Exploring the world of listening with Oscar Trimboli: Its importance, the 4 ‘villains of listening,’ and more

By Jim James, Founder EASTWEST PR and Host of The UnNoticed Entrepreneur. 

Oscar Trimboli is an expert in deep listening. In the latest episode of The UnNoticed Entrepreneur, he shared how listening impacts entrepreneurs.

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The Importance of Listening

Many of us haven’t been taught how to listen. Most people know Mathematics, wines, and cheese. However, there is no language around listening. 

Through his listening quiz, Oscar is trying to honour a conversation he had with a vice president, who once took him aside at the end of a meeting. The vice president told him back then, “If you could code the way you listen, you could change the world.” At that moment, it did not make sense to him because all he did was cheer knowing that he wasn’t fired (he initially thought that he’d get fired).

As a marketing director of Microsoft at the time, he eventually pondered on the question: Is it possible to code how people listen? Because it can be done for Math, English, or Chemistry. 

Afterwards, he set up an assessment tool that features 20 questions as a way of coding how to listen longer-term. Now, he’d also love to have automated tools or applications within Zoom, for example, that could tell one’s listening ratio. For instance, he imagines a percentage bar at the top of the screen. 

Screengrab from Oscar Trimboli’s website

Listening is crucial because the more senior you are in the organisation, the more listening you should do during your day. The more sales you do, the more your listening should also be. Unfortunately, this is not the case. 

When you’re dealing with complex collaborative, constrained, or conflicted situations, listening is one of the most important superpowers that you’ll have as an entrepreneur. Without that, you can’t bring people along in the journey with you. 

The difference between hearing and listening is the action you take. A lot of employees get frustrated with business owners to whom they keep telling the same thing yet get nothing. For business owners, listening is when you act on something you’re told about.

The Four Villains of Listening

Oscar and his team have done a lot of work with behavioural scientists, market research companies, computer software professionals, and academicians for two and a half years. The goal was not only to create a quiz but to prove it’s valid across English-speaking cultures. 

One important thing to know about listening is it’s situational, relational, and contextual. You’ll listen differently in many different situations. You’ll listen differently to a police officer than you will to a school principal, actor, or accountant.

According to their research, there are four villains of listening: the dramatic, the interrupting, the lost, and the shrewd.

Screengrab from Oscar Trimboli’s website
  • The Lost Listener. If you’re a lost listener, you would forget everything you’re listening to because you’re drifting off somewhere else. You might be thinking about something related to what you’re told about. The lost listener is completely lost in their devices or something in the conversation that triggers them to think about, for instance, a holiday that they wish they had. Of the 11,000 people who took their quiz so far, 22% belong to this category.
  • The Dramatic Listener. Dramatic listeners love listening to your story. They engage with you really well and often do too much of connecting with you. If you say to them that you’re struggling with a staff member, they’d say that you have to wait and listen to their problem about their staff member. Simply put, they love the spotlight being back on them. Though they love having a connection, they don’t understand the difference between empathy and sympathy.
  • The Interrupting Listener. The interrupting listening villain is the most overt listening villain. They’re the quiz show contestant who presses the buzzer, anticipates the question and the answer, but gets it wrong. They value time, and productivity matters to them. They have a mindset that they’ve already heard something before, so they tend to jump in and get to it quicker. While their intention isn’t wrong, they’re still considered impatient.
  • The Shrewd Listener. The shrewd listeners are problem-solving machines. Although they give you a great face and you feel like they’re really engaged in listening, in reality, this is what could be on their mind: I studied this long. I’m such an expert in this field and you’ve got such a basic problem. I’m going to think about three to six problems that you haven’t even thought about. However, speakers can sense this. They can see the cogs going on in these listeners’ wheels, turning over and going through the issues. Their mindset then is to stop these listeners from trying to fix those and get them to listen to what they’ve got to say.

The shrewd listener could also be thinking that they’re that kind of listener at work, but they’re a lost listener at home. When you take Oscar’s quiz, you’ll get a primary type of listening and a secondary one. The former is who you are at work; the latter, at home. 

He always points out that labels are good on food jars and pharmaceutical products, but not on people. That’s why during the episode, he reiterated that they’re not labeling you but your behaviour. 

On Self-Awareness

When it comes to listening, many people think that they’re above average. Oscar mentioned that around 74.9% consider themselves as well above average or a long way above average. And this shows an issue with self-awareness. 

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There are five levels of listening. The first level is knowing what your barriers are. 

Most people aren’t even aware of what gets in their way because when listening, they’re taught that the focus should be on the speaker. However, he’s not saying that you shouldn’t listen to the speaker; rather, you shouldn’t start there. You need to start by listening to yourself. 

Until you know your villains, you can’t introduce yourself to your superheroes. And for each listening villain, there’s an alternate superhero. If you take his quiz and sign up for the 90-day challenge (which can be found at the bottom of their five-page report), you’ll start to discover which one of those superheroes can emerge from you as you explore the world of listening.

A Little Neuroscience Hack

Oscar mentioned three numbers you need to know: 125, 400, and 900. 

On average, a person speaks at 125 words a minute (If you’re an auctioneer or a horse race caller, you can probably speak at 200 words per minute). Moreover, an individual can listen to up to 400 words a minute. These show that there’s a disconnect between the speed at which people listen and the speed at which they talk. 

Genetically and neurologically, you’ll get distracted. However, Oscar isn’t talking about mindfulness; he won’t teach you how not to get distracted. Because, ironically, if you’ll get distracted, it will help you reset your attention much quicker. Keep in mind that you can only listen continuously for 12 seconds. 

The number 900, on the other hand, refers to the number of words you can think of per minute. If you’re an entrepreneur talking to a customer, investor, or supplier, the other party is thinking of at least 900 words per minute. If you speak at 125 words per minute, it means that your listener is only listening to 11% of what you’re thinking about. 

