Deep Listening in the Workplace with Author and Tech Industry Veteran, Oscar Trimboli

How to Build Deep Listening Skills in the Workplace with Oscar Trimboli

Hi everyone, it’s Jenn DeWall, and on this week’s episode of The Leadership Habit Podcast, I sat down with Oscar Trimboli to talk about how to listen in the workplace. Now Oscar is on a quest to create 100 million deep listeners. He is an author, he’s the host of the Apple Award-winning podcast, Deep Listening, and is a sought after keynote speaker. He is passionate about using the gift of listening to bring positive change in homes, workplaces, and cultures worldwide. And I hope you enjoy our conversation and I hope you are also inspired to connect on a deeper level by using listening. So here is Oscar’s and my conversation on how to listen in the workplace.

Meet Oscar Trimboli, Deep Listening Expert

Jenn DeWall:  Hi everyone, it’s Jenn DeWall and I’m so excited to have Oscar Trimboli. You heard about him on our opening bumper. This is the man behind– and I’m holding this up for those that can see our video recording of the podcast– he is the author of How to Listen: Discover the Hidden Key to Better Communication. And I am so excited to be having a conversation on how we can listen in the workplace because I feel like listening and communication is stuff that everyone thinks we should have solved by now. And yet these are the things that we still all have probably a big opportunity to improve upon. But Oscar, welcome to the show. We are so happy to have you.

Oscar Trimboli:  G’day, Jenn. Really looking forward to listening to your questions today.

Jenn DeWall:  Great. Well I just love to get started. I do this at the ever, I guess at the top of almost every show, which is what made you become interested in listening, how did you come to be where you are today? If you could just go ahead and give us an introduction from your words to our audience.

What Started Your Deep Listening Journey?

Oscar Trimboli:  I think you need to zoom into a boardroom that I was in in April, 2008. We recently had bush fires in Sydney at the time and the, the smoke was still in the air conditioning system in the office and I can still feel that feeling. I don’t know if you’ve ever smelt smoke Jenn, but just will stay with you for a very, very long time. And I was on a video conference between Sydney, Seattle and Singapore and in that meeting there were, it was the budget setting meeting for the fiscal year, 18 people all around the world. The meeting is scheduled for 90 minutes, but these meetings are renowned to go for 3, 4, 5 hours because they are the budget setting meeting. You can’t leave till the budget set. Now, something really interesting happened at the 20 minute marker. I’m sitting there in the meeting and my vice president in the room, Tracy looks me straight in the eye and says, I need to see you immediately after this meeting.

Now Jenn, for the rest of the meeting, I did not listen to a single word that was being said in that budget setting meeting because all I thought was I’m gonna get fired and how many weeks of salary have I got left and what are my job prospects. As marketing director at Microsoft at the time. I was completely freaked out at the 70 minute mark, 20 minutes earlier than anticipated. The meeting finished early and as everybody left, I got up and Tracy said, make sure you close the door. And I thought, wow, okay. So I went and closed the door and as I walked back to my chair, she said, you have no idea what you did at the 20 minute mark, do you? And I thought, great, I’m getting fired and I don’t even know what I did. And as I sat down, she said, the most profound thing I’ve ever heard somebody say to me, she said, Oscar, if you could code how you’d listen, you could change the world.

The Quest to Improve Listening Skills in the Workplace

Oscar Trimboli: And Jenn, as insightful, a moment of listening as that was on Tracy’s part, the only thing going through my head was, Woohoo, I hadn’t been fired. I can put all that money back in my bank account and the only thing I could blurt out in that moment was simply this. Tracy, do you mean code or code-code? Because we’re working on Microsoft. I thought maybe she’s asking me to make it into a methodology or or did you really mean software? And she said, code, Oscar code. And since then I’ve been on a quest to code listening and we’ve got a listening quiz. We’ve got three books, we’ve got podcasts, we’ve got jigsaw puzzle games, we have a range of resources to help people understand how to listen in the workplace. Because I don’t know about you Jenn. I didn’t go to a class at school. I didn’t have a subject on listening. Maybe it’s different in Colorado. Maybe it’s different where you went to school. Did you have a listening class?

Jenn DeWall:  I don’t think I ever had a specific listening class outside of a communications course in college. Yeah, I think that was probably the only like exposure that I had ever had to that.

