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Listening is the key to effective communication. To be in a consulting field entails you to be dominant in figuring out the pain points of your customers to provide the right solutions, and that involves deep listening. Author of Breakthroughs and Deep Listening, Oscar Trimboli lays out the five myths of listening and how you can leverage it in your business. Having one of Apple’s Best Australian Podcasts 2018, the Deep Listening podcast, Oscar outlines the three tactics to clear one’s mind, to be more present, and to make conversations more meaningful. With a purpose to create 100 million deep listeners in the world before he leaves the planet, Oscar highlights the cost of not listening in financial services and the key to creating awareness and getting the message out there.

I’m excited to have Oscar Trimboli joining us. Oscar, welcome.

Good day, Michael. I’m looking forward to listening to you.

For those who aren’t familiar with your work, take a moment and explain what you do.

I’m completely obsessed with the commercial cost of not listening. For most organizations, they survey staff, they survey customers and they don’t listen to what’s being said because all they do is collect the information and don’t act on it. The difference between hearing and listening is the action you take. I’ve dedicated my life to creating 100 million deep listeners in the world before I leave this planet. As part of that journey to helping others understand the difference between listening in black and white and listening in color.

We’re going to help you to spread that message because it’s something that speaks to me. I consider myself or at least I try to be a good listener. I’m sure I don’t succeed all the time. Oscar, I’m interested because you’ve worked with organizations like Microsoft, OpenText, Pandora, Google and many other well-known organizations. Before you got into where you are, let’s peel back a few layers here together and explore what you were doing before you started getting into coaching, consulting and spreading this message.

I’m the son of two first-generation migrants from postwar Italy. My dad always told me, “You’ll never going to be the smartest in the room because some people are always going to be smarter than you, but you can always be the hardest working, Oscar, so study hard. The job that will never go away is the accountant. You study hard to become an accountant.” My dad told me that so that’s what I did. Unfortunately, while I was studying for accounting, I started working in accounting and discovered in the eighth week of my study that I have something called Dyscalculus, which means I’m dyslexic when it comes to numbers. It means I transpose numbers.

The difference between hearing and listening is the action you take. Click To Tweet

If you say nine one seven to me, I’ll write one seven nine down or something like that. All the best life plans that I had and my dad had for me all went out of the window. In that accounting firm, I was doing spreadsheets on A4 sheets of paper, some dating myself about how old I am. I was writing on them in pencil. My boss’s boss said to me, “You’re a hard worker.” He noticed that already. He said, “What do you know about computers?” I said, “Absolutely nothing.” He said, “Great. You’re honest and you’re hardworking. You’ll be able to figure out how these computers work.” I went through literally reading the manuals and installing accounting software in accounting firms.

That sent me on a path to installing, training help desk, creating marketing materials, working with product engineering teams and probably knowing too much about accounting software. I spent a decade and a half doing that. Somebody asked me to consider work in the telecommunications field. I’ve done a lot of work in product management. At this point in time, there was a mobile phone provider called Vodafone. It was in a world where SMS messages could only be sent to the people on the same network. You couldn’t even send SMS across networks, let alone cross countries.

We were trying to develop software that would use data. We had an early data system called Wireless Access Protocol or WAP. It goes at approximately 100 times slower speed than what you have now on your cell phone. We couldn’t do much. What I was doing consistently at all that time was listening to customers and understanding their problems a little bit more deeply. Microsoft was trying to sell phones to Vodafone at that time. They asked me if I’d consider coming to Microsoft and setting up their telephone division, which they didn’t have. It eventually became the division that bought Skype, which most people will be familiar with.

I remember Vice President Michael, he flew all the way from Seattle to Sydney, that’s a 24-hour flight and came into a meeting that I was hosting with ten executives. He walked into the room and he did something that I’ve never seen anybody do before or since. He sat down, stopped, paused and apologized. He said, “I’m sorry.” He took his cell phone out of his top pocket, switched it off, walked over to his bag, put it down. He said, “I’ve flown all the way from Seattle to be with you here. The most important thing I can do is pay attention to you.” Michael, what do you think happened with the ten other CEOs around the room as Peter put away his cell phone?

