The most comprehensive listening book
Apple Award Winning Podcast
Podcast Episode 057: The Five Levels of Listening – Listening for the Context

Subscribe to the podcast

Listening for the context is Level Three listening.

Context is all about the backstory. It can be the difference between a productive conversation and a frustrating, circular discussion that goes nowhere.

Deep Listening is three dimensional: your context, their context and the context of the conversation.

In this episode, learn the cost of ignoring context, and how it cost a quarter of a million lives in July 1945. Hear stories about the difference that listening for context makes in the office.

Learn from Oscar and Nell how to unlock the context and take the next step on your journey to becoming a Deep Listening.


Episode 57: The Five Levels of Listening – Listening for the Context


There’s a pattern to the speakers, which is to prepare you for what they’re about to say. They’ll say the thing and then they’ll repeat it.


A lot of it is really tuning in to the adjectives that somebody is using. The adjectives are almost like road signs in terms of which direction the person is coming from or which direction the person is attempting to go to. By listening to those repeatedly, you can get a sense of the world view.


She’s studied them, and she’s listened to them. One of the things I learned from her was how to listen for capital letters. By that, I mean, she listens for those points of inflexion or points of emphasis, where if you could visualise it in your mind, they would be saying them with capital letters. So listening for those capital letters to say, that’s it. That’s what they really mean to say, or that’s important to them. I’m going to write that in capital letters because that sounds like it’s a big deal.

Oscar Trimboli:

Deep Listening, impact beyond words. I’m Oscar Trimboli, and this is the Apple award-winning podcast, Deep Listening, designed to move you from an unconscious and distracted listener to a deep and impactful listener. Did you know you spent 55% of your day listening, yet only 2% of us have had any training in how to listen? Frustration, misunderstanding, wasted time and opportunity, along with creating poor relationships are just some of the costs of not listening.

Each episode of the series is designed to provide you with practical, actionable and impactful tips to move you through the five levels of listening. I invite you to visit to learn more about the five levels of listening, and how to learn from others who are listening better. Joining me is our co-host, Nell Norman-Nott, who will ask the questions that you’ve been asking and asking me the questions I haven’t considered, to help make you a deep and impactful listener.

Welcome to level three, listening for the context. Today, we’ll provide you with the recipe to understand what it means to listen to your context, to listen to their context, and to listen to the context of the conversation.

Context is all about the backstory. It’s what comes immediately before and after a particular phrase, or a story that makes up part of the conversation. It’s about a framework. It’s a scaffold that keeps the conversation together in your mind as the listener, in the mind of the speaker as you and them progress the dialogue.

Context has many influences. It has influences from past events, the current situation you’re in, and possibly what’s to happen in the future. If you think about context as a word, its origin meanings, the Latin origins of the word gives you great context, because it’s made up of two parts. The first, the Latin word Con, means put together or to weave. So weaving together the dialogue is the linguistic origin of the word context. When we weave together all three parts of the recipe; your context, their context and the context of the conversation, it’s really important to understand that context is three dimensional.

Context is about patterns and language, especially understanding the backstory. So, today, Nell and I are going to provide you with some tips, some tricks, some techniques, and some questions to help you see the context in every conversation and use it productively.

You see, context spans cultures, teams, organisations, countries, languages. It spans how you deal with time, whether you speak about things as an individual, or whether you speak about things as a collective, as a team or an organisation. It’s when you unlock the context, that’s the difference between a really frustrating and circular conversation that seems to go nowhere. It’s like being stuck in a holding pattern in a plane circling around the airport, waiting for your turn in the conversation.

Your conversation without context, it’s just stuck. You’re not clear about the context, and the cost of not listening to the context is huge. It typically results in frustration, not only for you, but equally for the speaker as well. Now, thinking about context, what does it mean for you when context isn’t there?

Nell Norman-Nott:

What you said, Oscar, about knowing the backstory really resonates with me. Because I had an experience where I been off on maternity leave with my daughter. This was about, gosh, maybe about five years ago now. I’ve been at LinkedIn prior to going on maternity leave for four years. I knew the company really well. I knew it inside out. I’d seen it grow from a little office of 10 people in Sydney on Pit Street, bigger premises that we’re all singing or dancing and stand up desks and everything.

Then I went off, 12 months, great time with my daughter. I was super excited to come back to work because it was a great team there. I felt comfortable, it was a place where I really felt at home. The thing that stood out to me was I got straight back in, I was going to meetings and I was getting involved in projects and just felt like something was missing. Because I’d had the last 12 months off when obviously everybody else had had these conversations and meetings about projects and things had happened, things have changed at a global level. They bought in new systems, new processes that I just wasn’t familiar with.

I can see from an external outsider’s point of view from other people that were seeing the situation I was in, they didn’t know what I didn’t know, and I didn’t know what I didn’t know. I literally didn’t have that backstory of what had happened over the last 12 months.

I thought about it and I do quite like thinking about things visually. For me, I had this giant jigsaw puzzle, and I was trying to put things into place and trying to find the pieces. But there were all these gaps all over the place. I’m sitting in conversations thinking, I have no idea what you’re talking about.

When you say to me, what is context mean to me, that is an experience which shows me how much not having the context can make a big difference.

Oscar Trimboli:

When you’re coming back, you’re probably familiar with the people and your loss, what did you do? How did you come up to speed on the context, or did you just move through the conversation guessing? What happened?