Oscar Trimboli:  In our workplaces by the second decade of most people’s career, they’ve had at least one training in how to speak effectively, how to speak with influence or impact. By the third decade of their career. They’ve had two training courses on that. And for the same statistics, the answer is zero and zero for workplace employees who’ve got any training on how to listen. And it’s no different based on seniority. It’s no different based on industry. And it’s no different based on gender. We struggle with how to listen because we’ve never had any structured training.

We have been taught how to listen. We’ve been taught by the role modeling of our managers, our executive, our parents, our auntie, our uncle, our teachers, our sports coaches, our music teachers, all of them role models, how to listen. And we picked up tips along the way. But most of us can say when it comes to math, there’s add, divide, subtract, multiply. When it comes to language. There’s verbs and nouns and pronouns and adjectives. When it comes to chemistry, there’s a periodic table of elements that’s identical no matter what language you speak around the world. But we don’t have anything like that about listening. In fact, most people can talk with more nuance about cheese or wine than they can talk about their listening.

Jenn DeWall:  <Laugh>. I like that. It’s interesting to think about that given that presumably people are listening more than they are eating cheese or drinking wine, you know

Oscar Trimboli:  Or speaking for that matter. You know, the more senior you are in an organization, the more leadership roles you take, the more of your day you are spending listening. So it’s a superpower you should be building more muscle on. You should know how to do it impactfully. And if you’re in customer facing roles or you are taking a brief, you know, medical situation or a legal situation you are spending more of your day listening, than you are actually talking. So if you want to increase profitability, if you want clients to become your best sales weapons, then if you listen to them, you’ll be very different from anybody else who engages with them.

Who Needs to Improve Listening Skills in the Workplace?

Jenn DeWall:  So, getting into your newest book, How to Listen, Discover the Hidden Key for Better Communication, who is this book for? When you were writing it, who was that person that you had in mind or your inspiration that you really wanted to pick this book up?

Oscar Trimboli:  Rita is the inspiration. We, we actually talk about Rita in the book. And Rita is an energizer bunny. She’s a chief operating officer of a listed publicly traded company. And she’s got so many awards for her leadership. But what she did was bump into a leadership ceiling as Chief Operating Officer. She thought that by speaking faster, louder, and more energetically for her team, she would have a bigger impact. And what got her there wouldn’t get her to the next level of executive. And she had a moment when her chief executive officer had her annual performance review, and like every other performance review that Rita had, she was expecting a stellar performance review. And her CEO simply said to her, Rita, you’re too far ahead of your team. They feel like they’re chasing you, and they don’t know where they fit in.

You are way ahead of the team. Every time they bring you an issue, you are trying to fix it instead of listen to them. And when you are not present as a leader, the results don’t sustain themselves. The difference between a manager and a leader, a manager gets things done when they’re there. A leader gets things done when they’re not there. And Rita had become this really good manager who got things done. She was epic cheerleader. She was the leader who was always there early and left late and she was completely drained and she was struggling to understand, hey, this is how I’ve been leading before. Why am I struggling now? Why am I getting all this poor feedback? And the CEO said something to her that kind of changed the way she thought about it. And this is when she started to explore different leadership approaches that her, her CEO simply said, you’ve got 90 days to fix it, or I will <laugh>.

The Importance of Listening to What People Don’t Say

Oscar Trimboli:  So I don’t, I dunno if that was a veil threat at her role, I don’t suspect it was, but it was very clear to Rita something needed to change in the way she led. And yeah, from that point on, Rita started to explore what’s the other half of communication. And she had to pause and slow down and ask more questions than solve problems. As an example. Now I can tell you today, Rita’s a very successful CEO. Not in that organization, but in another one that’s publicly traded. And she only adjusted her leadership by 5%. And the 5% was exploring not just what people say, but what people don’t say.

When you understand the neuroscience of listening, that is the speaker can speak at between 125 words to 150 words per minute, yet they can think at 900. So if you just listen to what they say, you’re missing out on about 86% of what they think and what they mean. And when you understand that listening is to help the speaker express what they think and what they mean not to help your understanding, all of a sudden employee engagement changes. They’ll give more effort when you’re not there. And customers will refer you because they sense you care not only about the transaction, but also about the relationship. Suppliers will give you e extra effort because you understand their constraints. So when we wrote the book, it was for a Rita.

