✅ Toby's Takeaway 🤖 Exercises 📹 Video 💡Big Ideas 💬 Best Quotes 🛒 Buy on Amazon
📚 Should You Read This?
Toby's Rating: 7/10
Yes, How to Listen by Oscar Trimboli is perfect for leaders who want to unlock deeper, more impactful conversations. The book provides an actionable framework that shows how better listening can strengthen professional relationships and drive results. It’s ideal for leaders who want to reduce communication breakdowns and improve team engagement by transforming their listening skills.
✅ Toby's Top Takeaway From How To Listen by Oscar Trimboli
I asked a leadership team to rate, on a scale of 1-10, how they would rate themselves as a listener compared to others.
I also asked a subset of their teams to rate their leaders' effectiveness at listening.
The result may not surprise you.
The vast majority of leaders on the leadership team rated themselves above average.
In contrast, only 10% of their direct teams felt the leaders showed effective listening.
It's not unique to listening. I ran a similar exercise with another leadership team, but instead, I asked them to rank their coaching skills.
The same result: Most leaders felt their coaching skills were above average, yet the teams they worked with felt the coaching they received was below average.
There is a cognitive bias to explain this behaviour: illusionary superiority. This is the tendency for people to rate their abilities, qualities, or behaviours in an overly favourable way, often attributing positive outcomes to their actions and negative outcomes to external factors.
In How To Listen, Oscar Trimboli says:
The first listening barrier is self-awareness.
I'd broaden it to "the first leadership barrier is self-awareness."
Without it, leaders will be convinced that "I'm not the problem; everyone else is."
The takeaway for leadership development is that few skills can be developed without requiring increased self-awareness.
You cannot become a better listener without increasing your self-awareness.
The question then becomes not how to become a better listener, coach, leader, or manager but how to become more self-aware.
Oscar shares this exercise, which can be an easy first step.
Read instructions 1 to 5 completely before you commence.
Focus on a blank space, a wall, or some paper for the next three minutes—not a screen. It would be even better to close your eyes during this exercise.
Notice your breathing; is it slow, fast, light, or heavy?
Bring your attention to yourself and ask yourself: What am I not listening to in myself?
Switch your phone to "do not disturb" and set your alarm for three minutes.
Ask yourself, "What am I not listening to in myself?" Do this for three minutes.
Please commence now.
I'm curious: what has helped you develop self-awareness?
🤖 Turn This Book Into Action
Despite reading this book, I still have a problem. I’m not converting the knowledge into action. To solve this problem, I’m turning to the solution everyone is looking for: artificial intelligence. I’ve developed a set of AI tools to turn knowledge into action.
💡 3 Big Ideas From How To Listen by Oscar Trimboli
Five Levels of Listening - Oscar Trimboli categorises listening into five progressive levels: listening to oneself, to the content, to the context, to the unsaid, and finally, to the meaning behind words. This layered approach helps leaders understand what is being said and uncover the underlying concerns, motivations, and feelings. Mastering this process can lead to more informed decision-making and create an environment where team members feel genuinely understood.
The Power of Presence - Effective listening demands more than just hearing words—it requires entire presence. Trimboli stresses the importance of mentally “tuning” oneself to reduce internal distractions. For leaders, being fully present means setting aside personal biases and preoccupations to focus entirely on the speaker. This deep presence helps build trust and enables leaders to foster richer, more meaningful interactions.
Listening as a Tool for Problem-Solving - Oscar Trimboli explains that effective listening can identify and resolve conflicts more swiftly and accurately. Leaders can use listening as a diagnostic tool to catch early warning signs of issues within their teams or projects. Listening beyond words allows leaders to capture nuances in tone and context that can reveal unspoken challenges, helping to address problems proactively.
💬 Best Quotes From How To Listen by Oscar Trimboli
Listening is the willingness to have your mind changed.
Western society is biased towards heroic and charismatic speakers.
The five levels of listening:
Yourself
Content
Context
Unsaid
Meaning
When asked how they would rate themselves as a listener compared to others in their workplace, 74.8% of respondents considered themselves above or above average. When asked to rate the listening of others, only 12.1 % chose well or above average. What does this mean? It means we each think we are much better listeners than others. The first listening barrier is self-awareness.
There is no universal and shared understanding of how to listen effectively.
In 2015, Google created a process: when a meeting is large or has more attendees, it begins with a short pause. Attendees were invited to switch off their devices and notice their attention and where they wanted it to be during the meeting.
Treat silence like a complete word: listen to their pause's beginning, middle and end.
The backstory needs to start at the beginning - at the very beginning of the issue, not where the speaker commences.