Podcasts- Project Good Boss

EP12: Oscar Trimboli on Listening and Leadership


Author, host of the Apple award-winning podcast Deep Listening, and a sought after keynote speaker, Oscar Trimboli has spent his professional career dedicated to the empowerment of better listening.  His work in leadership teams from around the world has focused greater attention on building and fixing organisations to make impact , creating powerful legacies along the way. He’s a good boss and a good egg, so listen in to hear Oscar chat everything from meditation retreats to female leadership during the Covid pandemic. Yep, we went there!


Intro  0:00

You’re listening to Project Good Boss, the podcast, with your host Anna Sheppard.

Anna Sheppard  0:22

Project Good Boss is a podcast dedicated to understanding the business benefits of kindness in leadership. We cover topics including, and not limited to, leadership, equality, psychology, social impact, decent work and economic growth. All delivered with a little splash of good vibes.

Today on Project Good Boss, we will be spending time with Oscar Trimboli. He’s an author, host of the Apple award-winning podcast Deep Listening, and a sought after keynote speaker. He is super passionate about using the gift of listening to bring positive change in homes, workplaces and cultures around the world. Through his work with chairs, boards of directors and executive teams in local, regional and global organisations, Oscar has experienced firsthand the transformational impact leaders and organisations can have when they listen beyond the words. He believes that leadership teams need to focus their attention and their listening on building organisations that have impact and create powerful legacies for the people they serve today, and more importantly for future generations. He is a marketing and technology veteran with over 30 years experience across general management, sales, marketing and operations for the likes of Microsoft, PeopleSoft, Polycom, Professional Advantage and Vodafone. He’s worked with some of the world’s biggest corporations. And he lives here in Sydney with his wife Janine, where he helps first-time runners and ocean swimmers conquer their fears and contributes to the cure for cancer as part of Come To, a cancer research charity. A general all-around good egg. We’re really really proud and we’re very lucky to have Oscar Trimboli join us today for Project Good Boss.

Hello, Oscar. Welcome to Project Good Boss.

Oscar Trimboli  2:21

G’day Anna. I am looking forward to listening to your questions today.

Anna Sheppard  2:25

So I’m really excited to welcome you and learn a little bit about what made you a good boss. And I know that’s not really a term you would use for yourself. But I’d love to learn just a little bit about your story. Tell us where did ‘Oscar’ come from?

Oscar Trimboli  2:42

Yeah, I think there’s a lot of elements that went into making me into someone who could help create other leaders. Boss is an interesting term, don’t you think, it implies a certain degree of hierarchy and power over the other. And I learned very early on through sport, through my dad’s work ethic, through my mom’s work ethic, and starting to work hard to help others out. I grew up in a migrant community, we all had to help each other out. And watching my parents do that from very early on. But I guess I was lucky, Anna. I was lucky because my first four bosses in the workplace were all women.

Anna Sheppard  3:32

Hmm, interesting.

Oscar Trimboli  3:34

And it wasn’t ’til I was about 28, that I experienced my first male leader and I was very lucky with him as well. Because he was somebody who lost his dad very early on in life and his mom was a huge influence on the way he led. So Steve displayed a lot of really human characteristics that people tend to associate with women. But what I found with Steve, it was just him. He wasn’t trying to pretend to be somebody else. He had this really hilarious, infectious laugh. He told the worst jokes, but because he laughed at his own jokes, you couldn’t help but want to laugh along with him. And I think the first time I ever learned anything about leading others was when I was in sporting teams, where – I was in leadership roles in sporting teams growing up. And what I learned really quickly is lead by example, never ask somebody to do something that you’re not willing to do yourself. It doesn’t mean you do it, but at least be willing to do it as well. And I’ve always had a passion in the workplace for next-generation leaders. And when I was a Microsoft, I got really frustrated. I was volunteering on a graduate recruitment stand at a university and people were just going past the stand and not even paying attention to what we had to offer, because they thought everybody at Microsoft were software programmers, but they weren’t. They were human resources professionals, or finance professionals, they were accountants, they were lawyers, they were Customer Care people, they were salespeople. And yes, they were software developers as well. But I got so frustrated with the situation. I went to my leader at the time, Tracy and I said, our employment brand is broken, I’m going to come back in a month and show you how we’re going to rebuild. That rebuilding of that story really lit a flame in me about building next generation leaders. And as a result, that program ended up getting taken to 26 Microsoft subsidiaries around the world. And that program started way back in 2008. It’s in its 12th year now and still going strong. And the kinds of graduates they are attracting are amazing and really engaged people. So I think I’ve been fortunate in my journey, I’ve worked for amazing organisations that typically were growing. And my best lesson came in the worst environment. I was working at an organisation called Vodafone, they make the connections for people across the world – it’s the largest mobile phone carrier in the globe. Originally from the UK, it came to Australia – extraordinarily unsuccessful in Australia. Third to market in this market and has never really recovered. It’s been operating in the market for 20 years. And the time in which I was part of Vodafone, the corporate culture was very toxic. The fighting within teams – the fighting across teams, the fighting between the leaders and the executives. It was like a Game of Thrones, it was life and death battles and it was very political. And in that, I learned what great leadership is, and what great leadership isn’t. I learned mainly from the absence of leadership, a lot of political maneuvering, no focus outside the organisation. One of the things that struck me one day while I was working at Vodafone was it was about 4:30 in the afternoon, Anna, and I realised in every meeting I’ve been in, we never spoke about a customer once. We were always talking about infighting.