Jenn DeWall:  I love it. No, thank you so much for sharing that. And I know we’re gonna dive into the barriers cause my head is already going into thinking of some of the challenges that I’ve experienced with listening, right? Such as missing maybe not what’s brought up, but also sometimes not listening at all to what’s brought up is what comes around. But before we dive into that and you know, talk a little bit more about bias or just different challenges within listening, let’s start with that basic definition. I know you differentiate active versus deep listening. What is the difference between the two?

What is the Difference Between Active Listening and Deep Listening?

Oscar Trimboli:  Active listening is really important. Active listening is about hearing what is being said. And typically, you’ve been trained in active listening training if you’ve had any training at all, to nod, to paraphrase, to use nonverbal affirmation to the speaker, to keep eye contact, to not be distracted. And so active listening is about paying attention to what’s being said. Deeper listening is about giving attention and noticing what’s not being said. So you’ll need to progress from active listening into deep listening. And the important part of that is most people focus on the speaker as their first act of listening. And that’s the wrong place to start.

And this is the bit that the active listening movement kind of jumps this step. You need to listen to yourself. Step one in listening is not focusing on the speaker. Because so many of us turn up to conversations, Jenn, with all these browser tabs open in our mind, chewing up our memory, and we’re not available, the next conversation just becomes the overload and our browser crashes in our mind. And we can’t process what’s being said because we’re thinking about the last conversation. We’re thinking about the next conversation. We’re thinking about our next question. We’re thinking about why they’re wrong, and we’re right. All these things are probably going through your head right now, Jenn. Right.

Jenn DeWall:  No, I’m also thinking of, because I, I appreciate that. Because one of the pieces that I loved, like from your book of reading was one of the pieces was talking about even starting when you’re starting with yourself, which is the first place of the diagram or the process of listening. I really appreciated I was the recommendation, the three minutes. By taking the three minutes, could you tell us a little bit more about what that is, when we can get in tune to ourselves and how we’re feeling and how we’re showing up to be more present?

Three Minutes to Better Listening (And Shorter Meetings)

Oscar Trimboli:  Yeah. What I’m about to say next is easy to say. It’s hard to practice, but based on our research, we know that if you apply these three tips over three minutes before you go into any conversation, either face-to-face or via video, it will make a material difference. Not just to how you listen, but also to how the speaker explains their idea. When you do this well, what you will not have is speakers rambling, repeating stories. You won’t have them jumping around. When a speaker notices that you’re present and actually listening to them. Meetings are shorter, they’re more succinct, and they get to the point. Now, I don’t know about you Jenn, but shorter meetings, I would love to have shorter meetings. I would love to have less meetings. But for many people that we’re tracking, when they practice these three things, three minutes before the meeting, they consistently report back to their meetings are shorter because the speaker or speakers in a group are getting to the point.

Tip 1:  Manage Electronic Notifications

Oscar Trimboli:  So here are the three tips. Tip number one, manage your electronic notifications before the meeting. That’s not to say switch them off because in some situations you may not be able to. Okay? Be careful of your connected watch the new evil villain of stealing your attention.

Tip 2: Drink a Glass of Water

Oscar Trimboli:  A tip number two is to drink a glass of water before you go into a conversation. Now, if you love Starbucks and you love coffee, that’s okay. Please also drink a glass of water. It just sends a signal to the place around your ribcage, which is called a parasympathetic nervous system. And it just tells you to relax. In fact, if you are in a meeting that goes for more than 30 minutes, you should be drinking a glass of water every 30 minutes as well.

Tip 3: Take 3 Deep Breaths

Oscar Trimboli:  And then finally, before you go into that conversation, whether you’re clicking into the video conference or you’re stepping into the meeting room, just pause and take three deep breaths before you get into that room or that video conference. And again, it sends a signal to the parasympathetic nervous system to say slow down. And what it does is a result starts to shut down some of those browser tabs in your mind. So there’s available memory for you to focus on the speaker.

Bonus Tip – Recharge with Music

Oscar Trimboli: Now, there’s a bonus tip as well. If you want to do all of that to three minutes worth of music, pick a song that matches the energy you want to bring to the conversation. So it could be a fast tempo song, it could be a short tempo song. It could be a song that’s just instrumental, or it could be with words. That’s completely up to you, the Jenn, I don’t know about you, but music consistently rewires my mind before I go into any conversation. So if I want to recharge my listening battery, which I struggle with two, music is the fastest way for me to plug in and recharge.