Nell Norman-Nott:

It depended a lot on the context. Sometimes I would just sit there and take a lot of notes and go and speak to somebody quietly about it afterwards. But what I typically try to do because a lot of those meetings started off with your usual office chit chat and “Hey, welcome back, Nell, how was maternity leave? How’s it being back at work? Are you enjoying it?” As part of those conversations at the beginning, I tended to say, “Well, it’s great to be back. I’m loving being back.”

What it feels like he’s I’ve got this giant jigsaw puzzle, and I’m trying to piece it all together because there’s a whole load of things I don’t know that I missed out on. In that way, I subtly hope to set the scene that if I asked some pretty stupid simple questions that everyone else in the room knew about then that was why, that was where I was coming from.

Oscar Trimboli:

Working with a number of employers of choice, organisations that have won awards for the way they help people out in transitioning back from maternity leave, one of the things they all do really well is they invite the person who’s on maternity leave into the team meetings at least once a month. Now, it’s up to them about whether they turn up.

I can guarantee you, everyone would love to see the baby. So, that has never been an issue with the clients I’ve talked to, yet it keeps you in the context, it keeps you dancing across the top, that gives you a template for this jigsaw puzzle that you’re trying to piece together in your head.

For those of you out there who are leaders working with people who are away at maternity leave, don’t leave them in that big gap. Don’t throw the jigsaw puzzle pieces on the table, the day they get back, you can definitely set up the context well in advance.

Nell Norman-Nott:

Also, any type of leave. Go away for a couple of weeks. Any type of scenarios is potentially, I think progressively we’re getting more flexible as organisations to allow people to have time out. There’s going to maybe be more moments where people do have that kind of experience.

Oscar Trimboli:

There are some cases where the context makes a huge difference. Contexts can cost people’s lives. Context can cost a quarter of a million lives. In July, 1945, Allied translators misinterpreted the Japanese Prime Minister’s use of the word mokusatsu at the start of a press conference. You see, Japanese is a highly contextual language. You see, the word could mean many things depending on the context. The word could mean on one hand, it could mean ignore everything that has been said or take no notice of it. But this word could also mean treat with silence or contempt. That might be its classical meaning.

But in this context, when the Japanese Prime Minister was being interviewed by a journalist to understand how he would respond to the Allied terms of surrender, it could have been interpreted as the comment he made no comment, which is typically the context of how a politician would respond to a journalist question. But in making the translation from Japanese into English, the translation was made completely out of context. It was done word by word. If we listen to our previous translators, whether it’s Christina or Eva, they all talk about the fact that all translation needs to be in context.

What the Allied commanders received, the Americans, the Russians and the English, they were told the Japanese Prime Minister is completely ignoring the terms of surrender. As a result, the Allied leaders decided that they would bomb first Hiroshima and then Nagasaki.

Unfortunately, the cost of not listening to the context, and the context of the word mokusatsu, this cost a quarter of a million lives, a quarter of a million lives lost in Hiroshima and Nagasaki less than a month later in August 1945 because the translators didn’t take the time to fully understand the context of the simple word, mokusatsu and what it could mean. Like most words, mokusatsu had a multiple meaning. In this case, the multiple meaning had dire consequences. the consequences of not listening to the context can be pretty horrific.

I was speaking to somebody a couple of weeks ago, and they just said, “I finally understand what you mean when you talk about listening in Technicolour, Oscar.” Because we were going through context with them. I think for a lot of us, we come to the conversation, completely scaling across the top of the context. I think a lot of context has to do with the backstory and the history that both of you bring to the conversation. And it’s a lot to do with assumptions.

Nell Norman-Nott:

You talked about listening in Technicolour. Can you give us the context around what you mean by that?

Oscar Trimboli:

The context was, I was running a training course and my opening line is all of us see in colour, but we listen in black and white. Most of us only listen in two dimensions. We listen for what we see, or we hear. But there’s only really two dimensions of that. We’ve already gone just on level three and listening for the context. There’s another three dimensions there. If it was a mathematical formula, not that I’m good at them, but there would be context to the power of, is it cubed? What’s after squared? Was it cubed? To the power of three?

I want to make sure that all of us are conscious of our mental models, and we have a way to use context as scaffolds and frameworks to bring the conversation to more effective place. That context is a lot about the relationship. We spend some time talking about that, particularly with that email example. But ultimately, and more importantly, it’s the context of the conversation. It’s the actual dialogue itself that we need to be conscious of.

Because a conversation is created at a point in time, it’s really unique. It’s in this case, it’s three dimensional, and it’s the only thing that unifies you as the listener and me as the speaker. So, it’s unique at a point in time. Circumstances and the point in time, that means that we have to listen differently today than before we went on maternity leave as an example. I always say, dialogue is like a living organism. It exists at a point of time. It only exists for a fraction of a second.

Without the context now, the opportunity for misunderstanding is huge. It’s huge because it’s a simultaneous equation you and I are talking. You’re listening, I’m speaking I’m listening to you, you’re speaking back. That’s only going to exist at a point of time. I think of it like a dance that you need to maintain some level of balance. You have to understand who’s leading, you have to understand who’s following and that might change because the music might change, the context of the conversation might change.