The Three Questions You Need to Ask

You can get a fair advantage and get the next 125 words out if you learn three simple questions. And these will be significant in knowing your customer’s problems. As an entrepreneur, you can get a customer for life if you know your customer’s problems. 

The first question is: Tell me more. The second is: And what else? The latter, especially when saying “and,” should be done in a respectful way.

If you notice that your listener takes a breath in, their spine gets erect and their shoulders go back — that’s when you can use “actually” or “so.” This will help you talk about your proposition better (e.g. “Actually, now that I think about it a little longer, I think it’s more important that we talk about this.”)

The third question is the shortest yet the most powerful: silence. If done poorly, however, it can intimidate. 

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In Mandarin, “ting” means “to listen.” If it’s not pronounced correctly, it can mean “to stop.” When it comes to China, listening is six-dimensional. It’s about seeing, sensing, feeling, respecting, being present, and being focused. This is what “ting” means.

One of the critical skills that the East teaches us is silence. If you can practice that, you can hear things that other people will never get told about. And it’s because you took the time to listen to something that’s not said. With it, you can uncover things much more than the next person — who merely engages in a dialogue — can.

In the West, there’s this thing called pregnant pause, or the awkward, deafening silence. In the East, this is viewed as a sign of wisdom, respect, seniority, and authority. It’s not uncommon for there to be long pauses. 

Silence needs to be skillfully used because it can be intimidating. It needs to be skillfully done especially when you’re in some kind of a relationship and trust is being developed.

Most of Oscar’s clients, particularly those who are entrepreneurs, often say that they don’t have the time for all the listening stuff. However, he counters it by saying that it also takes up time if you launch the wrong product, or if you lose a great staff member. All these are unprofitable ways to spend the day and make use of your time and money.

Although listening takes a bit longer especially during the beginning, what you can do is to start to listen to what speakers are thinking and what they mean, rather than merely listening to what they say. If you’re an entrepreneur and you listen to what your customer, investor, supplier, or employee says and what they mean, you’ll have them for life.

On Being an Entrepreneur Himself

When asked about the entrepreneurial aspects of business, Oscar discussed his failures first.

Image from Oscar Trimboli’s website

For example, when he was attending an industry conference about seven and a half years ago, sitting next to him was someone named Dermot who was originally from Ireland (He eventually became his good friend). During a workshop, they were asked to share a problem that they’re working on. Back then, he had been blogging for two and a half years straight on the topic of listening and nobody was engaging with what he was doing. What Dermot said is, “If you’re talking about listening, you do a podcast. You don’t blog.” 

He realised that if people are interested in listening, then they’d probably want to listen to it. 

He then started one, which was another “spectacular failure” — until he discovered a wonderful book called “Selfish, Scared, and Stupid” by Dan Gregory and Kieran Flanagan. They hypothesised that you can do all the ambitious, inspirational, and aspirational work you want. But take note that most people relate to their weaknesses more rather than their strengths. Thus, his creation of the villains of listening.

Initially, he thought about talking about aspirational listening superheroes. But nobody could relate to them because they’re artificial gods of listening. On the contrary, he hasn’t met yet a single person who can’t relate to his four villains of listening. 

Oscar also considers publishing as a thing he does well. However, it doesn’t simply mean publishing a book. It also encompasses sharing ideas with somebody else. 

In this aspect, publishing can mean doing webinars. In his practice, he also runs a community where people in his newsletter lists can attend webinars once a month for free. He also uses this as a way to test ideas and get feedback. 

Additionally, these people also share with him contemporary problems that they’re dealing with in their workplaces. If he’d listen carefully, he’d be given a lot of great opportunities to think about. 

One of the things that emerged from that is the deep listening playing cards. When people asked, “Why don’t you put all those tips you talk about into a set of playing cards?” He did as such. When the idea of making a jigsaw puzzle was brought upon, he and his team also made a jigsaw puzzle. The same with the assessment quiz and his book

Image from Oscar Trimboli’s website

Another thing that he’d done well is the podcast. A few years ago, it won an award from Apple for the category that it’s in. The podcast offers a different take on the communication topic. It talks about listening and features interviews with expert listeners to deconstruct what good listening is and how to make that commercial. Now, a lot of his clients came from those interviews that he’d done two to fours years ago. These are people who heard and continued to follow him. 

Publishing, for him, is also about going through that process of speaking to people out loud. It’s important because someone can eventually connect with what you’re saying. 

In the old days, Oscar used to speak at public events. Now, even up until midnight to 2 o’clock in the East Coast in the US, he has sessions. He also has evening sessions in Hamburg, Munich, London, and even Copenhagen. Amidst the pandemic, so many opportunities have come about, extending his work around the world. 

While he made a lot of mistakes, Oscar stressed out that it’s through them that he got ideas and feedback. For him, the key to his success is persistence and some kind of plan.

Online Tool for Listening Scoring

Oscar and his team work with a third-party software organisation called Evaluation Solutions, which does assessment tools for people around the world. The tool was integrated into their CRM system (in their case, it’s Infusionsoft). 

Through the quiz, they get rich information about people who take the quiz. Then they connect them to a 90-day challenge. 

About a third of the initial quiz responders opt-in for the challenge, and 20% of those people complete all 13 weeks. And from these 13 weeks, they get to notice behavioural patterns (e.g. Which newsletter copy do people connect with and not?), which they then apply. This is why the challenge that they offer is different now than how it was a few years ago. 

To learn more about Oscar, the listening man, visit https://www.oscartrimboli.com.  

This article is based on a transcript from my podcast The UnNoticed Entrepreneur, you can listen here.

Cover image by Christina @ wocintechchat.com on Unsplash.