Jenn DeWall:  No, I, I am here for music because it just shifts so much! But I want to go back to the pause before the meeting, because I think in the same way that some people don’t want to bring in the chit chat because they’ve got things to do. I could imagine some people initially saying, pause, we’ve got things to do. But you had talked about a story in your book from Google. Tell us a little bit more because from what I am understanding in that example, it was well received. And so maybe I want to bring this up so people can trust instead of saying we’ve got things to do.

Start Meetings 5 Minutes After the Hour to Improve Listening

Oscar Trimboli:  Yeah. In his amazing book, James Clear, who writes about Atomic Habits, says, you don’t rise to the level of your goals— you fall to the level of your systems. And when we think about listening systems, one of the things I would encourage every one of you to do if you are the host of the meeting and you are creating the meeting do not start the meeting at the top of the hour. Start at five minutes after the hour. Here’s why.

Most people will arrive physically on time, and some don’t. They’ll arrive five minutes after the hour, but mentally they won’t arrive until five minutes after the time the meeting commences. So let’s contrast these two meetings, and I am answering your Google question in this example, so I haven’t forgotten. So imagine there’s two meetings. Number one, this meeting starts at the top of the hour. Everybody comes in at one minute, after two minutes, after three minutes after four minutes after, five minutes after. And they all say, oh yeah, I just got back from my last meeting, sorry, I’m late. I I I’ll be ready. Just, oh, the second type of meeting they arrive at five minutes after the hour, the exact same time. And they go, Jenn, I love your meetings. I’ve actually had time to go to the bathroom. I’ve actually had time to get a glass of water.

I’ve actually had time to collect my thoughts. I look forward to our meetings because when they start at five minutes after the hour, I’m ready. And even for those people who arrive late five, after the hour, they will say similar things. Now, which meeting do you want? As the host of the meeting? You can create both meetings. If you’re creating one hour meeting, stop it. Just create 50-minute meetings and give people five minutes at the end of their meeting.

Start Each Meeting with Silence to Improve Listening in the Workplace

Oscar Trimboli: As of well now, in 2015, one of the most commented things in the Google Geist, Google Geist is Google’s employee engagement reports. And, and they commented on meetings with over six people in that year. They asked everybody to commence the meeting with a pause, just with silence that was hosted by the leader of the meeting for a period of time. Depending on the size of the meeting, this could vary between a minute to three minutes. And it was the most commented thing on the Google guide where it was implemented. And what they noticed was the meetings where people paused at the beginning of the meeting and collected their thoughts and just got present to the meeting. Those meetings were more effective and shorter.

Jenn DeWall:  For all of the people that might be thinking, that’s a waste of time. I mean, I, it’s just to hear that if we just slow it down, that we can actually heighten people’s ability to connect and interact. I think that’s a really powerful example. Now, okay, can I have pause and chit chat? Can I do both? Because what do we do when we’re trying to build in the water cooler talk? And of course this is a joke, but I know that’s often one of the things that people might start a meeting at. But do you start with the pause, then do a little networking, then get into the agenda? What would you recommend?

Oscar Trimboli:  Well, listening, situational, relational and contextual. So the answer is, it depends If the team is in an early stage of team formation, the chit chat is gonna be more important than the pause. If that team is at the middle of a project, the pause is gonna be more important than the chit chat. But beware, beware, everybody of people creating false binaries. False binary is chit chat or silence. You can do both. Skilled leaders can invite the opportunity to do both. And here’s the thing that we know from not only the research and from the Google Geist that we we talked about earlier on, is that when meetings are rushed, people come back to the following meeting with a deliverable, for example, and say, Hey Jenn, I’ve brought this back for you. And Jenn says, oh, no, no, no, that’s not what I meant. What I meant was this.

Oscar Trimboli:  And there’s a whole range of rework that has to happen. So that’s in a project context, in a, in a sales context for a customer, that might be the customer saying, no, no, no, I didn’t mean that in the brief. What I meant was this. So you’ve just wasted a whole bunch of time after the meeting where you’ve done all this work that you think is productive. Yet if you are present in the meeting to them and you moved your listening from what they said to what they think and ultimately to what they mean, then all of a sudden not only is the meeting shorter, the project’s shorter, there’s less rework there.