Now, let’s think about the context as being bound by a series of assumptions. Some you may be conscious about, some are explicit, some are declared. Usually though, most people aren’t even aware of the assumptions, they’re not aware of the assumptions that they have. They’re not even aware of the assumptions the speaker has. It’s really critical for all of us to notice our assumptions. If there’s one thing you want to take out of this episode, is context is the backstory. Without the backstory, the foundation of the dialogue is completely undermined.

Context is what happens immediately before and after a particular phrase or a set of dialogue that you’re discussing. This way of thinking helps us all create something that has a beginning, a middle and an end. You see, the context is influenced by historical events, from way back in the past. It could be how they grew up with their parents, it could be where they’re born, it could be the language they learned at school. But the past might also be the immediate past. The last conversation they had or the last meeting they had.

Your context is your mental framework. Context has three elements; your context, their context and the context of the conversation. What you bring to the conversation is just as important as what they bring to the conversation. It could be a set of experiences on this particular topic, or it could be about lack of experience on this particular topic as well. Your context is unique to you, as their context is unique to them. But as we put those two things together, we get a really unique circumstance whenever we bring a group of people together. Whether that’s two people in a dialogue, or a team meeting in a dialogue.

Unfortunately, though, for most of us, the assumptions that underpin our context aren’t even conscious to us. We don’t even realise them. Some of them are so subconscious that they come at a cost.

Now, one way to think about context is always to think about it as the backstory. If you can think about, do I know all the backstory here? Sometimes context is like walking into a living room where somebody’s been watching a movie and they’re halfway through it. You sit down, you try and place the characters together, but it’s not quite the same experiences if you start the movie at the beginning. Let’s jump into a movie that’s halfway through.

An 18 year old contestant is on a TV Quiz Show. He seems really smart. He seems really clever. In fact, too clever. He answers most questions without a pause, with no misstep. As a result, he’s currently being investigated by the police.

Now, this could be many movies now. But let me describe exactly the same movie with a bit more backstory. Jamal was an orphan. His mother was killed in a street riot when he was five years old. For the next 13 years, Jamal and his older brother Salim live on the streets in Mumbai until they’re kidnapped by a gangster who uses children to pickpocket and beg for money. Jamal navigates his way through the slums and ultimately is employed in Mumbai in a contact centre, where he’s trying to learn all kinds of trivia about TV shows in the West, which makes him an ideal contestant for a TV Quiz Show.

The backstory about Jamal, the slums, it all creates contrast, tension, and an understanding for the movie. But without this, Slumdog Millionaire could just be a show about a smart guy who’s been arrested because he’s gaming the quiz show. But for most of us, what we do is we say, smart guy answering all the questions, being investigated by the police, it only took me 30 seconds longer now to tell the full story about Jamal. Now, I know Slumdog Millionaire is by far one of your favourite all time movies.

Nell Norman-Nott:

Yeah, I can guess that movie from your first iteration of the storyline, which helps make that point that if you were in that meeting room and you start a topic, there may be some people in the room that immediately get what you’re saying. But as you so eloquently put it, when you explain more of it, that just means that everybody in the room understands the context at which you’re discussing that topic.

Oscar Trimboli:

So, no time is wasted when you invest spending a little bit more time talking about the backstory. In fact, one of the deep listening playing cards helps you to signpost some practical ways to think about the context. One of the cards asked you, in fact, it implores you to seek greater dialogue clarity by noticing patterns in the conversation. It encourages the speaker to seek examples and stories rather than just facts and figures.

If you’d love to get your hands on those cards, and know lots of you have been enjoying using the cards, we’re going to include some feedback about the cards on future episodes, you can visit, and I invite you to grab the deep listening playing cards there.

One of the clients that I work with actually uses this context card specifically in sales meetings every month, and they use that card to bring to life what is missing in the customer’s backstory that they’re trying to sell into. The room actually now splits into two. One half of the room plays the customer, the other plays the organisation, they swap roles, but they ask questions about the context and the backstory. They ask questions about who else is affected if this was to be a project, who else besides these people would be affected?

All of a sudden they unpick really quickly a lot of context they haven’t asked. Initially they said it felt clunky but it’s now part of their operating model. A new person came along and sales leader opened the box of playing cards, and I thought that would joining a cult because it looked like a little Bible that they were about to read.

Nell Norman-Nott:

Like the Tarot cards.

Oscar Trimboli:

Maybe it was Tarot cards too.

Nell Norman-Nott:

I’m curious though, Oscar, because I think so often you can be in those situations with a customer. You have the set questions that you would ask; what are your challenges that you face? What are your plans as an organisation?

How do you come up … I think you get in a routine of asking set questions, how do you break that habit? How do you think of, practically, what are the things that you can be doing in those scenarios?

Oscar Trimboli:

About four weeks ago, I was asked, What’s the difference between distracted listening and deep listening? It comes to the question you ask, if you’re asking those questions, your orientation is to help make sense of it yourself.

The questions you need to ask in those situations are not for you. In fact, that’s why the questions come across as mechanical. Deep listeners help the speaker make sense of what they’re saying, not themselves. That’s why deep listening is easy, why it’s live, and why it’s impactful. The kinds of questions you need to ask at that point now, aren’t these mechanical ones. Quite often, they’re scripted. Sales people are lawyers, accountants, people who are in advertising agencies, anybody who takes a brief, a doctor, a physiotherapist, a dentist, all these people have a script in their head, which means that orientation is on themselves, rather than thinking about the collective.

