top of page

Be a Good Listener: 5 Key Challenges to Listening & How We Overcome Them

Updated: May 31, 2021

I want to be a good listener.

I believe in shared humanity, desire equality, and want to engage in both my relationships and society in a way that inspires connection.


Listening can be difficult.

To listen is to be vulnerable. It means we respect someone’s right to speak even when we don’t agree with it, but genuinely desire to understand their perspective. It means showing up in uncomfortable, awkward, and messy conversations because this is the ground of meaningful transformation.

In a polarized time, where media creates echo chambers and complex issues like racial inequality are at the forefront, our ability to listen is as important as ever. If we want to make a change, to be the change, then we need to listen.

The Transformative Power of Listening

A year ago I stumbled across the story of Daryl Davis an accomplished musician, activist, and author. His story has since become a guiding light in my own studies and practice around listening. His courage, compassion, and genuine desire for understanding is a testament to the capacity of the human spirit.

At ten years old Daryl marched with his scout troop during a parade. A group of men targeted and assaulted him with bottles and rocks. One of only two black children in his school, he had no idea why he was attacked until his parents told him - it was because of his skin colour. In that moment he formed a very simple question in his mind, “how can you hate me when you don’t even know me?”

Years later, after a gig, Daryl found himself sitting with a member of the Ku Klux Klan and his curiosity resurfaced. As he says in his TEDxCharlottesville video “Who better to ask that question?” This conversation lead Daryl to Klan leader, Roger Kelly. He wanted to understand the KKK’s motivation and had his secretary book an interview with Roger. Roger arrived at the hotel, surprised to see a black man waiting. With his body guard at is side, and side arm in it’s holster, Roger explained that Daryl was “indeed inferior due to the colour of his skin.” Daryl explains,

“I wasn't there to fight with him, I was there to learn from him where these perceptions came from. Because in order to address something, you have to learn how they got there in the first place. So I'm listening”

Over time Roger developed a great respect for Daryl. He reconsidered his ideologies and resigned from the KKK. Daryl has since converted over 200 Klansmen and is largely responsible for dismantling the organization in Maryland. This is the power of listening and curiosity in action.

“If you have an adversary, you don't have to respect what they're saying, but respect their right to say it. And have that conversation. We spend too much time talking about each other, at each other, past each other, and not enough time talking with each other. That is respect.” - Daryl Denis

Show Up

Let’s be real, we might not want to listen. We may think the person speaking isn’t worth our time or attention, or maybe we feel like it’s just to uncomfortable, or not important.


If we really believe in connection, transformation, and growing as a human then we need to show up and listen. Let it be messy, let it be uncomfortable, just show up! Turn off the distractions, get curious, and give the other person your full attention. This is the arena of growth.

5 Obstacles to Listening & How We Overcome Them.

We will listen imperfectly. Even with the best intentions we will screw up, say the wrong thing, get distracted, and probably unearth some uncomfortable revelation about ourselves. Still, is there any other way? Dominance, ignorance, and manipulation may create change, but it's respect, love, and connection that instil transformation.

Below are 5 obstacles to listening and how we overcome them. These challenges are complex and intertwined. Be gentle with yourself - this is a lifelong practice.

Challenge 1: Taking it Personally

When someone speaks it is directly related to their experience & perception. When we take things personally we equate their experiences, words, or insights as a direct commentary on our identity or worth. This creates a sense of threat and launches us into any number of defence mechanisms - defence, repression, manipulation, even aggression.The intensity of this involuntary response depends on our history, conditioning, upbringing, and personal traumas. This is why something as simple as a single word can elicit a strong physical and emotional reaction.

How do we overcome this challenge?

We can stop taking things personally by developing presence, noticing when we feel threatened, and learning how to override the instinctual fight, flight, or freeze responses. As we develop our ability to be with discomfort, we are able to respond instead of react - listen instead of taking it personally. These skills can be developed through practice, mindfulness, meditation, contemplation, and seeking out a professional help to overcome complex patterns or trauma.

Begin today

Notice the sensations in your belly, chest, and neck. The next time you have a conversation (* start with an easy conversation) stay present to these sensations while simultaneously listening to the other person speak. This will help you stay connected and present as you listen.

Challenge 2: We Make it About Us

The second challenge, much related to the first, limits our ability to listen by turning the attention of the conversation onto ourselves. It is often unconscious and habitual.

We may notice we are the only one speaking, or realize that we haven’t asked any questions of the other person. This might be a sign that we are making the conversation about ourself. If we are formulating our response when the other person is talking, looking for an opportunity to share our ‘advanced’ knowledge, or giving advice to ‘fix’ the problem without really responding to what is said, then we aren’t listening.

Another way we make it about ourself is reactive-empathy. Unlike healthy empathy, an necessary skill for communication, reactive empathy can be intrusive to the conversation. When we are overwhelmed by empathic emotions, feel guilty, or overly responsible about what is said we turn attention onto ourself and put the onus on the other person to make us feel better.