So when it comes to chitchat or silence, one of the things we talk about in the book is listen now for absolutes and, and people setting up binaries like that where it’s, it’s either this or it’s that, that they’re listening to what’s being said, not what’s not being said. Because there are many options. There’s option A and B, there’s option one and two. Yet if you listen deeply as a group, there may be option C, d e, F 1, 3, 5, 7. And the answer is all of those things. But rarely in a meeting does a host take the time to listen to all voices and all options. And initially it may seem the meeting is going slower, but it’ll speed up at the back end much quicker. You’ll deliver high quality output and you’ll do it quicker over the life cycle of any project.

Jenn DeWall:  And people will just feel seen or at, you know, if I was in a meeting where, cause I’ve sat in multiple meetings throughout my career where either you’re, you sit behind the boardroom table and that’s your designation. They still want you to participate, but yet you’re, you’re behind them sitting at the conference table. And even just having that inclusive feel, I think changes the entire, I guess, morale that I would ever have in any of those types of meetings.

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The Four Villains of Listening

Jenn DeWall:  I know that at the top we had talked about Rita and going into the obstacles. One of the pieces that the book dives into is that not everyone listens the same. Tell us a little bit more about what we need to be aware of as leaders in terms of understanding how we all listen a little bit differently. You talked about listening for absolutes, but I know in the book you also explored a few other examples of what that looks like.

Oscar Trimboli:  We’ve been lucky because we’ve got this wonderful evidence base when people can complete the listening quiz. They tell us what gets in their way when it comes to listening, as well as complete 20 questions that they answer as well. And what typically happens is there’s four things that get in people’s way and we labeled them, or the people who took part in the research actually labeled them the four villains of listening. Dramatic interrupting, lost and shrewd. Now, I just spent a little bit of time with each of those because I’m a shrewd listener at work and I’m a lost listener at home. My brother-in-laws every Sunday they bang on about religion over and over and over again. And I’m completely lost in the conversation. And the religious debate they have is the religion of, of canon photography versus Nikon photography. It’s just religious fervor in the way they approach it.

The Lost Listener

Oscar Trimboli:  And my idea of photography is my phone. It’s like, it’s, it’s not something I’m interested in. And when I’m lost in that discussion, I feel like what’s my purpose in the conversation? I feel like, gee, I must be coming across as really vague. I’m distracted really easily. And that’s what the Lost listener struggles with their position in a conversation. So imagine a group meeting where you’ve been politely invited as a participant, but given no context about your role, one thing the lost listener should ask the host is, what role do you want me to play in this meeting? If you ask that question, all of a sudden you have a focus for not only your listening but your attention during that meeting. Now, as a shrewd listening villain myself, and the reason I want to pull me apart is that everyone somehow thinks I’m a perfect listener.

The Shrewd Listener

Oscar Trimboli:  I’m like all of us. I’m struggling with it too. I just want to get a little bit better every day. Shrewd listeners are problem-solving machines. They have spent many, many, many, many years in deep study, shrewd listening. Villains are disproportionately represented in consulting professions, legal, accounting, human resources, it anybody who supports functions in the business. And what they’re doing is they’re jumping ahead. Whatever the person’s saying they are jumping ahead and going, yeah, yeah, I know that problem, I can fix that. And I’ve got three others that you haven’t even said, and I’m gonna help you with those too. But what the shrewd listener is not doing is they don’t notice this. And this is what the speaker says about the shrewd listening villain. They say they’re trying to fix me, they’re not paying attention and they’re trying to fix me. And they’re actually trying to fix the problem.

But it is the perception from the speakers. Because we also research the people speaking as well as the people listening. They say, the shrewd listening villain is trying to fix me. The shrewd listener should spend more time listening to how somebody’s saying it, as well as what they’re saying. So shrewd listening villain is very good at synthesizing the content and solving the current issue that they’re missing enormous nuance in what’s not being said.

The Interrupting Listener

Oscar Trimboli: Now, the interrupting listening villain values time. This person you mentioned earlier on, Hey, we’ve got an agenda and there’s no chit chat. That’s likely to be the interrupting and listening villain. They’re the quiz show contestant on jeopardy that presses the buzzer before the complete question is being asked, asked, and they get the wrong answer. Right? So for them they value time and, and time is important, don’t get me wrong. And time is the only finite resource that we really, really have.