It’s not about your orientation being exclusively on the speaker. How do we make sense of this conversation, but particularly for them in that moment, where you’re struggling with, what’s the question I should be asking at this point? Sometimes the most potent question is to simply say, what else? Tell me more. Do that in a way that helps them understand the past of this much more, rather than the future of this.

In the brief taking professions, in the sales professions, all those organisational context you talked about there, Nell, most of those questions are going to be orientated to the future.

Nell Norman-Nott:

I just had something click in my head because I know what you’ve been doing now, Oscar. Because when you and I meet, at the end of every conversation, you say, “So, what haven’t we talked about? What’s the thing that we haven’t covered up in our conversation?” It gets me thinking differently, because it’s kind of an awkward question. It’s not typically part of whatever we’ve been discussing. I just say it works. It’s definitely something that I look to use that more.

Oscar Trimboli:

When we think about that question, and not that everybody had a chance to see you say, something’s just clicked for me, but when Nell said it, her eyes were in a completely different position. Her spine came into a very erect position, her shoulders went back.

When we talked about listening for content and we said, how do you sense where the energy is coming from, Nell’s energy is in a completely different state now? I’m glad that listening to the context has helped unlock some stuff for you, and equally for me.

Look, context is a framework for you. It’s a way for the listener to explore their own dialogue. It helps you and me, Nell, to understand the assumptions, the assumptions that sit there. Some of these assumptions are productive, some of these assumptions are unproductive. The story for me that brings this to life is an expat leader that I was working with a couple of years ago, he was on a three year international assignment. He’d moved from Europe to Australia, and he was exceptional, and he led a team of about 45 people. He was in the telecommunication sector, and he was a leader I admired. He had great relationships with all of his employees, but there was something that [inaudible 00:26:00] Andy. It was something about 12 months into his assignment that didn’t quite sit right for him.

Now, Nell, the context and the backstory for this is Andy told this story immediately before I worked with his team for half a day around deep listening. Imagine you’re getting told this story for the first time and I had to experience this story for the first time. He said to me, “There’s one person in my organisation who always is part of the birthday celebrations. She’s the person, Kim, who was always handing out the birthday card and organising the cake and leading the happy birthdays.” But after 12 months, Andy was super frustrated because he didn’t know when Kim’s birthday was. He felt there was some trust barrier there.

What he did was really interesting. In his next one on one in a private setting, he sat down with Kim and basically said to her, “Look, is there a trust issue between us? Because you’re engaged so well with everybody’s birthdays, you’re getting the card signed, you’re baking cakes. You love birthdays for everyone but none of us know when your birthday is on.”

What he said next really touched me. What he said next was, “Kim, is there a trust issue between us?” Kim just looked at him and with a very, very faint tear coming down her cheek, she said, “Andy, the reason I don’t celebrate my birthday is my mom died giving birth to me.” Andy was blown away because he’d obviously made lots of assumptions. He paused and he just looked at Kim. Kim said, “My birthday is the 18th of February. I trust you with that information. You can choose to do with it what you wish. But now you know why I don’t celebrate my birthday.”

I think in the workplace, there’s lots of those assumptions that fly around. I was only talking to somebody the other day saying in Nepal, they don’t celebrate birthdays. They were quite shocked. As a nation, as a culture, they don’t celebrate birthdays. The point is, Andy took the time to learn the backstory. That’s the point of the story. Instead of having a fractious, friction filled relationship with Kim, he had a completely different one. In fact, a relationship with so much trust that he tells that story in front of 45 people before I turn up.

Now, Kim was literally sitting in front of me, and she was composed and obviously they’d agreed that it was okay for Andy to tell that story. But for a lot of us, we’re missing the point of birthdays in every conversation. Our context is very different to the context of the other people in that conversation.

Nell Norman-Nott:

It’s so relatable, that story with so many organisations now having global footprints. When you think about like you were saying in Nepal, they don’t celebrate birthdays, there must be a lot of listeners who experience similar things with colleagues that are overseas or friends who are from overseas. I had an experience when I very first started working at LinkedIn. I was due to fly out to Hong Kong. We were colleagues who were Chinese and who were from Hong Kong. There were also people flying from other parts of the world.

We suddenly got an email saying, actually, this is cancelled, because someone has scheduled this meeting and it’s right over Chinese New Year. They’ve had no idea that this was such an important event. In my own mind, I was like, oh, yeah, Chinese New Year where you get the little red packets out. But of course, for me, it would be like, I celebrate Christmas. It will be like holding this event on Christmas Day. That was something I hadn’t thought about, and the person who’d organised that meeting hadn’t thought about.

There must be so many examples of those sort of situations happening all the time, we don’t bother to really understand the context.

Oscar Trimboli:

It’s true. I think, spending a little bit of time at level three with a Deep Listening playing cards and exploring some of those questions would be a great starting point for anybody to talk about this.

Nell Norman-Nott:

We’ve got a great question from Charity about context.


Hey, Oscar, love the first episode of the new series. I’m just wondering, what happens if you do come in halfway through the movie, if you haven’t been listening properly, or you haven’t set the context that you’ve got a long standing relationship? How do you set the context from halfway through?

Oscar Trimboli:

Thanks, Charity. Great question. I think this the moment that we need to be honest in our communication. I think honesty in communication is so liberating. I’d say, the simplest thing you can do is be honest and say, “I’d love to know a little bit more about this topic. Could you just go back a little bit further because I sense there’s part of this backstory I’m missing.”

