8. The Art of Deep Listening

Many people think that they know how to listen perfectly well, but in fact, for a variety of reasons, they are poor listeners. Why so? The factors vary depending upon people’s backgrounds, histories and temperaments, but chief among them are:  

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  • They are self-deceived or unconscious: they think that they know how to listen just fine, when in fact they do not.

  • They are too weighed down, and distracted, by inner baggage (anxiety, fears, insecurities etc.) to be sufficiently present for proper listening.   

  • They have overcrowded and constantly active, and reactive, minds.  

  • They are egoic or prideful, and think there isn’t much need for listening, since they already know – either most of what’s useful or more than most. 

  • They are so self-driven, ambitious, living in a hurry, that they scarcely have the presence, or the time, to properly pay attention.

  • They are blinded by being in charge, by rank, money, or power.  

The obstacles to attentive and superior listening are in fact more numerous than we might imagine, which is precisely why it is a rare quality. It is rare enough that keen observers of the human condition can spot people who have this faculty, one in fact that is honed through on-going practice in the art of deep listening.

Most people do not listen with the intent to understand; they listen with the intent to reply.
― Stephen R. Covey, Educator, author and businessman


Attentive listening is an essential attribute of superior leadership, in all sorts of ways. A leader must take good care to develop very finely tuned ears, to be very present, and to absorb, to a high degree, lots of incoming and pertinent information. Here are just a few examples that show just how critical this leadership faculty is:   

  • Listening to staff members and superiors: their words, thoughts, emotions, directives, plans etc. 

  • Listening to our deeper selves, in the work context: our thoughts, minds, feelings, plans, distortions, weaknesses, strengths etc.

  • Listening to customers: their complaints, critiques, requests, desires, future needs.

  • Listening to organizational dynamics and politics.

  • Listening to competitors, to the industry, to the larger market conditions.

As this short list makes very clear, listening is not just about hearing the words and sentences, about getting content straight, about having conversations with people. If it were a simple as that, we would all be excellent listeners indeed. 

Most of the successful people I’ve known are ones who do more listening than talking.
― Bernard M. Baruch, Financier, philanthropist, and presidential advisor

The art of listening is about being deeply present to the situation at hand, and about learning how to become a finely tuned recipient of the various streams of information that are coming our way: the top level contents or words certainly; the underlying feelings and desires; the character and temperament of the people we are dealing with (subordinates, superiors, clients); the larger group dynamics (when applicable); our own feelings, biases, weaknesses, strengths, presence in the interaction; the larger organizational meaning of the communication or meeting; the bigger picture into which everything fits (our industry, market conditions, societal trends etc.).


In short, attentive listening is a Jedi skill. And no aspiring or accomplished leader can go without learning, and practicing, it. Indeed, once you commit yourself to the art of deep listening, you will be amazed at just how much you will learn and expand as a leader.


Putting it into Practice 

  • Practice attentive listening every day. 

  • Make a point to regularly speak a good deal less than you are accustomed to.

  • Learn about artful communication and listening (from books, workshops, colleagues, mentors and advisors).

  • Become aware of, and reduce, your own psychological transference and mental projections during communications.

  • Take on a deep breathing or meditation practice, which helps to calm and ground the mind.

  • Attempt to receive information without reacting or judging right away, namely: listen, observe and suspend judgement for a time.

  • Practice the Stoic Discipline of Judgement, which greatly enhances attentive listening.

  • Work to reduce your own inner baggage and mental turbulence, via psychotherapy or philosophical counselling.   


ART OF LEADERSHIP ESSAYS