The Secret Skill That Instantly Makes You More Persuasive, Respected, and Successful

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Most people think they’re good listeners. The reality? They’re just waiting for their turn to talk. And in business, that’s a profit-killing mistake.

We’ve all been guilty of this. You’re in a sales call or meeting, half-listening while crafting your response — or worse, thinking about that trip to Havasu. Later, you wonder why the deal didn’t close.

It gets worse. We do this with our own teams, too. You strut into a leadership meeting, focused on what you’ll say instead of what’s actually being said — then wonder why your team feels unheard.

The truth is, listening isn’t passive — it’s an active skill. And most entrepreneurs are failing at it.

But here’s the good news: great listeners have an unfair advantage. They close more deals, lead with influence, and understand problems before they even arise.

That’s why today, we’re diving into Deep Listening with Eggs! The Podcast alum and world-renowned expert Oscar Trimboli, who has made it his mission to create 100 million deep listeners. In our interview, we discussed:

• The 5 levels of listening — and why most people never make it past level two.
• The tiny tweaks that will immediately improve how you communicate, lead, and sell.
• The one thing you should do in every conversation to unlock game-changing insights.

If you want to build stronger relationships, close more deals, and make people feel truly heard — this is the skill you can’t afford to ignore.

Meet Oscar Trimboli

Image courtesy Oscar Trimboli

Oscar Trimboli isn’t just another communication coach. He’s a former marketing director at Microsoft, an award-winning podcaster, and the author of How to Listen: Discover the Hidden Key to Better Communication and Deep Listening: Impact Beyond Words. His research spans thousands of professionals across industries, uncovering the science behind what makes someone a truly great listener.

His findings? 86% of people are stuck in distracted listening — checking phones, thinking ahead, or caught in their own assumptions. Meanwhile, top-performing CEOs and sales leaders operate differently. They listen with intention, silence their own thoughts, and hear what’s not being said.

The good news? Great listening isn’t a talent — it’s a skill you can develop. Let’s break it down.

The 5 Levels of Listening

Most people think listening is about hearing words. That’s just Level 2 on Trimboli’s five-stage model. To truly listen, you need to go deeper:

Listening to Yourself — Before you can listen to others, you need to silence your own mental distractions. Are you truly present, or are you just waiting to speak?

The insight: The biggest barrier to listening isn’t external noise — it’s the voice in your own head. If you’re already forming a response before the other person finishes speaking, you’re not really listening. Practice pausing your internal dialogue before engaging in conversations.

Listening to the Content — This is where most people stop — hearing words but missing deeper meaning.

The insight: Surface-level listening is common, but it can lead to misunderstandings and missed opportunities. Instead of just registering words, ask, “What is the real message behind what’s being said?” Repeating or summarizing key points can ensure that you’re absorbing the actual content.

Listening for the Context — What’s influencing the conversation? The speaker’s emotions, body language, and past experiences matter just as much as their words.

The insight: Words don’t exist in isolation. A person’s tone, pace, and nonverbal cues provide the full story. Are they hesitating? Do they seem tense? Understanding their emotional and contextual state can reveal hidden concerns or deeper truths.

Listening for What’s Unsaid — Most important insights aren’t spoken directly. Great listeners hear beyond words to identify underlying concerns and motivations.

The insight: Silence isn’t empty — it’s full of meaning. People often struggle to articulate what they truly mean. Instead of rushing to fill pauses, use them to observe and uncover what isn’t being said. Try using phrases like “Tell me more” to encourage deeper reflection.

Listening for Meaning — True deep listeners clarify, ask better questions, and uncover the real issue behind what’s being said.

The insight: Miscommunication kills productivity, deals, and relationships. Instead of assuming you understand, ask clarifying questions. A simple “What do you mean by that?” or “Can you expand on that?” prevents assumptions and ensures you’re solving the right problem.

Three Simple Fixes to Instantly Improve Your Listening

1. Silence is Your Weapon — The fastest way to get deeper insights is to pause. After someone speaks, hold silence for a few extra seconds. People naturally fill silence with more important thoughts, often revealing what they truly mean. Use this question: “What else?” It invites people to dig deeper.
2. Remove Distractions — You can’t listen deeply if your phone is on the table. Research shows that even having a phone in sight makes conversations shallower. Put it away. Pro tip: If you want full attention in meetings, take the lead — turn off your phone first, and others will follow.
3. Master the Follow-Up Question — Trimboli’s research found that most people interrupt after 11 seconds. Instead of jumping in, ask better follow-ups:

These questions deepen the conversation and uncover insights others miss.

The Business Case for Deep Listening

This isn’t just about being a better conversationalist, according to Trimboli. Deep listening makes you money. Here’s how:

• Sales Teams Who Listen Close More Deals — Research shows that top-performing sales reps talk 43% of the time and listen 57%. Average reps? They talk 70%+ and listen less than 30% — killing their chances.
• Leaders Who Listen Build Stronger Teams — Employees who feel unheard are 4.6x more likely to quit. Want to keep top talent? Listen more.
• Negotiators Who Listen Win More — FBI hostage negotiators rely on silence, strategic questioning, and deep listening to save lives. If this approach works in crisis situations, imagine what it can do for your business deals.

Trimboli’s Listening Challenge

Think you’re a good listener? Put it to the test. For the next 48 hours:

1. When someone finishes speaking, count to three before responding. Let silence do its work.
2. Ask “What else?” before moving on. Most of the gold comes after the first response.
3. Turn your phone off in your next conversation. Watch how the dynamic shifts.

Master this skill, and you’ll see the difference — in your sales, your leadership, and your relationships. Try it, then comment on this piece with what you learn. The community would love to hear how it works for you.

Until next time,

— Ryan

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Ready for more?

Catch Oscar Trimboli’s interview in its entirety on Eggs! The Podcast.

Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.

Path Picks

Cool stuff to help you forge your path to greatness.

Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R

Reading list

Want to learn more about developing and applying grit and resilience? Here are some great books that will help you forge your path.

• Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones by James Clear — A highly acclaimed book on habit formation, focusing on the small changes that lead to remarkable results. Oscar referenced it as the best-written business book he’s read, emphasizing the importance of breaking habits into their smallest components for lasting change.
• How to Listen: Discover the Hidden Key to Better Communication by Oscar Trimboli — Oscar’s latest book, expanding on his deep listening framework with research-backed strategies to improve personal and professional communication.
• Deep Listening: Impact Beyond Words by Oscar Trimboli — A foundational book on the power of deep listening, explaining the five levels of listening and providing practical tools to enhance one’s ability to truly hear and understand others.
• Deep Listening — Impact Beyond Words: Paperback Book & Practice Cards by Oscar Trimboli — A set of practical tools designed to help individuals and teams develop better listening habits through exercises and activities.
• Headspace App — A meditation and mindfulness app that includes guided breathing exercises, helping listeners improve focus and presence.
• Insight Timer App — A free meditation app that offers guided breathing and mindfulness exercises.

More to explore

Personal Website: https://www.oscartrimboli.com

LinkedIn Page: https://www.linkedin.com/in/oscartrimboli

YouTube: https://www.youtube.com/channel/UC_kkHeR0dGfAZGQ6AGHCvvg

Work with me

Ryan Roghaar — Fractional CMO/Creative Director/Art Director: https://rogha.ar/portfolio R2 — Creative Services for Agencies and SMBs: https://www.r2mg.com

Eggs! The Podcast: https://www.eggscast.com

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