The Importance of Deep Listening Skills for Leaders & Teams
Listening is a skill we all possess, but somewhere along the way, many of us have forgotten how to truly use it. Passionate about the transformative power of deep listening, Oscar Trimboli believes it can bring meaningful change to workplaces and beyond. Through his work with global organizations like American Express, Google, HSBC, and L’Oreal, he helps leaders and teams tune into what’s unsaid—from customers to employees—unlocking potential and fostering understanding.
Oscar is a man on a mission—with a goal to cultivate 100 million deep listeners worldwide, Oscar is not just an author but also the host of the Apple Award-winning podcast, Deep Listening.
The Power of Listening Across Cultures
Listening is more than hearing—it’s shaped by cultural traditions and contexts. In high-context cultures like China, Japan, and Korea, and among Indigenous Australians and Polynesians, silence is a valued part of communication. These pauses deepen understanding, unlike in Western workplaces, where silence is often seen as awkward.
Research shows surprising contrasts: in some Eastern European and South American cultures, talking over someone signals engagement, not interruption. Despite cultural differences, one truth is universal—most people think they’re better listeners than they are. While 75% of people rate themselves as above-average listeners, speakers say only 50% even meet average standards.
Listening is situational, too. Even within organizations, the finance team’s communication style may differ from sales. The key? Awareness, openness to feedback, and the willingness to improve.
The 125 for 900 Rule: Why Deep Listening Matters
Did you know that while we speak at 125 words per minute, we can think at up to 900 words per minute? This gap leaves a lot unsaid, creating opportunities for deeper insights—if we truly listen.
Effective listening in the workplace can:
Boost sales.
Retain top employees.
Foster a culture people genuinely want to be part of.
When leaders focus on what isn’t being said, they:
Increase profits.
Ensure projects are delivered on time.
Attract quality employees through positive referrals.
At the cost of losing customers, damaging your reputation when dissatisfied customers share negative feedback, and facing other challenges.
The 4 Villains of Listening
To be a truly great listener, it's important to not just hear the words but also understand what’s not being said. However, certain habits—called the “villains of listening”—can hold us back. Let’s explore these villains and how to overcome them!
1. The Dramatic Listener
Dramatic listeners aim to create an emotional connection but often turn the conversation back to themselves.
How to Spot It:
You’re eager to share your own story, shifting the spotlight to your experiences.
Fix It:
Pause before jumping in. Ask yourself, Is what I’m about to say about me or them? Focus on keeping the conversation centered on the other person.
2. The Interrupting Listener
Interrupting listeners are time-focused and often jump in too soon, believing they already know what the other person will say.
How to Spot It:
You cut people off, thinking you can answer their question or finish their thoughts faster.
Fix It:
Practice counting in your head: 1-1000, 2-1000, 3-1000. This gives the speaker time to gather their thoughts and finish. Remember, rushing reduces trust and stifles open communication.
3. The Lost Listener
Lost listeners appear distracted or disengaged. They might not know why they’re part of a conversation or are preoccupied with phones or laptops.
How to Spot It:
You feel unclear about your role or purpose in the discussion, or you catch yourself zoning out.
Fix It:
Before a meeting, ask the host, What’s your expectation of me? This simple question can help you stay focused and present. If you do get distracted, acknowledge it quickly and bring yourself back into the conversation.
4. The Shrewd Listener
Shrewd listeners are problem-solvers who appear attentive but are silently strategizing solutions.
How to Spot It:
You nod and say “tell me more,” but your mind is racing ahead, already solving problems the speaker hasn’t mentioned yet.
Fix It:
Focus on how they’re speaking, not just what they’re saying. Stay present and resist the urge to solve their problem until they’ve fully expressed their thoughts.
When Can Listening Villains Be Heroes?
Some "villains" of listening, like interrupting, can actually be helpful in certain situations. For example, interrupting isn’t always bad—when done properly, it can keep conversations on track. In cultures like South America and Eastern Europe, interrupting signals strong relationships. In meetings, interrupting helps when someone’s stuck or off-topic.
The trick is to do it respectfully—wait until they’ve finished speaking, then ask a question like, “If that were a subject line in an email, what would it say?” or “What would the title of that book be?” This can help them get to the point and keep the conversation flowing smoothly. In the right context, interrupting can be a valuable tool—just be respectful and strategic!
Mastering Presence and Focus in Conversations
One of the top skills people aim to improve is their presence—how they show up—and their focus, or how they stay engaged. Presence begins with intention: Are you entering the conversation with curiosity, or are you simply preparing arguments to fire back? Instead of a debate-style approach, consider asking, What will make this conversation meaningful for me, for the other person, and for anyone indirectly impacted?
Practical Tips for Better Presence
Take 30 seconds before a conversation to pause, silence notifications, and clear your mind.
Avoid rushing from one meeting to the next without resetting; presence requires deliberate intent.
Focus not on understanding every word the speaker says but on helping them clarify their thoughts.
A staggering 86% of people admit that devices and mental distractions hinder their presence. Think of it as having too many browser tabs open in your mind. This overload makes listening feel exhausting and unsustainable.
Listening is about creating clarity for the speaker, not just absorbing information. When done right, it becomes a powerful and transformative tool in any interaction.
Here’s a great meeting hack from Oscar: instead of starting your meetings right on the hour or half-hour, try setting them to start 5–10 minutes past. This gives everyone a chance to reset, take a quick break, and arrive at the meeting with more focus. If you can shave 5 minutes off both ends of your meetings, you’ll give people a little breathing room, and the meetings will still be just as productive. Plus, playing your favorite song right before the meeting can help recharge your listening energy and get you in the right mindset.
Just 5 extra minutes can make a big difference in how present everyone is and how much gets done!
Asking Questions with 8 Words Or Less
Oscar also shares another important tip about asking questions and that is to keep them 8 words or less. This is incredibly useful for leaders, especially during one-on-one meetings with team members. If your question is longer, it may come across as more of a statement or assumption, which can shape the answer in a biased way.
So, next time, ask yourself: Can I make this question shorter? A well-crafted question should invite openness, not lead to a presupposed answer.
Do you tune in or do you zone out?
Are you tuning in? Or are you just “kind of” listening? Each of the Listening Villain behaviors is just a label, not your identity. The good news is that you can learn to recognize these tendencies and improve your listening skills.
Take Oscar Trimboli’s listening quiz at www.oscartrimboli.com/listeningquiz to discover your listening “villains” and start transforming how you listen. Once you’ve got your report, send me a copy! I’d love to hear how you’re committing to becoming a better listener.
To sum up everything we learned from Oscar, leaders who excel:
Build a culture of listening.
Listen to what’s unsaid.
Think and act differently, starting with their approach to listening.
Oscar also offers real-world applications and actionable tips to help you listen better in your everyday life. Whether it’s learning to value silence, understanding cultural nuances, or improving workplace communication, his insights are game-changers.
Make sure to tune into the podcast episode for the full interview and dive deeper into the art of deep listening: The Importance of Deep Listening Skills for Leaders & Teams