I’m sure he made an impression on them. Some of them probably likely followed suit and gave a lot more attention.

Seven out of ten put their phones away and the other three probably put them on silent. The conversation was extraordinary in that room because everyone was paying attention. Peter then left and went on to his next meeting. He was taken away by another host and I did debrief with this team. They were a group of CEOs that are running companies of five, six, ten and some of them 25,000 employees. Their reflection was that’s the first meeting I’ve been in Microsoft that we didn’t talk about technology. It was probably powerful to not only listen to Peter but also listen to the problems of the other CEOs in the room. That was one of the many moments along my listening journey that went, “I can see how this stuff makes a difference.”

CSP 89 | Deep Listening


Oscar, with that in mind, everything that you’re sharing here with us so far, what have you seen maybe as some of the biggest opportunities for people to apply this idea of deep listening to their own business? For all the consultants reading, maybe from your experience, what do you think could they be doing better? What tactic, approach, principle or idea could they implement that would create greater value for them and for the clients they are serving?

The one thing I would say is to take this away from this podcast. If you are going to write down one thing, it will be this. If you were going to remember one thing, it would be this. If you’re going to apply one thing, it would be this. It’s the 125-900 rule. We speak at 125 words a minute, but we think at 900 words a minute. If you’re a consultant and you’re sitting across the desk from a business owner, what they say 125 words the first time is not what they’re thinking. They’ve got 900 words in their head and they can only say it at 125 words a minute. If they’ve got a Master’s or a PhD, it’s highly likely that’s up to 1,500 words a minute stuck in their head. One divided by nine is an 11% chance that what they’re saying is what they’re thinking.

I don’t know about you, but if I went to a doctor and said, “I need surgery,” and they gave me an 11% chance of success in surgery, I’d be asking for a second opinion. As consultants, we rarely ask the person we’re speaking to for a second opinion. We rarely use this phrase. If you remember the 125-900 rule, the phrase you want to get good at is asking the simple question, “I’m curious, what else are you thinking about on this topic?” They’ll say these coded words. When you hear these coded woods, you’ll be nodding while you’re listening to this. They’ll say things, “What I should have said was, do you know what’s critical, the most important thing we haven’t discussed is.”

Oscar, repeat that for us. The critical words that everyone needs to take away are?

They’ll always need to be prefaced by, “I’m curious what else you’re thinking about this topic.” They’ll draw in a deep breath, you’ll notice they will literally go, “Well, actually,” that’s one of the code words. Another one will be, “Do you know what’s important?” The third one is, “What I haven’t told you that I should have is.” What they’re doing is unpicking those other 800 words that are stuck in their head on that particular topic. Even a washing machine has two rinse cycles to get the dirty suds out of the washing machine. A washing machine for our thinking is our speaking. As we verbalize, we’re cleaning our thinking and the neural pathways in our mind are trying to connect in a way to verbalize the concept.

Most people don’t rehearse what they’re going to say. They’re not actors. They’re not radio announcers. They’re not TV news presenters. We as consultants need to help those people explore their thinking a little bit more. The critical thing I would say for consultants to discover more opportunity to what the barriers to buying are, to discover what the business case will be based on is rarely the first thing they tell you about. The most important thing they’ll say is helping them to explore those other 800 words. When we think about five levels of listening, we’re only talking about that’s an example of level four listening, listening to what’s unsaid. If all you did was spend time to explore what they haven’t said, you’ll sell more, they’ll refer you more and you’ll solve bigger problems for your clients.

We speak at 125 words a minute, but we think at 900 words a minute. Click To Tweet

You said there are five levels, that’s level four. Let’s go through the levels for everyone.

Level one is listening to yourself. Level two is listening to the content. Level three is listening for the context. Level four is listening to what’s unsaid. Level five is listening for meaning. It’s difficult to listen to somebody else if you’ve got a whole bunch of noise going on in your head from a previous meeting, another meeting, or the next meeting or an issue you’re trying to solve. Most of us struggle with attention, focus and distraction. That’s the biggest barrier to all of our listening. We focus too much time on the speaker. What we need to understand is if our mind is clear, we have a better opportunity to listen to all four levels above that.