Anna Sheppard  7:34

And you know, it’s really awesome that you’re sharing these honest stories and the different places – I remember Vodafone. I remember, the first phones I had, you know, the little Nokia with Snake on them, and what have you, in the UK and you’d – it’d take you about 10 minutes to write a text message because you have to use – There was no auto-prediction or anything like that in those days. Yeah, so speedy fingers. So, you know, you’re not the first person and you won’t be the last to tell me about toxic cultures that they’ve been involved in. And would you say that that’s been a factor that’s actually pushed you forward to make a decision to try and change some of these cultures, and to try and change the way some of these leaders actually lead?

Oscar Trimboli  8:16

I think the paradox of being inside of one of these organisations or a leader who isn’t self-aware enough to understand what they’re creating is – they think it’s normal. And sometimes the act of you just coming in from the outside and painting a different perspective, a different picture, explaining how this might work differently in smaller organisations, in larger organisations, in overseas organisations. In organisations where English isn’t the language, the spoken might be Portuguese from Brazil, it might be Japanese. And all of a sudden, you can create a perspective for these people, because everybody who goes to work, wants to do their best work. Whether that’s the leader, whether that’s the people who work with the leader, they want to do their best work. And I think for a lot of us, we don’t know what it looks like, because we might only know what it looks like when it’s really done poorly. But those things help us develop muscles and memory. And that can be good. And that can also be unproductive as well. So we just need to be careful.

Anna Sheppard  9:33

And with those people that do go in and try and make a bit of a change in certain organisations can end up themselves being slightly extradited. If you found that – if an organisation does have a culture of toxicity with the way that they operate, like you said, never once spoke about the actual customer, and nevertheless how each of us might actually be doing. What advice would you give to those that are trying to champion change in organisations and trying to make organisations kinder, and cultures more accountable? What advice would you give to those people that are fighting the good fight but a little bit on their own?

Oscar Trimboli  10:16

Yeah, when you look at systems theory, the likelihood you can change a culture only from within is very low. The correlation that internally-driven culture changes sustain themselves beyond the leaders that are implementing the change of the correlations is about point three (0.3). You got better odds flipping a coin, then you have of changing a culture solely from within. So if – my learning has been consistently, and that’s why I use the customer regularly, that’s why I use the competitors regularly, I might use the suppliers, the regulators, the media, or something as simple as asking somebody, “Hey, I’m just curious if your mom was watching us in this meeting today, would she had been proud of how we showed up?” Just something that’s going to draw people out of their current reality and go, “What’s the external perspective?” I always remembered in the early days, the eye rolls I would get when I would say, “We asked a customer about this, Yeah?” And people go, “Oh, here he goes again with the customer.” It’s like, “Come on, Oscar, we’ve got research, the research is quite clear.” I say, and I’d always say, “Research is interesting. But research is a line on a graph.” We could log in to the contact centre and actually listen to the customer’s calls. And we’d probably learn something even more. Because I always find that stories, not statistics, are the things that hook you in with your head and your heart that makes you explore the possibility there. So I think, tell stories from the outside in rather from the inside out, that’s my biggest learning, but it also gives people something to aspire to, something that might be something useful for them, too.

Anna Sheppard  12:13

And I think what’s interesting is we’re finding more leaders are looking for MORE with regards to their leadership journey and their own development, and are starting to make more links and correlations between their own wellbeing, finally, and the wellbeing of their team. And one of those links, I think is, you know, deeper understanding – I’m trying not to use the word spirituality because it scares people off a little bit sometimes, but an understanding of themselves and how they connect to themselves and whatever they might believe in. Could you tell us a little bit about your belief systems and your – how you’ve connected with yourself and how you’re utilizing, you know, your own skillset to be able to share this important message.

