The most comprehensive listening book

Creator of the Apple award-winning podcast

Deep Listening,
Oscar Trimboli

offers his research-backed keynotes, workshops and programs to organisations who want to take their performance to the next level.

To find out more about Deep Listening keynotes, workshops and programs

What’s the cost of NOT listening?

Communication isn’t just about what you say, it is 50% speaking and 50% listening. Most programs about effective communication focus on speaking with influence and leading change by setting a compelling vision, yet over 93% of change initiatives fail. There is a missing ingredient – leaders who listen. 

Only 2% of leaders have ever received any training on how to listen. 

However, leaders typically spend 64% to 83% of their day listening. The more senior your role, the more critical listening is to your career progress. 

If communication is 50% speaking and 50% listening, why is listening NEVER taught in leadership training programs? 

It’s like teaching a leader to run with only their right leg. It’s unbalanced and it’s exhausting running around in circles frustrated that you have made no progress. 

Through keynotes, workshops and organisational programs that leverage the Deep Listening research, you and your teams will have the tools for ongoing, sustained listening success. 

  • Increase profitability by minimising duplicate costs and effort caused by confusion and conflict 
  • Dramatically reduce project costs by asking the right questions upfront 
  • Attract and retain employees by listening to what they have to say as well as the unsaid 
  • Mitigate negative publicity in the media 
  • Get ahead of the competition by serving customers better 
  • Anticipate rather than react to the regulators in your industry 

The Five Levels of Listening

At the core of Deep Listening is the concept of the Five Levels of Listening. These five levels describe the hierarchy of listening. Each level is foundational. You need to be proficient at the previous level to effectively more to the next level.

The Four Villains of Listening

There are four villains when it comes to poor listening.


The Dramatic Listener

You love creating drama and exploring every element of the discussion. Rather than helping the speaker progress, you get stuck in the detail and dissecting the historical events and patterns that have led you to the discussion. You are so engrossed and engaged in the story that you become completely preoccupied in the theatre of the drama.


The Interrupting Listener

You’re so focused on finding a solution to the problem that you finish the speaker’s sentences for them. You feel they are moving too slowly in describing the issue, so you listen with the intent of solving, rather than their intent of being curious. You interrupt and interject, creating all kinds of confusion. You are busy solving problems the speaker hasn’t yet verbalised.


The Lost Listener

You’re in your own mind rather than in the conversation. You are so absorbed with your self-talk you don’t create enough space for the dialogue to land in your mind, you are so busy thinking about your last thought or your next thought that you can’t focus on the discussion. You are lost before you even turn up.


The Shrewd Listener

You’re too busy trying to solve the issue before listening to the explanation. You might be shrewd enough to wait patiently and not interrupt the speaker, but you are anticipating the future, trying to solve the problem before you’ve heard it or understood it all. You have forgotten to be present and to listen completely.

Any one of the villains can be at play for anyone at any time. Listening is situational and relational, meaning we listen
differently in different contexts and scenarios. For instance, you will listen differently to a customer compared to your peers. You will listen differently to people in the finance department compared to the legal team.


Think about the last conversation you had? Did one or more of the villains show up for you?

What others say

“Oscar identifies the behaviours we all need to practice to become effective communicators, leaders and influencers – it’s the lost art of listening.”

~ Dominic Price, Head of R&D and Work Futurist, Atlassian

Impactful Keynotes. Insightful Workshops. Subtly Powerful Work.

“Oscar is the antidote to the motivational rah-rah keynote. He opened our team conference with an amazing session that helped our team to build the foundational skills of listening. It transformed the state of the room and how we work together since.” 

– Jane Murray – Chief People Officer, Estia Health Limited

“Having Oscar open our event was the best decision we made. We arrived in a state of hype, manic energy and rush and were guided to a space of being open, curious, listening, leaning forward, engaged.”

 – Dr. Jason Fox

Sustained Results. Powerful Teams. Attuned Leaders. “Oscar gives teams the awareness and skills to have real conversations through Deep Listening. The way that Oscar has helped our team to listen has led to sustained results that have stood the test of time.”    

Erin Cramlet – Senior Director, Human Resources, Stryker South Pacific

“It’s a rare skill to hold the attention of our whole organisation after a full day of training. Oscar captivated, educated and challenged us.” 

 – Robin Tang, Brother Australia Limited

“Oscar gave us the ammunition of deep listening to take back into the workplace. Oscar provides inspiration, clarity and definitely an element of difference.”    

– Debbie Ireland, Managing Director, ShareThePoint Ltd.

“Oscar was thoroughly entertaining and engaging. We were engrossed and left feeling illuminated with a whole new level of awareness for us and our customers.”

– Eileen Puse, Qualtrics Asia Pacific & Japan

Featured Podcast Episodes

Listen to the Apple Award Winning Deep Listening Podcast

To find out more about Deep Listening keynotes, workshops and programs