What have you found as a way that people can effectively clear their mind? I’m sure it resonates with our audience where we go into a conversation, but our minds are consumed with something that happened previously, something that happened earlier that day or something that might happen in the future. What tactic, approach or mindset can people use to clear their mind, be more present, and ultimately make that conversation more meaningful?

Three tips, number one, remove all the distractions electronic. That’s the biggest barrier to most people listening. They have a laptop, an iPad or some device. If you’re using your iPad to take notes, that’s okay, but please take graphical notes. If you were to speak to Boris Konrad, the world memory champion, full-time memory champion, he would say to you, “If you’re going to take notes when you’re doing a client meeting, take graphical notes, you’ll remember them better. You’ll capture the essence of what they’re saying.”

If you take verbatim notes, meaning you’re literally writing some of the words they’re saying, the minute they get into the act of writing words, the neural pathway to the auditory cortex is shut down. That means in English, you can’t hear what they’re saying. No matter how good you think you are, you can’t multitask when it comes to listening, writing verbatim notes. If you have to take notes, take graphical notes. Boris Konrad and the techniques used by world memory champions, they use graphical notes. Tip number one remove the distractions.

Tip number two, always have a glass of water in a meeting both for you and the person you’re meeting with. If you drink coffee, then you’re going to have to have an extra glass of water because coffee is going to dehydrate you. A hydrated brain is a listening brain. The brain is 5% of the body mass. It consumes 26% of the blood sugars. Cognitively listening is a high load task for most people because we haven’t been trained. Only 2% of the planet has ever had any listening training yet it’s something we do for 55% of our day. People think listening is hard. If you drink water, your brain is hydrated, which means blood sugars get to the brain quicker and you’re set up for success.

CSP 89 | Deep Listening


Tip number three, the deeper you breathe, the deeper you listen. The more oxygen you can get to the brain, the better it will function in the process of listening. Make that practical for me is probably what you’re thinking right now. When I step through the lobby of a building, from that point on my cell phone switch to flight mode, it’s in my bag. As I go up into the lift, I’m taking five deep breaths and saying to myself, “What is my intention for this meeting? My intention needs to be about them, not about me.” I practice that breathing technique until I announce myself at reception. From that moment on, my state is changed because I’m not distracted. My focus is set by my intention and my attention is now focused on who I’m meeting next. I’m setting myself up to be a better listener because I’ve listened to myself.

For someone who’s not good at numbers, you’ve rattled off quite a few there eloquently. Thank you for that, especially people who have been listening to you. If you’re a longtime reader, you’re probably saying, “Michael, this is different than the typical interview that you do,” because usually, I’m diving in pretty quickly into how you got to where you are and how you built your business. We’re looking at marketing, strategy, sales and other areas. What you’re sharing here is important. I’m much with you in terms of the importance of listening. I see many people who aren’t good at listening or they allow distractions to consume them.

I’m thinking even in my time when I was in Japan, people always said, “Michael, how did you learn Japanese? How were you able to speak, to go into boardrooms, give presentations and win business with billion-dollar organizations?” It came from listening to what people were saying, whether I was at a bar, in a coffee shop or in a boardroom. Listen to what people are saying, their intonations, their dialects, the words they were using to allow myself to get closer and to understand how things were being done. This is applicable.

I want to thank you for sharing some of these tips. I hope that everyone reading this is thinking about “How can I apply this to my own business?” I do want to take us to a little bit more about your business because we’re going to make sure we have an opportunity to learn more about your work, your books and to dive much deeper into what we can’t cover. We’re going to make that opportunity clear for everyone but take us back. You worked at Microsoft. At what point did you decide to venture out onto your own and start building your own business?

It was a few years ago, a vice president said to me at the end of a tense complex meeting with lots of conflict between regions, global teams and the teams based in Australia. She turned to me at the end of the meeting and said, “If you could code how you listened for this room because you changed the way the meeting finished up. If you could code that, you could change the world. If you could code the way you listen, you could change the world.” I went, “Thank you.” I didn’t think anything of it. I obviously sat in my subconscious. A few weeks later, somebody said to me, “Not only do you listen to me, but you can also see who I am.” I went, “Okay, great.” They go, “Could you teach me that?”