Oscar Trimboli  13:00

Beliefs are interesting, aren’t they? My first book that I ever wrote was called Breakthroughs: How to Confront Assumptions. And a lot of us have these mental heuristics that create beliefs and our beliefs are either based on our own experience or teachings. We might be from a secular belief, or might be from a religious belief. You know, for me, I believe in running and swimming. They’re the things that connect me to myself. I believe in walking the dog with my wife, they’re the things that create a connection. I believe in hydration and making sure that you’re drinking lots of water during the day. I believe that nutrition and health and your sleeping is the key to your health. I’m not someone who necessarily believes that you need to sit in a corner at 5:00 AM in the morning and lights some candles and go, “Ommmmmm”. That works for some people – doesn’t work for me. I tried – in a 10 day silent meditation, all I discovered was I found it a very fast way to put my hips out of alignment and got my backside very sore on a cold concrete floor. And it was something fascinating, you were able – say you’d start at 5:30, no 4:30 in the morning, the gong would go off at 4:15 which would give you enough time to do whatever you needed. At 4:30 you’d go into the meditation hall. And this was in winter in the freezing Blue Mountains of Sydney. And so you’d meditate till 6:30 and then stop and have some breakfast, back in at 7:00 meditate, till 10:00, have some morning tea, back in at 10:30 all the way ’till 12 then some lunch. 12:00 ’till 1:00 you got to walk around. That was awesome. Even though some days it was raining and cold. And then follow the pattern all the way until 6:00 PM. By day five, Anna, I went to the instructor. You’re allowed to talk to them between that – when you’re going around for a walk, and the most you could talk to them was for five minutes. And it was fascinating. My hips were so sore, the hip bones were sore,  my shoulders were sore, I’d never done any form of yoga or meditation. So I decided to go from nothing to 10 days of solid meditation. And I went to the instructor and I said, “My hips are really sore, what am I doing wrong?” And all they said was, “Spend more time feeling the pain.” And in my head –  my head’s exploding, it’s like, “How can you say that to me, I’m paying you good money?” Well, it wasn’t actually they only asked for a donation. And it was the best advice I ever got. Because what I took out of that is, FEEL and connect with your body. And I learned nothing about meditation. And then on the last day, the instructor simply said, you know, “Don’t try and do this at home, it’s got to be very difficult to go from 10 days into something that’s a consistent pattern, don’t beat yourself up, but become present when you eat and when you drink.” So for me, there’s always a moment when I have that morning cup of tea, or the morning cereal, where I just pause for 30 seconds beforehand and connect my head and my heart and go, “I’m really grateful for this food, I’m really grateful for this water.” And it connects me as a whole human being. In the west, we spend way too much time only in our heads, and we got to feel what’s in the rest of our bodies. With the leaders I work with every day,  and I would say, generically, if you had to, kind of categorize, men talk less to how they feel about their leadership compared to how women talk about what they feel about their leadership as well. Neither is right or wrong. But I find when people are fully present as leaders, and not putting on masks, pretending to be a leader, and just showing up as them. They’re always connecting their head and their heart. And that’s what the beautiful lesson for me, never sitting down to meditate another hour for the rest of our life. But when I follow the white line running on the road, or when I follow the black line swimming in the swimming pool, or worse still, when I’m looking at seaweed in the ocean, and hoping there’s not a shark there, that’s a form of meditation for me too. And that’s where my beliefs come from.

Anna Sheppard  17:40

Yeah, and I think that’s a great example. Because I mean, obviously Bambuddha Group is all about that balance. But I had a very similar experience in Sri Lanka, where I went on a silent retreat for 10 days, I lasted about three days, and I was like, “Get me out of here.” So I understand thoroughly. And I think, you know, getting that balance around what works for you and not, you know, benchmarking self on somebody else’s things that make them feel calm and balanced is really important. Well, it’s funny, you came on to the men and the women there because I mean, looking at the world, now, we just saw in the news about COVID leaders and the leaders that are really doing well in the world. It’s the women, which quite interestingly, and I’d love to, like, unpack your thoughts around the different leadership styles traditionally shown by women and shown by men, and you know, how we’re getting to a place where we’re starting to understand the importance of that balance at the moment.