I think if you signal backstory in your language, that allows the speaker to take it as far back as they think necessary. If you’re still stuck, Charity, and they haven’t gone far enough back when they do, just say, “Could you go back a little bit further into that story?” Where did it start from would be a great code word to use? Where did it start from? When did this project start? When did this issue arise?” Is a great way to explore that.

But I think honestly, at this point in the conversation, and Nell, I know you have a giggle, but I probably spend more time saying, “Sorry, I got distracted. Could you say that again, please?” People are just refreshing Lee surprised by my honesty, but attracts great improvement in the relationship, because they know I’m not faking it, I really want to listen.

So, Charity, just be honest and say, “Can you take me back to the beginning of this story.” Let the speaker guide. If they don’t go back far enough, then you can explore a little bit further again. Thanks for a great question.

Nell Norman-Nott:

Hey, Oscar, I’ve got a question as well. You work with people every day with executives and leaders, you run presentations and keynotes the whole time. When people come to you and ask you for help in listening to the context, what do you advise them, in addition to what you’ve just told, Charity.

Oscar Trimboli:

Talk me through where this became an issue, or talk me through where this started, or what’s brought us here today. That’s one I use a lot. Thanks for inviting me to the meeting. Inside your organisation, what brought us here today. A lot of the time, someone will lead that part of it. Then I’ll take an external orientation and I will say, for me to make this really effective for the audience, what else in the backstory do I need to know, because they’ve lived the backstory.

All of a sudden, other people in the room are engaging differently in the conversation because they have a different perspective. I think in your consciousness to be going, who am I here for in this moment? Because quite often, we’re not here for our own progress, our own learning, particularly when it comes to the keynotes. People comment to me. I’ll always ask, what happens immediately before I get on stage? But I also ask, this time last year, when you had a similar presentation, what happened, and what happened in between?

They’re filling in their own backstory. What’s happening in that moment, I’ll explore with them to go, how did you sustain that change that that speaker spoke about? I could remember one recently where they just went, “Wow, we didn’t even think about that.” I said, listening is a practise that we want to able to sustain change. For me, it’s what happens immediately before I step on stage. Equally, who’s coming after me? When are the breaks? Did they have a party the night before? Because they could be turning up hung over, particularly in Australia.

Nell Norman-Nott:

I feel like that is great advice for anyone who is listening that’s planning their next corporate event. It’s something I wish I knew all that when I’ve been planning events in the past because I would consider that agenda very differently knowing what you’ve just said now.

Oscar Trimboli:

For a lot of the people I work with, Nell, they realise that in that moment, I’m role modelling deep listening. In fact, I can remember Michael couple of years ago was doing an event out of Manly, a beautiful part of Sydney for those of you who haven’t been here. If you had to come to Sydney and you want to go to Bondi, make a point of also going to Manly. They’re both beautiful beaches in different ways.

He said to me at the end of his brief to me, he said, “But I’ve already learned so much from you about listening just by watching you in action.” I think that’s the tension I work with every day, Nell, is how do I be deep listening rather than do deep listening? Because it becomes a little bit easier for me. That’s how I bring context to life when I’m taking the brief.

Nell Norman-Nott:

Thanks for sharing that. I feel like that is a little glimmer of an insight into Oscar’s brain and the way that you think, which is probably a pretty amazing place to be, aren’t we?

Oscar Trimboli:

Now, context is also listening for patterns. It’s listening for patterns in language. I had the opportunity to listen to world-class listeners, Sarah Manly, Michael Henderson, and Anthony [inaudible 00:35:47] Sarah from Episode Three, Michael from Episode Five and Anthony, from Episode 18, spectacular examples of listening to what’s repeated, noticing how adjectives use consistently to create context and also listening for the capital letters in the conversation to notice the patterns that the speaker is using. Because we want them to become conscious of what they’re doing. For a lot of us, we speak in patterns.

Be curious if anybody noticed the kinds of patents that I speak in. Let’s listen first to Sarah, then to Michael. And finally Anthony.


There’s a pattern to the speakers, which is to prepare you for what they’re about to say. They’ll say the thing and then they’ll repeat it.


A lot of it is really tuning into the adjectives that somebody is using. The adjectives are almost like road signs in terms of which direction the person is coming from, or which direction the person is attempting to go to. By listening to those repeatedly, you can get a sense of the world view.


She’s studied them, she’s listened to them. One of the things I learned from her was how to listen for capital letters. By that, I mean, she listens for those points of inflexion or points of emphasis, where if you could visualise it in your mind, they would be saying them with capital letters. Listening for those capital letters to say, that’s it. That’s what they really mean to say, or that’s important to them. I’m going to write that in capital letters because that sounds like it’s a big deal.

Oscar Trimboli:

I’m wondering if you’ve noticed any patterns in the way I speak during this episode, or looking back at past episodes, and the way I speak? Are there any patterns you notice in the way I pose questions to the people I’m interviewing? Do you notice any patterns in the style of questions I use or any patterns in how I use silence for example? That all creates the context.

One of the things I do deliberately is used pause. I always try to help the speaker explore and reflect about what they’ve said. More importantly, to explore what they haven’t said. If we remember the 125, 400 rule, as well as the 125, 900 rule, it applies equally for the speaker as well as the listener. I have 900 words in my head right now that’s really frustrating because I’d love to get them all out. But I can only say about 125 words a minute.

