phrase and do it because it’s the easy way to explain the difference between active listening and deep listening. That took me two years to figure out though. It wasn’t something I discovered very easily.

We evolve into our own practices. Even in our own intellectual property, evolution takes us hopefully to new places. I want to read something to you. It’s one of your cards. I told you before we started that I have been through your card deck now several times. There were a few that were very impactful, but this is the one that hit me almost the hardest. It was because I’ve experienced this but never identified it.

Your card is called Concept Time of Day. The explanation is your listening is like the battery on your phone. The tip is to notice when you’re listening batteries are full and when they’re empty. You then offer a way to recharge. You say, “Can you listen to music to recharge your listening batteries?” This is very profound for me because I’m an extrovert. As an extrovert, I am energized by people. What that means is that I’m always talking. I’m not doing as much listening as I probably should, but then I noticed in my own life that the tank gets empty. I never could quite identify that before.

For me, that was a profound moment when I saw that on your card. For the audience, these cards are magic. Oscar will share with us how you can get your own set of cards as well. The book is great too, but the cards are like the instruction manual for being alive. If you want to be alive with other people, you got to get the instruction manual, or else you’ll never get anything done. That’s how I thought about the cards. What do you have to say about that one thing that I picked out? What does that mean?

What we don’t realize is that focusing on the speaker is the wrong place to start your listening. You need to first focus on yourself. Most people aren’t even conscious of where their listening batteries are at. They turn up to a conversation with their listening batteries being red, yellow or touching on black that is about to shut down. The right conversation at the wrong time is the wrong conversation. If you can’t bring your presence to the dialogue, it’s going to be a bumpy conversation.

Focusing on the speaker is the wrong place to start listening. You need to focus on yourself first, and most people aren’t even conscious of where their listening batteries are at. Share on X

A skillful listener will choose, “Now is not the right time, although we scheduled it for now. I may need a five-minute pause.” I encourage people please stop booking meetings at the top of the hour. If there’s one thing I wish for the world is that everybody books their meetings not for 1 hour, but for 50 minutes because time is such an artificial construct.

My clients say to me, “Oscar, I so look forward to your meetings because I’ve got time to go to the bathroom. I’ve got time to collect my thoughts.” They have a very different conversation. It’s way shorter. Recharge your listening batteries can be as simple as drinking a glass of water or playing a song. Stand up if you’ve been sitting down. Sit down if you’ve been standing up. Walk outside and get some fresh air on your face.

If you can’t do any of those, take three deep breaths in through your nose and out through your mouth. All of those physical things will send signals to the parasympathetic nervous system that sits around your lungs and your heart and says everything is going to be okay, and then you’re available to the other person to listen. That’s why it’s so critical that you know where your listening batteries are at.

For me, it was a revelation. As I said, I was never aware I had those. I was aware of the results of not knowing that I had those. That card was a little bit of an emotional kick in the head, which was great. We’re at the point now where we’ve gone pretty deep into your topic, which I’ve enjoyed a lot. Everyone, if you’ve enjoyed this as well, I would like for you to tune into Oscar’s podcasts too because that is a wealth of knowledge, as well as consider grabbing a copy of his book and getting the cards. The last question I have for you, Oscar, is very simple. What does the future look like when you take what you’re doing two years into the future?

My vision isn’t about me or listening. It’s the impact of listening through the tribe or community and what they bring to the workplace. They’ll bring shorter meetings and fewer meetings. The world doesn’t need another meeting like it doesn’t need another plastic bag. We’re obsessed with recycling, yet we don’t think about the most precious and finite commodity that we have as humans, which is our time.

Also, people understand that listening can transform the person who’s speaking, as well as those around them. My wish is finally that more people are conscious that it’s more important to listen to what somebody hasn’t said than what they have said. This has implications for revenues, market share, profit and loss, employee engagement, profitability, cost, rework and quality. There are so many things that are impacted by listening if we could just pause.

It is more important to listen to what somebody has not said than what they have said. Share on X

I love it. That’s a great place to end this conversation. Before we do, I’d like for you to share with our audience something that you had told me that you had planned on doing for them. Tell me a little bit about what your idea is.

Rather than getting in touch with Oscar, I want you to get in touch with your own listening. Learn what the barriers to your listening are. Take the seven-minute quiz at and use the coupon code Powertribes. You will have access to the full paid 5-page report, including 3 specific tips based on the listening barriers that you can apply immediately in your next meeting. Thanks to Mitch, we’ll organize that. It’s normally priced at $20 to be complimentary to listeners of this show.

That’s a wonderful gift. I can’t wait to go there myself and take the quiz. I wasn’t even aware of that. Your website is very simple. It’s called Is that the primary website that you would like the listeners to go to?

That’s all about Oscar. I’d rather you learn all about yourself, so go and visit

This has been a pleasure for me. If you’ve enjoyed this show, I would appreciate a review on Apple Podcasts and even five stars if you think I deserve it. More importantly, share what you’ve learned here. Let us know if there’s something that struck you and made you think or feel a little bit different than you did when you started. I would like to know that too. Thank you again, Oscar. It was a delight chatting with you.

Thanks for listening, Mitch.


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