What the speaker says about the interrupting listening villain is, can’t you just wait? Can’t I just say it fully? Why? Creating friction in our relationship, you’re too busy on task and you just need to wait. Just count one 1000, two 1000, three 1000. And you’ll notice when they take a breath, it’s not a pause, they’re just collecting their thoughts to finish the sentence.

The Dramatic Listener

Oscar Trimboli: The final one is the dramatic listening villain who, who connects emotionally. The emotion is the primary way they form connection in a dialogue. Hmm. Jenn described it as a chit chat, how to do the relationship bit. The beginning. What they do is you’ll say to a dramatic listener, I’m really struggling with my manager when they turn up to my meetings for one-on-ones, they’re always late and most of the time they don’t turn up at all. And then the dramatic listening villain who’s trying to form a connection but just moving the spotlight off the speaker onto them will say, wow, you think you’ve got a bad manager? Let me tell you about the worst manager I’ve ever had in my life. And off they go. And they, it’s like, same with the merger, same with a terrible customer. There’s all these situations, what the speaker says when they’re interrupting with the dramatic listening villain is simply this.

It’s all about them. And as a result, I’ll say less and all they’re trying to do is form a connection, but they’re jumping too far and they’re moving the spotlight off the speaker and onto themselves. So when you think about the worst listener, you know, they will have elements over all of those dramatic interrupting, lost and shrew. Which one of those can you relate to the most, Jenn?

Jenn DeWall:  I feel like I would probably be more dramatic, but I think because of my younger experience, like, cause I’m very sensitive to other people’s emotions in that regard. I think I attached to that. I think because of my upbringing, I’m relatively like decent at making sure to keep the spotlight. But as you were saying that, I have a friend that I adore <laugh>, but I like was thinking and I’m like, oh my gosh, this is her. I really love her. But I know sometimes she can rub people the wrong ways because I hear it almost as they describe her as a one upper, like, oh, you went to Australia? Well, I’ve been to Australia 10 times. Oh, you ate this? Well, I ate that, you know, at five different restaurants. And I love her. I’ve known her for over 20 years, so I know how she is. But I think if I had to put another name on it, I’m like, that’s what it’s <laugh>.

Oscar Trimboli:  I like, I like that. The one-upper

Jenn DeWall:  Yes. It’s oh my gosh. Like I’ll spare anymore. Because I do love her. But yeah, she, that’s just, and it’s actually to me because I, I find it endearing. Like I know who she is and yeah, I guess, you know, so I find it endearing, but at a workplace that would actually drive me bananas because I would not feel heard and yes, like having it feel like, oh, so it’s about you even though it’s not. And I think full transparency, that many years of therapy that I’ve done throughout my whole life being very mindful of how you’re supposed to approach someone when they are explaining something that’s sensitive and like keeping that spotlight in them. Like that’s something I’m probably more hypersensitive to in emotional situations. I’m probably not gonna be like, oh, you went through this traumatic thing. Let me tell you about mine. But she might do that, and I love her, but she might do that. Let’s talk about the role of bias in the workplace. What role does bias play as it relates to listening?

How Does Bias Hurt Our Listening Skills in the Workplace?

Oscar Trimboli:  Well, we’ve already spoken about the four primary biases that get in people’s way, emotion, time, relevance to the conversation and problem-solving. And for many of us, we are not conscious of some really simple biases. I I, I’ll give you a very practical one. One bias is do you listen for similar, the familiar or do you listen for difference? Most of us, because of western education systems, because of the scientific method, we are trained to listen for similarity. We don’t know this, it’s a subconscious bias, but the scientific method says, do an experiment, find data, improve, do an experiment, find data, improve in law, you use case data and the history of case data to support the way you do something. You are listening for similarity. You’re not necessarily listening for difference. And for most people, we do a survey in our workshops all around the world, and it’s pretty consistent.

Nine out of 10 people will self-identify as a listening for similarity first and listening for different second. Now again, be aware as I mentioned earlier on, if somebody’s setting up a false binary similar, different is a good example of that there is an option called both. And, and we’ll talk about that as well. So when you think about buyers, I want you to come with me to a story with Christopher and, and Jennifer. And they, they live in Minnesota and Jenn, a stay at home mom. And Christopher was coming home from junior school and he said, mommy, mommy, I’m so excited today I learned that three is half of eight. Now Jennifer thought she misheard him and said, honey, could you say that again? And he said, yes, mommy, we learned that three is half of eight.