I went, “I’m not sure what you mean, but let’s discover together.” We entered into a mentoring relationship. They helped me to explain what I was doing because they’d keep referencing back. “What did you do then? What was it that you noticed?” I said, “Your body energy changed. Your spine moved from slouch to erect. Your head tilt moved.” They went, “That’s what you’re doing. How do you do that?” That started a process for me. I also rebuilt the graduate program in Microsoft, which ended up getting taken at 26 countries around the world. I did that all through listening to the marketplace and the graduate community. Microsoft logo will get you into most conversations.

A hydrated brain is a listening brain. Click To Tweet

Your focus is deep listening. This is a sign that I would guess and many people may not necessarily be actively thinking about, searching for or maybe I’m wrong. Are people looking for help with listening? Is that something that they’re actively seeking out?

Here are three statistics, 86% of people think they are above average IQ, 84% of people think they’re above average car drivers and 82% of people think they’re above average listeners. The problem is most people think they are good listeners because they’ve never been taught. I don’t know about you, Michael, I didn’t have a listening teacher at school. You probably didn’t. Yet the teacher you remember the most is probably the one that listened to you. The problem of deep listening is a problem of awareness.

If you do the math in Google Trends and Google Searches, there’s a 200:1 ratio between people searching for speaking training versus listening training. The problem is a big problem of awareness for me. In terms of getting the message out there, it’s all about speaking in public events, setting up Meetup groups, speaking on podcasts. Spreading the word to raise the consciousness of the planet to go the way we’re listening now probably can improve if we spent the twentieth century going on training courses, learning how to speak with influence and persuasion. Maybe the leadership pack of the 21st Century is learning how to listen. That’s the journey out of Microsoft and into a journey of writing books about deep listening, creating a jigsaw puzzle about deep listening, creating a set of playing cards around deep listening.

I have a database of 1,400 people that is a three-year study of research around an application that I’ll create. You say to Alexa, “Alexa, for the next meeting, listen in and coach me on that 30 minutes after the meeting.” Alexa debriefs you and says, “Oscar, you interrupted at least four times in the meeting. Let me replay when that happened. You asked too many why questions. Explore what and how-based questions. He’s an example of how you might ask that.” As you focus, bear in mind there were nine people in the meeting, only three people spoke. Longer term to get to 100 million deep listeners in the world, it’s going to be through software for me. That question, Tracy, the Vice President posed to me, “If you could code that you could change the world,” that’s the journey I’m on now.

Microsoft or someone else will acquire that technology. You go full circle back. What I find interesting about what you’re sharing is a lot of people face a similar challenge when they have a belief around how to provide expertise or how to provide value to the marketplace. Oftentimes, the marketplace isn’t necessarily looking to buy or searching for that specific solution. I had a conversation with a client who wants to offer something to their marketplace. The marketplace isn’t looking to buy that specific offering. When they put it out, their messaging is around that, their website and their LinkedIn profile and everything talks about this one thing, but it’s not what the market wants. They’re wondering why they’re not generating a lot of inquiries or interest in their service offerings.

It’s because there’s a gap between what the market wants and what they’re focusing on. Back to what you talked about here, the way that you’ve tried to overcome that, or you are overcoming that is by creating awareness and attention through podcasts, through speaking. You’re putting in the work to get the message out there. Even though some people might say maybe you’re a bit early to the party, the message that you’re talking, what isn’t sign that people are currently searching for. You’re finding that by speaking, writing, getting out there that the message once people hear it, it’s resonating with them. Is that correct?

CSP 89 | Deep Listening


Yes. It’s taken me a few years to get there.

If there’s a way to shortcut that, and I don’t mean shortcut in the way there has to be a hack to do it, is there one or two lessons that you’ve learned along this journey for someone who wants to grow their business, has a belief or an idea, but maybe they’ve been facing some resistance in getting uptake with that?

It’s probably two things. Number one, are you narrow enough? When I learned that there was a coach in San Francisco who only works with autistic women in software development, I went, “That is narrow.” She has a monstrous global business because this is a tight-knit community, well-networked and refers her all around the world. If you have to put a label on her, she’s an executive coach. By super narrow, she was solving a specific problem, how do autistic women in software development communicate in a way that’s understood by leaders in their organization. That’s the problem she solved.