For Nell, listening to this, I know it’s frustrating for her too. Whether it’s Nell, or Jenny, my wife, Lauren, my step daughter, they always say, “Oscar, why do I start your sentences halfway through your thoughts? We always feel like we have to catch up. Nell, are there any patterns you notice in the way I speak?

Nell Norman-Nott:

When you first told me that as people we think at 900 words a minute. I sat there thinking, Oscar, you probably have more than 900 words that came through your head. Because when we first started working together, yeah, I would agree with Jenny, your wife that you did just start talking about topics and I would have to very quickly try and think, what’s he relating to? Where are we going to now? Are we are we talking about this event? Are we talking about this customer? Are we talking about the podcast? Because you would bounce from one thing to the other. They think you were relaxed in that scenario, and in all of the information was just there and it was coming out.

I also noticed when you’re very deliberate and thoughtful in the way that you’re speaking as well, such as you exhibit on the podcast. One of the things I know I struggled with was how I interrupted you in those thoughts and what kind of questions I would use to get the information that I needed. Which is something personally I’ve struggled with. For years, I thought I’m not good at asking questions. I just don’t know what to ask. I feel like I want more information, but I don’t know how to elicit that information.

One thing that stood out to me is that I asked a lot of why questions. Why questions are easy questions? Why are you saying that to me? Why do we need to do that? When I listened to Episode Two that you recorded with Alan Stokes, it was like a light bulb went off my head. I realised that Alan says why questions are loaded with judgement . I thought, that’s why people don’t like it when I asked why questions, because it feels like I’m judging them. I’m not, I just want to get the information out of them.

You’ve taught me, working with you and understanding more and more about deep listening and going on this listening journey myself, that for me, I need to consider more the types of questions I ask, and how I’ll ask them, and when you or anybody else that I’m talking to, Oscar, comes to me halfway through the backstory. They don’t offer that backstory. I need to think carefully about how I structure those questions, and would use things like I’m curious, and I wonder and what, and how questions, which Alan talks about so beautifully in that episode.

Oscar Trimboli:

Always remember this, most of the time you got asked a why question from your parents the first time is when you did something wrong. Why did you do that thing? It may be something that you say a little bit more often than you want to at the moment. I’m on [inaudible 00:41:39] that her part of the brain that’s connected most to the fight or flight mode when we hear why questions, we’re propelled straight back into the judgement of our parents in that moment when they ask why did you spill the milk or why haven’t you cleaned your room? All of us just need to be conscious of too many why questions. Particularly at the front of the conversation. Towards the end, after you’ve had the dialogue, that probably works.

You raise a good point. And Alan makes it beautifully. We’re going to spend a lot more time with Alan, in the next episode where we go and explore what’s on said. Pattern matching and pattern noticing is the most important things we actually do as humans. It’s one of our survival instincts. Sometimes we notice patterns too quickly, Nell, and sometimes we don’t notice patterns at all. Patterns are coded into our assumptions and our assumptions are put there so we can get through life faster. We don’t want to question the assumption that there’s gravity on the earth every day, the minute we step out of bed, we’ve just got to assume that it exists. So that’s an example of a really good assumption. But in a lot of dialogue, and in a lot of discussion, sometimes we need to surface assumptions, and that’s really important.

One question, Nell, that I find really powerful to explore patterns and context is simply by asking the speaker, what patterns have you noticed in our conversation so far? That’s not designed for me. Because I in my head, I might speculate what patterns exist. I can guarantee it, Nell, every time I ask the question, the patterns they come up with completely different. The potency of that is, it’s they’re noticing. If they do the noticing, it’s more powerful for them, particularly if you’re trying to help somebody to make a change.

One of the things I’d often ask organisations that I work with is, what are the habitual things, what are the rituals that this organisation does, because that’s an example of organisational patterns as well. What that helps them to do is shine a light on what are the productive ones and what may not be the productive ones as well.

A lot of the time, typically, we find that the patterns are all about internal orientation rather than being externally orientated on customers or competitors or regulators in their marketplace. Nell, sometimes you have to think about when you do point out, or notice these patterns, sometimes it’s helpful for them, sometimes it may not. Sometimes you might want to just make a point. Sometimes the most powerful thing you can say, and it’s covered off in the playing cards, and it’s the final question I love to explore, which is also on the deep listening card. So, check them out at

The question this card poses is, what’s the most productive way we could conclude this discussion? Sometimes, people want to go deeper into the dialogue. Sometimes they want to skate across the top rather than going into more detail. More context and more information can be useful for them as well. The trouble, Nell, with that question is most people ask it with five minutes to go, where they need to ask it for one hour meeting, at the 30 minute mark, or the 40 minute mark, or the 45 minute mark, where you can actually do something with that information.

Nell, I loved the reference to the jigsaw puzzle during your maternity leave story, as you came back, jigsaw puzzles fascinate me and jigsaw puzzles are part of the method we use when we’re bringing people listening to life.

Nell Norman-Nott:

They’re literally part of the method, you use, Oscar, because we’ve ran the event together in May, back at the Hilton in Sydney, and this was a workshop. I noticed that the tasks that people had to do was put together a jigsaw puzzle, which has an obvious great analogy. Also noticed through that scenario of executing the event together and planning it all and putting everything in place, if anyone knows running an event is lots of things to think about.

