Exploring the Unsaid: Deep Listening Lessons With Oscar Trimboli – Ep. 04

Oscar Trimboli still finds it uncomfortable to speak about listening, but I’m glad he has found a way to combine these two competing activities. 

Oscar is an executive coach and a listening expert based in Sydney, Australia. In the latest episode of the Meeting Strategist podcast, he talks about the cost of poor listening for individuals and organizations and the importance for leaders – but also for other professionals such as doctors - to listen to what’s unsaid and to those who are reluctant to speak.

This episode runs more than 90 minutes and is my longest to date, but we could easily have gone on for many more hours. One of the reasons why I enjoyed this conversation so much is because Oscar was extremely generous in sharing real-life examples of great listening. This includes the fascinating story of lung cancer oncologist Dr. Bronwyn King who used her curiosity to convince pension funds to sell off $8 billion in tobacco shares.

Before Oscar started his coaching practice in 2013, he spent more than 30 years in general management, sales and marketing roles at technology companies including Microsoft and Vodafone.

I got to know him through his excellent podcast Deep Listening: Impact Beyond Words, on which he interviews journalists, actors, professors, judges and many others about their – sometimes contrasting - perspectives on listening. 

“You would never go to a concert and have your iPhone headset playing while the concert is going on. But all of us literally do that when we bring stories and music in our head to our next conversation.”

To me, Oscar is a true role model for listening. You don’t only notice that in the way he listens, but also – and maybe even more so – in how he talks. Oscar is one of those few people who seems to be extremely comfortable with silence. I shortened some of his longer pauses, but still, there’s more silence in this episode than most of us are used to and comfortable with in our busy lives.


Show Notes:

2:13 – Defining deep listening as a willingness to change

3:43 – Listening on five levels and how it relates to the indigenous people of Australia and China’s Ting character

4:54 – Serena Williams, LEGO, Brexit and broken relationships: the benefit of deep listening and the costs of poor listening

7:02 – The importance of listening in the Big Data revolution

9:16 – The role of interpretation and assumptions in deep listening

11:06 – Eagles and snakes: how listening to the unsaid can make a world of difference

15:36 – “Default option? Do I have an option?”

17:51 – How Dr. Bronwyn King used curiosity to convince pension funds to sell off $8 billion in tobacco shares

19:36 – “If you don’t challenge jargon, you miss out on big opportunities”

21:44 – Reframing and simplifying to help fund managers connect to the emotional element of an otherwise rational profession

26:00 – Dr. King’s mindset to move beyond her frustration and anger

28:05 – The impact of power dynamics on listening

29:25 – Why leaders should demonstrate what good listening looks like

33:03 – The patient-doctor relationship

35:13 – What doctors (and other expert powerful people) can do to encourage listening and what they can learn from nurses

39:00 – Speed is great but it comes at a cost: options not explored or options not explained

41:17 – Silence and how-based questions: tips for leaders to help other people think 

43:58 – Code words you hear when people think beyond the obvious 

46:16 – When it’s time to stop listening and move on

48:51 – Oscar’s listening journey: from his childhood to his corporate career and the start of his coaching practice

51:18 – How Oscar improved his listening skills 

53:08 – The importance of focus and deep breathing: what Oscar learned when training as a coach

54:40 – When Oscar was a good and an atrocious listener in corporate life

58:00 – Being humble enough to say: I don’t understand

1:00:22 – “If you can’t say it in pub talk, don’t say it”

1:01:33 – Why leaders should talk menus rather than ingredients (and why Oscar is serving lasagna around breakfast time)

1:05:37 – Laughing at the iPhone: “Systems that don’t listen do so with a huge cost as a result”

1:06:29 – The difference between a good and a great listener

1:07:55 – How pattern recognition helps you explore what’s unsaid and create breakthroughs

1:11:55 – Getting in the right state of mind to listen (tips to apply before going into your next meeting)

1:14:18 – “A hydrated brain is a listening brain”

1:15:08 – Oscar’s comfort with silence and his deliberate pauses

1:21:50 – Can you listen when you’re nervous?

1:23:50 – The right headspace for listening: it’s not about me

1:28:52 – Teaching 100 million deep listeners globally by 2030

1:31:43 – What Oscar learned from more than 40 episodes of his Deep Listening podcast

Links to people, books and resources mentioned in this episode:

-      Oscar’s LinkedIn profile and his website, where you can also find more information about his Deep Listening book and podcast. You could start by downloading his whitepaper here, as I did

-      His podcast interview with Alan Stokes, a journalist and Lifeline counselor, to which Oscar refers in our conversation, and his episode with Dr. Michael Buist, an academic physician

-      Oscar’s blog about Serena Williams not listening at the US Open 

-      The website of Tobacco Free Portfolios, the organization that started with Dr. Bronwyn King’s inquisitiveness, and her TED talk

-      Books and blogs:

o   Martin Lindstrom’s ‘Small Data’ and Cath O’Neill’s ‘Weapons of Math Destruction’

o   A Washington Post review of Daniele Ofri’s ‘What Patients Say, What Doctors Hear’ book. Also check out my own blog post on challenging doctors to improve medical decision-making

P.S. If you want to help me improve this show, please send your feedback to marcel@meetingstrategist.org