She put herself in communities where these people hung out and spoke to that problem. She didn’t speak to her solutions. She spoke to that problem. When I speak at public events, I speak at public events that discuss issues like employee engagement, market research issues for consumer-based organizations and B2B sellers and the cost of not listening when it comes to regulator engagement. That’s typically at a risk management conference and that typically covers things like the financial services industry, the transportation industry.

I’m putting myself in an environment where these problems are more apparent and the cost is more evident. I will always talk about the cost of not listening and frame it through a negative frame rather than going, “I’m going to teach you how to become an awesome listener because most people think they are an awesome listener.” 82% of people think they’re above average. I’ll run a poll in my presentations where people can vote off their cell phones and that no matter where I’ve presented that is consistent. It’s between 80% and 85% of people in a room of 100 people think they’re above average listeners.

When I talk to them about the full villains of listening, I talk to them about the dramatic listener, the shrewd listener, the lost listener, the interrupting listener, all of a sudden they’re engaged. They can relate to the negative implications of listening. Commercially, my message is always about cost and it’s always about negative consequences. That makes me easy to refer. I’m the listening guy, that’s how people refer me. You’ve got to get Oscar to speak. He’s the listening guy. You’ve got to get him in because this is different.

The problem of deep listening is a problem of awareness. Click To Tweet

If you’ve got a sales conference, he’s going to change the way people think about prospects. If you’ve got a kickoff with all the people managing a community, he’s going to tell you the difference between employee engagement and employee advocacy. We’ll teach the people managing community how to listen and where they’re failing. One of the steps between the research database I’ve got on that application I was talking about earlier on is setting up an assessment so people can assess themselves to know how bad they are. Commercially, that would be the next tipping point that I’m working on because the data is clear. I’m working with a university to prove the validity of the model that sits behind it. I think assessment tools people love and that’s a great way when you go in narrow to get people to go, “I’ve got that problem.”

For you to learn these speaking engagements or to get in front of these audiences, are you leading with the message around, “I’m the listening guy and I’m going to come in and talk to you about deep listening and how it impacts financial services?” Is the initial focus more on customer satisfaction or employee engagement as an example of financial services?

My positioning always is the cost of not listening and financial services are lost revenue, lost employees and customers who don’t trust you. We’ll always lead with their industry problems and then talk to how that is solved by listening. I rarely lead with listening although I’m referred to as the listening guy and I love that. When I remember my time at Microsoft, I didn’t have a budget line called listening. I didn’t have a budget line that would be easy for me to buy. I want to make sure that if their thing is they’ve got a budget line for training and communication training is how they would explain to me, that’s how I position myself in there. For a lot of consultants, you’ve got to think about, “Do they have a budget line for that? If they do, how easy are you to buy?”

I’m generally prompting a whole bunch of objections right up front before the prospect even says it. You must find it hilarious that you’re hiring a guy to speak about listening. How ironic is that? They all laugh and go, “Yeah.” How do you talk about listening and I said, “A concern for you might be that cynical Sam, the salesperson has been on all their sales training that you’ve provided for the last several years. I’m going to in the first five minutes punch him in the mouth and show him how poorly he’s listening because we’re going to go through a simple exercise around the full villains of listening. Which one do you think you are?” They immediately self-identify with the interrupting listener and they ask you for a tip. You give them a tip and away they go. You build a bit of trust.

I’ve always got to pre-empt a whole bunch of objections because people will know how to buy people who speak on topics of how to speak with influence, how to speak with impact or how to speak in a room full of people. We know what that looks like to buy. What I want to do is go, “I’m like those guys. I’m a little bit different. Here are three questions the person you’re going to go and ask for money from will probably ask you.” For consultants, have confidence in yourself to preempt the objection because you will either get to the no or the yes quicker. The thing we don’t like, it’s not the no, it’s not the yes, it’s the maybe. What you want to do, put as many unset objections up in the conversation and you move from maybe to no or you move from maybe to yes.