How do we overcome this challenge?

For the most part these tendencies are habitual and unconscious. Developing self awareness and genuine curiosity about the other person helps us to listen. As we become aware of the ways we make it about ourself we can begin to catch and change our behaviour. A skilled professional may also help us in transforming more complex challenges like reactive empathy.

Begin today

Take a look at the ways ‘we make it about ourself ‘listed above. Reflect on how/ when you exhibit these behaviours in your own conversations. Simply bringing awareness to these habits can begin to transform them.

Challenge 3: We Assume we Understand

When we assume we understand we disengage our mind from taking in new information. This assumption can be difficult to catch as it is by nature a blind spot - in order to see what we don’t understand we would need to understand.

There are several ways this can show up. We may respond to what we ‘think’ the person is saying, or get caught up on a superficial aspect, instead of meeting their real concern. We may think “I know”, or “I know this already” which disengages our mind and stops us from receiving new information. Even when we are able to empathically understand we may still lack the knowledge or experience to realize the full gravity of what another person is saying.

How do we overcome this challenge?

Intellectual humility goes a long way in listening. When we don’t need to have the answer or understand right away, we create space to learn, ask questions, and seek clarification. Marie Forleo suggests that when we think “I know this already” we shift our mindset to “what can I learn from this?”

Begin Today

Before responding in a conversation, rephrase the key elements of what you heard the other person say and ask, “did I get that right.?” Allow space for them to add or refine any details before speaking.

Challenge 4: We Think Too Fast

In his book ‘Thinking Fast and Slow' Daniel Kahneman demonstrates how intuitive (fast, automatic, & emotional) thinking leads to more cognitive biases then rational thinking, which requires more effort, time, and deliberation.

If we rely on intuitive thinking alone we are likely to oversimplify what we hear and fall victim to our biases such as; only hearing what affirms our beliefs, dismissing information that is challenging or confronting, assuming our experience gives the full picture of a situation, only trusting information from people we like, or only focusing on the positive.

How do we overcome this challenge?

We overcome thinking fast by slowing down and considering information from a wholistic perspective including a deliberate rational mind. When we take time to consider what is said, remain present to sensations and emotions, and rationally question our beliefs and assumptions we receive information that would be missed through intuitive thinking alone.

Begin Today

Pause for ten seconds before responding and allow yourself to digest what you heard. This can help temper reactive responses while also giving time for the speaker to add any layers or additional information.

Challenge 5: We Expect the Speaker to Speak a Certain Way

It’s hard to listen to some people! Maybe they’re rude, blunt, harsh, or judgemental. However, if we dismiss these people outright we lose the chance to understand their perspective. Every person has a story, and every story gives insight into why that person is who they are.

Some of the best feedback we get comes in a not so pretty packages. An angry client or friend may speak in harsh words, but if we get past their initial language and stay present, we might uncover invaluable information. Choosing to listen means listening to the person as they are.

How do we overcome this challenge?

Engage with people, particularly those outside your bubble. Start where the stakes are low. Talk to the person in the supermarket, or the cashier at the drug store. Become genuinely curious in the stories of people’s lives, their opinions, and world views. As you widen your scope you will hear people talk in many ways and become comfortable with different types of language. Over time you may discover that there is much more being said then the language that is used.

Begin Today

Have a conversation with someone you find a little hard to listen to. Choose to listen and become genuinely curious about them. What do you learn? Do they speak differently to you when you engage them this way?

Listening is a Life Long Practice

Listening is a practice. It isn’t always trendy and may not ‘fit’ with the expectations of our family, culture, or societal pressure. But, it is a foundation for shared connection, emotional maturity, and meaningful personal and societal transformation.

As this is a lifelong practice be kind and patient with yourself. Self care and acceptance go a long way in creating the endurance and passion to engage life and people in their complexity. Showing up is the hardest and most important aspect of listening. Let it be messy, let it be awkward, but keep the conversation going! Do the work and support yourself through community, meditation, spiritual or relaxation practices, or anything that brings you laughter and joy.

Thank you for listening. I deeply appreciate you taking the time to read this blog and contemplate what it is to be a good listener. I invite all feedback, comments, insights, and thoughts as I am committed to learning and listening as well.

About the Author

Amy Thiessen is an international teacher, coach, & musician who focuses on helping individuals connect to their confidence, purpose, & self esteem through voice & communication. Offering a holistic approach Amy helps individuals uncover & overcome their unique blocks around voice & communication, connect to their self esteem & purpose, & ultimately express themselves in a way that is empowered & impactful.

Want More?

1:1 coaching is the fastest way to overcome your blindspots & find deep & more impactful expression. Book a FREE consult to see how In Resonance Coaching can support your full expression today!.

Links & References

2,054 views1 comment
bottom of page