Oscar Trimboli  18:36

Yeah, and we need to be careful. Labels are useful, ’till they’re not. And I think if you deconstruct what great leadership is, at the moment, it is clear, consistent communication that cuts through. So that means you’re not talking in sound bites, you’re not talking in political speak. You’re talking to people honestly, truthfully, heartfelt, and in a way that makes sense for them. Now, I’m on a judging panel for a number of industry awards, and it’s often intriguing to me about communications as a skill and the ability to communicate effectively. Well, women balance off the dynamic of communication, half of communication is speaking. The other half is listening. Now, although men and women statistically don’t listen differently, how they listen may vary. So again, women listen to feel and men listen to fix. And when you look at the current situation where the global ecosystem is under threat from an exponential, unknown enemy. A male orientation to fix it may not be a great starting point. So one of the things you saw in countries where the criteria for level one, level two, level three, level four, when it was clearly communicated and provided a roadmap to say, this is the journey, we may go on together, people could go, “Okay, I can see the road ahead.” But it was very clear. Equally, the messaging was very succinct. So when women are communicating this, they have no problems whatsoever being sharp, to the point. Yet, with men, they use all this elaborate language at the moment, particularly in Australia, where it’s, you know, we’re shutting down the playgrounds in public parks, but it’s okay for kids to play in the playgrounds or school. It’s like, “Huh?”. Like, it doesn’t make sense. You can go to someone who cuts your hair for half an hour, but no longer. But you can go and get your nails done, and that can take up to two hours. So I think there’s a big distinction with people who understand that the communication, or how you say it, is just as important as what you say. And as we look around the world, the clarity, the consistency and how the communication cuts through there seems to be a very simple pattern that women who are political leaders in Scandinavia, in Northern Europe, in New Zealand, that communication seems to be working much better than it is for men. But I think that’s combined with a framework of level one, level two, level three and level four as well. So people know where they’re going to be on that journey.

Anna Sheppard  22:04

Hmm, yeah, interesting. And I think the key thing I’m looking forward to as a result of all of this COVID, you know, activities, the sheer amount of DIY haircuts that are going to come out of the other end of the COVID extravaganza. There’s going to be all of these crazy hairdos and all of these leaders that have been leading authentically and a lot of lessons that have been learned. But I think the key things I’ve recognised between the two types of leadership, whether it’s men or women, is owning up when you don’t know the answer. So I think authentic leadership with regards to somebody asking a question, and then saying, “You know what, we don’t actually know the answer to that. But we will find out more, and we’ll update you later too.” Instead of “Actually was a terrible question. We’re not going to answer that one.” Rather than just say, “We don’t know the answer right now.” So I think people can smell, you know, lies and porcupines 100 miles off [inaudible]. And I think authentic leadership is about just being true and honest, at that time, the information that you’ve got, I’d say, and listening. So tell us a little bit about the listening Oscar. Because, you know, deep listening is something that I’ve just learned about through you, actually. And I think having communicated with you a little bit over the past couple of weeks, I’ve never felt more listened to in your presence. So you’ve got this amazing talent with this. What tips and advice would you give to leaders for them to take away, because they’re tuning in for the hacks, let’s face it, but for them to take away, that would make them a truly authentic leader and to be a really good listener?

Oscar Trimboli  23:47

Hmm. I acknowledge the question, I just want to just put a little bit more nuance on leadership in organisations and the organisations I’m working with at the moment around this male-female distinction? One of the last things I’d say, Anna, is I’m noticing the men typically, in their communications will say, “If you’ve got any questions, please don’t hesitate to ask me or your manager.” Whereas the women I’m working with consistently are setting up networks, across teams, and across the organisation to go, “Hey, look, as a leader, I might get sick. Your manager might get sick during this period of time. So if you pair together or find a group of three or four, that would be even better, because there’s redundancy. Why don’t you ask each other the questions you might want to ask us and see if you can solve them together first, and then share them with the rest of the group? Because I don’t have all the answers.” as you mentioned earlier on. Again, I’m seeing a much stronger correlation with women using networks across the organisation in effect outside the organisation. Where the men I’m working with are very focused because they’re focused on the solution. So whether it’s political or in, in workplaces, there are differences to how people are responding. And all rules are false. You know, there’s always an exception to the rule. Just sometimes it’s useful to generalise and take the learnings out of it. I think one of the interesting things for me and around listening is we learnt maths at school. We learned English language at school, we learned science at school. And do you remember your listening classes at school?

Anna Sheppard  25:48

Oh, yeah, good point. I think the only listening class I had was English.

