How to Improve Your Listening Skills and Why You Should, with Oscar Trimboli

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Warren Buffett famously took a public speaking course when he was young, and he once said that honing your communication skills is the easiest way to improve your worth by 50 percent.

Personally, I’m not sure about that number, but I do agree with the underlying idea. Communication skills are tremendously important. And one of the most important – if not the most important - skill to master is listening.

That's especially true for investors. Think about the interview-like meetings you have with company management, client meetings or team discussions in which you challenge your colleagues’ investment cases. If you want to succeed in those settings, it all comes down to your ability to listen.

It's also crucial for managers. If you are leading a team and want to increase diversity of thought to reach the best investment decisions, you have to create space for other people’s perspective – which also comes down to listening.

Still, most people don’t get training to become better listeners. Former CNN anchor Chris Cuomo once beautifully explained why this is the case. Listening is not about us, he said… Speaking is about us, and that’s why it so easily comes to mind when we think about personal development goals.

Building on that thought, listening is about the person on the other side of the table – and that’s exactly what makes it so challenging to most of us.

As management thinker Stephen Covey said: “Most people do not listen with the intent to understand, they listen with the intent to reply.” We compare the speaker’s story with our own experiences. They talk about their holiday to Spain, and we respond by talking about our trip to Italy. Or we judge or evaluate what they have to say, overlaying their story with our own perception of reality.

So, how do you listen?

Today you’ll hear from one of the world’s leading experts in this field. Oscar Trimboli is an executive coach from Australia, the host of the ‘Deep Listening’ podcast and the author of the newly published book ‘How to Listen’. 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.

In this episode, Oscar breaks down the art of listening. You’ll learn about the importance of listening, where to start when you want to improve your skills, how to get into the right mindset to listen in meetings and why listening is so incredibly difficult to most of us.

Oscar Trimboli is an executive coach from Australia, the host of the ‘Deep Listening’ podcast and the author of the newly published book ‘How to Listen’.

Listening guide

I originally recorded this conversation for my podcast series Meeting Strategist in 2018, when I was at the beginning of my podcasting journey. I shortened it a bit for the purpose of The Happy Investor, but it still runs well over an hour. If you don’t feel like listening to the whole thing, below you’ll find time stamps, so you can move back and forth to the sections that are most interesting to you.

“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.”

- Oscar Trimboli


Time stamps:

3:38 – Defining deep listening as a willingness to change

5:06 – The role of interpretation and assumptions in deep listening

6:54 – Eagles and snakes: how listening to the unsaid can make a world of difference

11:20 – How Dr. Bronwyn King used her listening ability to convince pension funds to sell off $8 billion in tobacco shares

13:46 – “If you don’t challenge jargon, you miss out on big opportunities”

15:48 – Reframing and simplifying to help fund managers connect to the emotional element of an otherwise rational profession

20:00 – Dr. King’s mindset to move beyond her frustration and anger

23:56 – The impact of power dynamics on listening

25:00 – Why leaders should demonstrate what good listening looks like

28:51 – What doctors (and other expert powerful people) can do to encourage listening and what they can learn from nurses

34:58 – Speed is great but it comes at a cost: options not explored or options not explained

36:55 – Silence and how-based questions: tips for leaders to help other people think 

39:39 – Code words you hear when people think beyond the obvious 

41:58 – When it’s time to stop listening and move on

44:32 – The difference between a good and a great listener

45:50 – How pattern recognition helps you explore what’s unsaid and create breakthroughs

49:58 – Getting in the right state of mind to listen (tips to apply before going into your next meeting)

52:36 – “A hydrated brain is a listening brain”

53:30 – Oscar’s comfort with silence and his deliberate pauses

59:50 – Can you listen when you’re nervous?

1:02:30 – The right headspace for listening: it’s not about me

1:07:05 – What Oscar learned from the great listeners who appeared on his Deep Listening podcast

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