Oscar Trimboli:  Jennifer thought, Hmm. So she went to the kitchen cupboard and got out a packet of M&Ms and she laid out four M&M chocolate soldiers in one row and four m and m chocolate soldiers in another row and had them facing each other. And she asked Christopher how many M&Ms, and he went, 1, 2, 3, 4, and 1, 2, 3, 4. And she explained to him, you see four, not three is half of eight. You see with that, Christopher jumps off the kitchen bench, gets a sharpie from the corner cupboard and draws the figure eight on a piece of paper. And what he does next is he folds the piece of paper in half and he tears the piece of paper in half and shows his mom two perfectly form threes. And in that moment, Jennifer’s world changed because she just discovered that three is half of eight.

Now, what’s even more interesting, Jenn, is if you turn the eight sideways, tear the piece of paper horizontally, zero is half of eight, three is half of eight, and four is half of eight. Now, when we listen for similarity, what we do is we go, you’re wrong, you’re wrong, you’re wrong. Four is half of eight, four is half of eight. Four is half of eight, you’re wrong. And yet when you think in geometry, which is what Christopher meant, not what he said, there are many, many, many possibilities. Zero is half of eight, three is half of eight, four is half of eight. And there are many other options in there as well. But for most of us in workplace conversations, because we listen for similarity, we’re in judgment going, you’re wrong, you’re wrong, you’re wrong. Have you ever had a three is half of eight moment in the workplace, Jenn, that you kind of go, oh yeah, that’s where my bias showed up.

Confirming the “Afters” to Improve Listening in the Workplace

Jenn DeWall:  Absolutely. I think I had one even a month ago when I was working with someone and misunderstood the deadline that they were setting and the deadline that they were setting. I interpreted it as we wanted this basically yesterday, even though I just got it. And then I spent 12 to 14 hours to do it. And then when we came back and I was frustrated in our follow-up conversation that I had had such a low turnaround, and then it was the, you know, the three, three is half of eight moment. No, this was the piece that I thought you would want, not this entire thing that you, and absolutely, yes. And there was a lot of pain in that moment as and frustration as I was, you know, scrambling to get this done because I wanted to do it. The, I just didn’t understand the scope. But yeah, that was absolutely the moment, <laugh>

Oscar Trimboli:  And, and for many of us, we don’t confirm with the speaker what they want. And you’ve used a beautiful illustration there of, in our rush to be on time, we actually missed the deliverable because it wasn’t what they meant, it’s what they said because we interpreted that way through our own lens. But a simple question, would be, so just to confirm, could you outline the deliverable you’re expecting tomorrow? Yeah. That it would’ve had a completely different conversation and you would’ve got 14 hours back in your life, <laugh>, that you’ll never get back again, right? But, but for many of us, what we, what we choose to do is think that listening is about understanding what the speaker said. When we listen effectively, when we move beyond active listening, and instead of just paraphrasing, we will go back and check with the speaker what they actually meant.

Oscar Trimboli:  But if your browser tabs are full in a conversation, you won’t even have the state of mind in place to go, oh, I have to check that. You’ll just do what, what you just did. Thanks for sharing a beautiful and common example of when people struggle with the difference between spoken and what the meaning is actually there. And just remember, if you can take away that 1 25, 900 rule, you can ask three questions that will help you and the speaker. And I think that’ll be helpful for you Jenn, as well. As those listening, these three questions go in different directions.

Using A Compass for Better Listening Skills

Oscar Trimboli:  If you think about a listening compass, I’m gonna give you a north-south question. North-south questions continue and they help you to listen for more similarity, the more familiar. And now I’m gonna give you an east west question, which will help you listen for difference. And then I’m gonna give you a really powerful technique, the third technique. And this question’s the shortest question of all. So the north south question is a version of, tell me more. Now, if you just use, tell me more in a conversation. And people aren’t used to you using very short language like that, they may get confused and may think it’s an interrogation. So make a humor, make it personal. Wow. Jenn, I’m, I’m fascinated. Could you say more about that? And they will continue talking in a similar way to the issue.