Oscar Trimboli  25:54
And here’s the reality. Yeah, you spent 55% of your day listening, on average. The more senior you are in the organisation, the more of your day you spend listening. And when I work with chairs, and execs, they’re spending up to 83% of their day listening. And yet only 2% of them ever know how. So wouldn’t you want to learn some really basic skills around listening to improve your leadership? And for me, one of the big things that I talk about, people often asked me, “Oscar, what’s this deep listening caper? And how’s that different from active listening?” So active listening was a movement started in the 80s, made popular in the 90s, and basically taught people how to paraphrase and nod. Anna, you make a great point about women in leadership, that would be a paraphrase. And Anna’s nodding right now, while she’s listening to me if you’re not getting to watch this, and you’re listening on the podcast. Now, what active listening taught people to do is to listen to what’s spoken. So whatever is said, you acknowledge and you have the conversation around that. But here the neuroscience of listening, Anna, this is how the brain is wired. I speak at 125 words a minute. If I’m selling real estate, or auction and catalogue, I can speak at about 200 words per minute, and you can still make sense of what I’m at saying 200 words per minute. And you can even listen up to 300 words per minute because blind people who listen to audiobooks and podcasts can listen to up to three times speed and still have comprehension. But as a speaker, I’d have 900 words a minute stuck in my head and a mouth that can only get 125 to 150 words out. So, Anna, what that means is the likelihood that the very first thing I say, is what I mean – here’s 11% chance that what I say is what I mean. So active listening teaches us to listen to the 11%. Deep listening teaches you how to listen to what’s not said. And I know that feels like Yoda from Star Wars just walked into the script. But listening to the unsaid is where 89% of the conversation is, where the meaning is, where the purpose is, where the joy is, where the fear is, where the anxiety is. If we learn to listen beyond the words, projects don’t go off track. Projects don’t go over budget. People don’t have to repeat themselves because they actually are listening to what people mean. So deep listening, Anna, that’s the ability to listen beyond the words.

Anna Sheppard  28:49

Yeah, and I think that’s some brilliant advice for everybody out there. And the leaders out there, especially those that are trying to develop themselves into somebody who’s quite inspirational, but somebody that can really actually help empower and support the people around them. So, Oscar, I’d love us to think about a question that we can put out to our actual listeners today that you think would be a really important question for them to take away and think about for themselves. Got any ideas?

Oscar Trimboli  29:22

We all think the most important place to start listening is focusing on the speaker. That’s the wrong place to start. The most important place to start, when it comes to listening, is listening to yourself. Most of us turn up to a conversation trying to listen to the speaker with our own radio station, playing our own talkback radio session. And we’re not even available to listen. So the research shows with 1410 listeners 86% of us struggle with turning up to the conversation. Listening happens before you even get into a dialogue with a speaker. So the one tip and the one question I’d ask you is, how are you preparing to listen before you talk to the speaker?

Anna Sheppard  30:15

I always find it really interesting with Oscar, you ask a lot of questions and to see what somebody has heard as well. And is that a technique you use to understand how that person is heard and how they’re listening to you?

Oscar Trimboli  30:33

My job is to make sure when I’m listening to somebody that they understand what they’re thinking, not what I’m thinking. If you spend all your time trying to make sense of what someone else is saying, your head will literally hurt. And the most important thing I’ve found is if you ask a question that might sound like, “If we did this interview all over again, Anna, what would be the one question our audience would have wanted us to explore?” All of a sudden, that’s probably going to get you thinking completely differently about how we do this interview as an example.

Anna Sheppard  31:12

And I think that’s a really good question to ask, and maybe we can have you back later down the line to answer any of those questions. How do you feel about that?

Oscar Trimboli  31:20

Yeah, and you know, one of the things we didn’t have time, and maybe we’ll do it in the next one, there are five levels of listening. We’ve only touched on level one today. And that’s all about making sure you’ve got a great foundation for listening as we explore the other four levels of listening. There’s so much amazing nuance in listening to what’s not said, in listening to body language, in listening to stay, in listening to feel, and then ultimately, helping the speaker make sense of what they mean and listening for meaning.

Anna Sheppard  31:55

Thank you for listening to this episode of Project Good Boss. Bambuddha Group is a social enterprise providing leadership coaching for corporate leaders, business owners and operators. We believe in a future where every leader is committed to creating a sustainable world of equality and opportunity for everyone. If you are a game-changing leader, and you have an amazing story of how your business is making the world a kinder and a better place, we would love to hear from you visit on bambuddhagroup.com or slide into our DM’s. And finally, you should know for every paid member we have in our network, we provide scholarships to reduce inequalities in leadership and business. Thank you to Sonic Union for editing this episode, Laura Roberts for writing and performing Project Good Boss and design by Flare Creative. Thank you for being kind today. Thank you for tuning in. And we’ll see you again next time.

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