Why Most Leaders Aren’t Really Listening—and What to Do About It
Leadership programs spend plenty of time helping people speak more effectively: how to present, motivate, and deliver feedback.
But much less time is spent on helping them listen.
A 2015 study found that while 78% of accredited undergraduate business schools list “presenting” as a learning goal, only 11% identified “listening” (Harvard Business Review).
That gap carries over into the workplace. And according to Oscar Trimboli, author of How to Listen and host of the Deep Listening podcast, most people don’t listen as well as they think they do.
The Listening Gap
Trimboli’s research shows that two-thirds of people are stuck at the very first level of listening: not focused on the speaker at all but caught in their own internal distractions. Another 30% operate at level two, where they hear the words but miss the context, emotion, and meaning.
That listening gap shows up in real ways across organizations:
- Misalignment and confusion
- Longer, less productive meetings
- Resistance to change
- Shallow or performative team conversations
- Lack of psychological safety
Listening Is a Leadership Skill
Oscar’s five-level framework reframes listening as a learnable skill, not a personality trait. And it’s not about mastering all five levels immediately. In fact, just moving up one level—say, from listening to reply to listening for context—can meaningfully shift how a leader communicates and connects.
It also repositions listening as something active. Not just paying attention, but shaping how a team builds trust, solves problems, and navigates change.
The Coaching Opportunity
Helping leaders become better listeners isn’t about quick fixes. It’s about developing the capacity to notice what they’re paying attention to, who they’re not hearing, and how the conditions of a conversation shape what’s possible.
Oscar offers one starting point: the process question.
“What would make this a good conversation?”
It’s deceptively simple, but powerful when used with intention. It helps set shared expectations, signals respect and opens the door for clearer communication. But knowing when and how to use it isn’t automatic. It requires presence, practice, and a mindset shift.
That’s where coaching comes in.
We help leaders move beyond the tool itself and into the habits that make it effective: creating space, noticing cues, and shifting the dynamic from reactive to intentional.
Through consistent reflection and real-world application, leaders build the discipline to listen with more clarity and to lead with more impact.
Listening as a System Skill
Oscar also reminds us that listening isn’t just individual, it’s organizational.
In high-performing teams, everyone listens to everyone. Not just to the person with the title. Not just to the loudest voice.
That’s why executive coaching so often starts with the individual, but must eventually scale to teams and systems. Because cultures are shaped not just by what leaders say, but by how they listen, and who they listen to.
If you’d like to explore how executive coaching can help you or your leadership team build deeper listening capacity, let’s talk!
🎧 Listen to the full episode with Oscar Trimboli on The Future of Teamwork!
Learn how the five levels of listening can help leaders build stronger relationships, better teams, and more adaptive organizations.