The sequence is probably like this, east, west, next north, south, first, east, west, next we want to ask a question for the difference. And it’s a version of this. And what else? I’m fascinated, is there anything else you’ve considered? Is there anything else you want to explore? Is there, you get the point, but what we’ll do, we’ll move the speaker’s time horizon. Now this is the version of the question I use when I’m working with a client. I simply say this and insert whatever element of this question makes sense for you. I will say, Jenn,

Oscar Trimboli:  If your manager was in the room, what’s the question we should have asked ourselves that we haven’t? Jenn, if the shareholders were in the room, Jenn, if the founder was in the room, Jenn, if the customer was in the room, Jenn, if the supplier was in the room, Jenn, if the regulator was in the room, Jenn, if the media was in the room, pick whatever version of that question is helpful for you. Maybe a supply for example, or an employee. But what it does immediately, it stops the speaker immediately and they go, oh, okay. And then they bring up a question that we haven’t discussed it maybe one or maybe two, maybe three. And because we’ve raised it in this discussion, they will raise it in the next discussion with that person. But more importantly, we have gone in a completely different direction in this conversation and we haven’t wasted our time. East west questions should not be asked any later than 40% of the way into the meeting. because then it’s too late, you won’t catch it. If it’s your last question, you’ve missed a massive opportunity.

The Moment of Silence

Oscar Trimboli: Now the final technique is the most powerful and done well. It’s liberating, done poorly. It’s intimidating. Here it is a listen carefully because it’s really short.

Now don’t worry, no microphones froze or no video froze. There’s no coincidence that the word silent has the exact same letters as the word listen.

In the West, we have this interesting relationship with silence. We call it the pregnant pause, the awkward silence, the deafening silence in high context cultures, cultures that value the relationship above the task. China, Korea, Japan, the Inuit of North America, the indigenous communities of Australia, the Maori of New Zealand, the Polynesians of the Pacific. Silence is a sign of wisdom, respect, and authority. And simply holding space with silence will show to the speaker you value them, you see them, you hear them, and you’ll want to hear what they’re thinking as well as what they’re meaning.

Jenn DeWall:  I love that we did another pause after that one too, <laugh>, because I will say that that is, you know, especially when I’m nervous, that can be, and I’m sure someone else listening likely has that, that can be the harder piece is to incorporate that pause. I can get that, you know, the anxiety can start to tick up with the pause. But I appreciate even just the different considerations of the value that the pause brings because I, I know I need that reminder. It just because it is such an instinctual, oh, this is uncomfortable.

Holy cow. Okay, better say like 25,000 things that don’t make sense and might derail this. And then I can go and kick myself for it later because I should have actually just embraced the pause. <Laugh> Oscar, I really enjoyed our conversation. I know that we, we could have absolutely carried on for much longer, but could you go ahead and tell our audience how they can connect with you, how they could book you, how they could work with you, where they can get the book, all of the beautiful things or any final messages that you would love to share with them.

Where to Find More From Oscar Trimboli

Oscar Trimboli:  I’d love it if you connected with me, but I’d rather you connected with your own listening in the book How to Listen. We give you directions to where you can take a 20-question assessment. It’ll be done maximum has ever taken anybody. Seven minutes. Typically it’s gonna take you five minutes. You’ll get a report as well with your primary villain. The book itself will help you go through some of the things in enormous detail. And one of my favorite quotes from an Amazon review about the book was listening. It’s like sex and comedy. We all think we’re better at it than we really are. So I believe if you’re good at listening, you are also good at comedy and sex. But you’ll have to read the book to find out.

Jenn DeWall:  Thank you so much, Oscar. I loved our conversation, and to bring it back, thank you so much for coming on the Leadership Habit. That was a great Amazon review. No, but thank you so much for being on the show. Thank you so much for taking the time. And I mean, hopefully we can all make bigger, we can have better meetings and have better relationships with people if we just focus on how to listen. Thank you so much for being on the show.

Oscar Trimboli:  Thanks for listening.

Thanks for Listening to The Leadership Habit

Jenn DeWall: Thank you so much for listening to this week’s episode of the Leadership Habit Podcast. I really enjoyed my conversation with Oscar and I hope that you did too. Now, as Oscar mentioned at the end of the show, you can go to, and there you can find out more about your own unique listening style.

And if you want to connect with Oscar to learn more about what he does, and find out more about his books, you can head on over to Thank you so much for listening. If you enjoy today’s podcast, please leave us a review on your favorite podcast treatment platform. And, of course, if we at Crestcom can help you in any way to develop you or your team or your organization’s leadership skillset, add on over to We would love to come into your organization and offer a two-hour complimentary leadership skills workshop. Until next time.