Prompt them with those things. One of the things I’m confident at because I’m a good listener, I will say, “You’re probably wondering why someone talking about listening is going to make a difference for your organization.” I’ll give them some stats like you’ll manage your spend 83% of their day listening and none of them have been trained how the cost of them not listening is you’ll lose great talent. They go to the competition. They’ll literally nod at you and go, “You’ve met some of our managers and you haven’t, it’s a generic problem.” What I will do is help those managers with that problem and then I’ll make an ROI case for it. We saved two of your high performers. You could pay for me for the next couple of years.

CSP 89 | Deep Listening


Do you ask them specifically what the salaries are of the two high performers? Do you get that granular around?

A high performer for you as a graduate is probably going to cost you $100,000 and high performing, high potential employee is probably at $250,000. If you lose them alone, the recruitment cost is $25,000. Think of me as your insurance policy against that.

Oscar, thank you for sharing some of these tips. There’s a lot here that is actionable for everyone. I appreciate you for delivering and offering this. There’s so much more that we could be getting into here. We’re going to look at this as the beginning and the start of more conversations to come. You’ve been now in the business for years building your own business. If you look at 2018 alone, what are you most proud of in terms of an accomplishment that you’ve achieved that others might benefit from learning about that they might be able to apply for themselves, real learning or some accomplishment?

If you’ll humor me with two, the first one is a quick one, the top twenty Apple podcasts in Australia in 2018 for my Deep Listening podcast series, that blew me out of the water. I was the only independent podcaster on the list. The rest were public broadcasters and big radio stations. Winning the award from Apple was something that was amazing. Somebody I mentored who’s one of the younger generations, took me out to lunch and gave me a plaque and said, “I notice you haven’t celebrated the fact you won this award.” They gave me a plaque and took a photo. I said, “Put that up on your social media.” I’ve done part one. I have to do part two. That’s what I’m proud of. The amazing thing about podcasting for consultants is it’s so much more shareable than any other content. I won a big speaking engagement with somebody who was in New Zealand listening to my podcast and sent a text message, SMS with a share of the podcast to a friend of theirs who was a CEO in Australia.

The podcast is such an intimate environment and potent to bring what you do as a consultant either through case studies and interviews or your own unpicking and to explain what you do. The second one is something completely unexpected. Patricia from the Netherlands reached out to me, had read my book and asked me if she could use it in her nursing training. All the work I do is basically based on a business environment. She said, “What do I need to do to license it?” I said, “You’re using it in the nursing field, take it. I haven’t got time for the legal on this. Go forth and do it.”

She sent me a copy of the training book that was used and it was a beautiful use of the five levels of listening. I asked her how it was being used. It was being used as they were screening a documentary in a Dutch hospital. It was nurses who had to listen to parents after they’ve watched this movie. I was super curious about what this movie was about. I said, “What’s the movie about?” They said, “Let me send you a link.” The trailer is in English, but the movie is only in Dutch. Unless you’re good at Dutch, you won’t understand this. The movie was called How to Listen to My Death Wish. I was completely blown away. I was shaking when I received this email.

It’s a documentary about adult children who have severe autism and realizing that their parents will pass away. Their parents have been raising them in their adult years. They can’t imagine life without their parents. If their parents were passing away in the Netherlands, euthanasia is legal as long as you have a doctor, a psychologist and a third person interviewing you and saying that’s your choice. I would never think that my work would be used in a context where people are choosing the ultimate decision about life or death. For all my work in the workplace, for all the employee engagement stuff, all the customer stuff, all of that pales into insignificance when I realized my stuff is being used in life and death decisions between parents, nurses and people with severe autism. That’s the thing I’m most proud of.

Oscar, thank you for sharing that with us. My final question here will be an easy one to answer. It’s the best place that you want people to go to learn more about you and your work.

I’ve got a simple download for your audience called The Five Myths of Listening and you can visit and that will give you the five myths as well as three tips on each to fix them as we’ve talked about with distraction. If you love listening to podcasts, I interview some of the best professional listeners in the world from judges to air traffic controllers to palliative care nurses on the award-winning Deep Listening podcast.

Oscar, thank you so much for coming on. This has been an enjoyable conversation.


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