What Investors Can Learn From the World's Greatest Listeners

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As Jim Collins wrote in his leadership classic Good to Great, the most effective leaders are a “paradoxical blend of personal humility and professional will. They are more like Lincoln and Socrates than Patton or Caesar.”

Similarly, it’s not hard to find quotes about the importance of humility and confidence from the world’s best known investors. Investment Masters Class pulled together a couple dozen of them. Here’s one from hedge fund manager Edgar Wachenheim III’s Common Stocks and Common Sense: “I have made a sufficient number of mistakes in my life that there is little danger that I will become overconfident. In my opinion, a good investor needs to strike the right balance between confidence and humility.”

To many, Abraham Lincoln is the epitome of effective leadership. Here’s a quote from a recent Harvard Business Review article about his leadership style: “He was both merciful and merciless, confident and humble, patient and persistent… He displayed…
To many, Abraham Lincoln is the epitome of effective leadership. Here’s a quote from a recent Harvard Business Review article about his leadership style: “He was both merciful and merciless, confident and humble, patient and persistent… He displayed an extraordinary ability to absorb the conflicting wills of a divided people and reflect back to them an unbending faith in a unified future.”

What I took away from my recent podcast interview with Oscar Trimboli is that this paradoxical mix equally applies to great listeners. Oscar is an executive coach, author, speaker and the host of the Deep Listening podcast, on which he talks with journalists, actors, professors, judges and many others about their perspectives on listening.

Balancing humility and confidence

These great listeners all seem to have one thing in common: they are humble and confident at the same time. Here’s what investors and leaders who want to build enduring greatness can learn from how great listeners balance humility and confidence in their interactions with others:

-      They own their flaws. Great listeners are humble enough to recognize their flaws, yet confident enough to own up to them. Here’s what Oscar says in our conversation:

“A good listener will be distracted and just meander through a conversation; a great listener knows he’s distracted and very quickly gets back into the dialogue… Quite often these people will say: I’m sorry, I got a bit lost, could you repeat that again? […] It takes a great deal of humility to admit you got lost in a conversation.”

-      They are eager to learn and willing to change. Great listeners are humble enough to admit that they don’t know everything, yet confident enough to ask the questions that help them learn and grow. As Oscar puts it, listening requires a “willingness to change your own perspective rather than to change the perspective of the person speaking.”

-      If they don’t understand, they don’t pretend. Great listeners are humble enough to realize that they don’t get it, yet confident enough to seek clarification and challenge jargon. Oscar:

“The expert in the room is only useful if he can explain it to non-experts… Quite often people will talk in jargon and language that’s very specific to their industry. In the past, I would just let them finish and ask a completely different question to kind of move the topic on. Whereas now, if someone is explaining a very complex issue to me, I say: my five year old is called Ruby… if she was in the room right now, how would we explain this to Ruby?”

-      They don’t accept distractions. Great listeners understand that they’re easily distracted and they’re not afraid to demand the right circumstances to listen. In my journalism years, it happened once or twice that a CEO wanted the interview to take place at his desk while he was looking at his computer. Of course, I didn’t accept that. As I wrote in a previous blog:

“Listening is not something you do on the side while skimming the front page of the newspaper or checking your phone. Listening requires full commitment and deep focus. Also, beware of internal distractions. You need to be locked in. If you are in a rush or otherwise stressed, it’s better to suggest another time to listen.”

Listen to yourself before you listen to others

In a recent conversation with Dr. Marshall Goldsmith, CNN anchor Chris Cuomo explained why listening is the most neglected communication skill of all: it’s not about us. Speaking is about us, and that’s why it so easily comes to mind when we contemplate personal development goals. But listening is about the person on the other side of the table.

Paradoxically, great listeners first listen to themselves before they can listen to others. In his Deep Listening white paper, Oscar explains that you “need time to tune in and recognize what is running through your own mind, then clear away this clutter and create space to make room to hear others.”

As Oscar suggests in our conversation, you can practice this as you walk from one meeting to the next. Instead of checking your phone and answering an email that could have waited for another hour, just breathe deeply and listen to what’s going on in your head.

In our busy lives, it takes confidence to claim that space, but we need to be humble enough to realize that we need it.