Oscar Trimboli:

But let’s be honest, Nell, we had a [inaudible 00:45:45] when we were setting up this event.

Nell Norman-Nott:

There was a bit of a point of contention, Oscar. I totally agree. As people were doing the jigsaw puzzle exercise, I said, what’s going to be going on, what’s the atmosphere that we’re going to be creating? Because when you create … I’ve done hundreds of events. You think about that experience, that experience of the individual from the start to finish and what’s the atmosphere like in the room? What’s it like when they go out to break?

I said to you, while people are sat down at the tables, and they’re putting this jigsaw puzzle together, let’s put some music on, we need some atmosphere in the room because we need to take them on this kind of journey. You said, no.

Oscar Trimboli:

I said, no, forceful.

Nell Norman-Nott:

You said, no. I could tell from the pattern in your voice, you meant it. It wasn’t until I was in the room that I understood why. It was around creating that atmosphere that was right for what you were doing was actually silence was the best thing to have at that time. You talk about using the pause and sometimes silence is just the best thing to create the environment, the atmosphere that you need. I loved going through that process with you, Oscar.

Oscar Trimboli:

The reality for me was because I didn’t take you through enough of the backstory, the context was the [inaudible 00:47:04] But I think once you got into the context of the jigsaw puzzle, and it all made complete sense to you. If anybody wants to have a transformational research, backed adult learning experience, the deep listening workshop that we’ve run many, many times now is something that people not only say is transformational on the day, but sustains the change well beyond that day as well, particularly in an organisational context.

Nell, the next story I want to tell you about is a story I love. It’s a story about a leader in a professional services organisation. Together, we were trying to figure out, or at least they were, I was the guide by the side, I was their business Sherpa in that case? They were trying to figure out how does Adam, is the person in this case, Adam had basically been running this business for about three years. They had got consistent results. 10% improvement, not to be sneezed at every year.

But Adam, it was mechanical. Nell, if you can picture Adam and if he was sitting right here next to us in this meeting room. We’ve got the whiteboard up there. We’ve got some magic markers and there was a bit of butcher paper left over in the room from the last person who hadn’t cleaned up. Don’t you love that? The room was really tight. Not like this one, bright area and natural light. It was kind of that dusty, musky feel about it. It constrained the thinking.

Anyway, that’s really couldn’t be part of the story, but it is. Adam was explaining the plan from the past and the plan for the next 12 months. This is what Adam said next.


Government never buys in less than six months, and the most established division is at their maximum capacity. There is no growth for us there. Opening new locations is completely out of the question as our shareholders wouldn’t be open to an investment in these areas.

Oscar Trimboli:

Now, Adam provided me with some clues. He provided me some clues about what was absent in what he was saying. He provided me some clues about what was absolute, and he also provided me with what he assumed when he said-


Government never buys in less than six months.

Oscar Trimboli:

This is a great example of an absolute. The use of the word, never, is a great clue for you to go and explore and explore what sits behind the assumption. Hey, Nell, why don’t we stay with the jigsaw puzzle analogy as it relates to Adam in this discussion that I’m exploring with him and listening to him really deeply on visualising a jigsaw puzzle. We’re working down the vertical line, rather than the horizontal line.

For the current edge of the discussion, I asked Adam next, this question, in what context might your statement about never be false? Now, Adam loves the chat. He’s an English guy. He’s from London and you can make all those assumptions you make about the London accent. He paused. He stopped. He was actually stopped in his chair and for the first time and I met with him for a year up until that point, it was the longest pause he’d ever taken.

I sitting there privately cheering myself because I remember my teacher always saying to me that the length of the pause is a sign of the gravity of the question you’re asking. So, I’m cheering myself on, while he’s pausing, but I’m not interrupting, sorry. There’s a little commercial break from Oscars ego. It’s what he said next, which was really interesting. Now, remember the question is this, Adam, in what context might this statement, never, be false? What he said next was.


I’ve not thought about that possibility until now.

Oscar Trimboli:

So, Adam took another deep breath and the gaze of his eyes, which were normally quite fixed on me started to roam around the room and his eyes locked up and away. I could see he was looking around for inspiration. It seemed like an eternity. For most of us when silence is there, we think it’s an eternity. He looked up, he looked at the ceiling, he looked around the room, it was probably only 30 seconds, but it felt like forever. Adam said this next.


Well, I suppose there are government departments, and then there are government departments. What I mean by that is some government departments act and behave more like commercial organisations than government departments. Their objectives and outcomes feel more like businesses than government.

Oscar Trimboli:

In my mind, at that point, what I decided was, can we keep going down the vertical edge of the jigsaw puzzle? If you visualise me coming down the left hand side here, Nell, I wanted to see should we make a turn and go along the horizontal? All I say then is, is there anything else? Now, you notice the inflexion in my voice at the end, because I’m encouraging you with that question. Adam kindly recorded what he said next. This is what Adam said.


I must be honest, there are government departments that do buy regularly in less than eight weeks. It often happens towards the end of the financial year. They realise that they’ve got unspent budgets. In fact, their buying patterns are quite consistent. I should look back in our accounting records for the last three years and-

Oscar Trimboli:

Now, there’s a huge change at this point. If you can visualise, Nell, this big sheet of A3 paper is actually got a pad that he carries around with him. It’s like a sketch pad. The kind that an artist would use. It’s pretty old school in an era of iPads and laptops coming to a meeting. Adam loves capturing diagrams and concepts and pictures and diagrams. He loves to sketch. So, he starts to sketch on this pad, and he starts scribbling with some really thick dark pens and starts scribbling notes and draws diagrams. He’s showing different government departments and connecting each of these.

But what I noticed in these beautiful drawings is each government department is drawn as a bubble. And each bubble has a different size. All the sizes are somehow connected together with arrows and he draws stick figures, stick figures of who he knows in those organisations. I can see Adam’s percolating on this idea, and he is processing in a really visual and very kinesthetic way.

Now, at this point, I’m guessing Adam doesn’t want to go and explore the jigsaw puzzle anymore, he’s probably figured out what he needs to and keeps sketching away. He says, “Please continue, Oscar.” A lot of time, I want them to complete their thought and capture that idea on paper. So, allow him to finish.

Nell, the point I’m making is really important. While you’re sketching, typing, style listening on an electronic device, your visual cortex is engaged, which reduces your capacity to effectively listen. In that moment where other people are taking notes, give them the time to complete their note taking, and that will help them understand their context better.

I’ve waited until Adam finished, and then I simply said, “I’m curious, what are you thinking about now, Adam?” He takes a really long pause, probably longer than the pause before. Now, remember, Adam is someone who loves a chat, and I’m cheering again, because I felt like I finally stopped him in his tracks. He always loved to feel the silence. What he said next really transformed the way I think about the importance of context and exploring assumptions.


Wow, I’m really surprised about how much opportunity sits in just one area of the organisation. I need to think about this more carefully.

Oscar Trimboli:

Helping Adam explore his mental jigsaw puzzle, he was helping him to define the context of his own meaning. It wasn’t there for me to understand the context, it was there for Adam to understand the context.

Nell Norman-Nott:

This story with Adam is fascinating in itself, and how he went on that process of discovery. It was when you said the gravity of the question is in the pause that follows it. I think that’s something that I might take with me to help myself in scenarios where someone doesn’t immediately come back with the answer and you don’t feel like you bamboozled them with a really stupid question.

Oscar Trimboli:

But be careful, Nell, the opposite is true as well, in asking those deep, intense questions, it can come across as intimidating. If they are sequential questions, the person can feel overwhelmed as well. The depth of the question and the gravity and the length of the silence really is getting them to think in parts of their brain they haven’t used before. It’s a bit like asking somebody to lift a set of weights they’ve never lifted before and then asking them to do it immediately again. Sometimes a light hearted question like would you like a glass of water now, might not be a bad thing.

Nell Norman-Nott:

Or a cup of hot chocolate in your case, Oscar.

Oscar Trimboli:

I broke my duck, Nell, on my birthday. Took your hot chocolate out, and made it. Nearly seven months after you gave it to me as a Christmas present.

Context is the map, the jigsaw puzzle that helps you make progress in a conversation while you’re listening. It helps you get through the conversation by taking a little bit of extra time to understanding the backstory. Remember, your context is important. Their context is important, and so is the context of the conversation. Context leaves clues behind in the conversation, Nell, through patterns with the words that they use, with the words that they repeat. Listen to the colour in their adjectives as Adam … Listen to the colour of the adjectives that they use, as Anthony and Sarah and Michael pointed out earlier on. Adjectives are those descriptive words that you speak a lot about the past, you speak a lot about the future. Do you speak in details, or do you speak in concepts and pitches? Do you always speak in the positive, or do you speak in the negative? Do you speak from an internal orientation, or do you speak from an external orientation where you talk about us and we and the team? Or do you speak in detail? Or do you speak in metaphors?

You see, Nell, the adjectives are the clues. Remember, when we’re listening to Adam, the words he used, he used words like never and always. I always say these are the breadcrumbs or the jigsaw puzzle template that you want to use to discover the context of the conversation. One of the patterns you might want to do is to learn more. One of the patterns you might like to do is learn from the experience of others. I encourage you to go and visit, and use the deep listening playing cards, particularly the deep listening playing cards, Sue, at level three, listening for the context and these will help you move from knowing what the context is to being able to embed context listening in everything you do on a daily basis.

You’ll hear questions that others ask, like the question that Charity asked, for a lot of us becoming conscious of the context moves us from listening in black and white, to listening in colour.

In the next episode, you’ll learn about level four, you’ll learn about listening for what’s unsaid. Let’s listen to Alan, as he provides a sneak peek into the next episode.


The third one, which is the most important thing is that recognising through your questioning, and through your senses, what’s been unsaid. The unsaid questioning technique is the most important one.

Oscar Trimboli:

The final takeaway I want to reinforce, if there’s one thing you take away from listening for the context, it’s go and explore the backstory. For extra bonus points, notice patterns. But if you can just take the time to say, where did this all start? The context will fill in and magically, not just you as a listener, but the speaker will have a transformational impact, and impact beyond words.

Hi, it’s Oscar. If you’re still listening now you’re probably a really loyal Deep Listener. I’m building an online training programme for managers in organisations. If you’re a manager inside an organisation of more than 500 employees, I’d love you to reach out to me. Just send me an email. That’s, We want to involve you in prototyping this online course and you’ll get lifetime access to this course as one of the prototypers. We’re only looking for five people to participate in this prototyping exercise and your input will ensure that what we’re building is something that we’re listening to and helpful for you. Thanks for listening. 

Subscribe to the podcast