5 Simple Steps to Leading Better by Listening Better

Gracy Obuchowicz September 5, 2016


A big part of learning to listen well is giving up control of what will be said or where the conversation will go. This may sound easy, but it’s surprisingly hard for a lot of us.

My listening pitfalls begin with my desire to be favorably perceived. I want to look competent, so I start to think about what I’m going to say next. The more I want to impress the person I’m talking with — like a potential client — the less I tend to actually listen.

It has taken me a lot of practice, but I’ve learned that if I am feeling insecure, it’s a good sign that I need to listen more deeply. Now I trust that no matter what happens, if I listen well, I will know the right thing to say when it’s my turn to talk. Sometimes after deep listening, the things that come out of my mouth surprise me. They are often less about what I want to say and more about what the person actually needs to hear.

In a world where very few of us feel authentically understood, real listening is noticed and rewarded. Often, my clients tell me they signed up for my programs because of the quality of listening they experienced during our first conversation. Speakers know when they are being heard and when they aren’t. Listening well can help you increase intimacy and gain immense amounts of trust. At a time when many people say they can’t trust their co-workers, these interpersonal skills will pay off in both obvious and subtle ways.


I notice that I also tend to stop listening when I want to regulate the emotional quality of the conversation. It’s a really vulnerable thing to listen undefended, especially at a moment when someone might give harsh feedback. Who wants to hear that? Why not just zone out? It’s way easier to think about what I’m going to eat for lunch than to listen deeply to someone who may hurt me.

It’s natural to want to shield ourselves from criticism. However, receiving feedback — both the positive and constructive kinds — is essential for personal and professional growth. And we can’t receive feedback if we don’t listen. I see this fear of receiving feedback (and lack of giving feedback) as one of the biggest blocks to professional development. So I have to walk my talk. In order to grow as a business owner and a person, I always ask my clients and collaborators for feedback.

However, I also know when I am emotionally prepared to listen to negative feedback. If I have asked for written feedback, I wait until I am feeling pretty stable before I dive into the answers. When I begin working with a new collaborator, I like to have a conversation about feedback. My rule is that they are allowed to give me as much negative feedback as they can think of, but they must warn me that it’s coming. That way I can check in and see if I am actually able to receive the lessons they are offering, and if not, suggest waiting for another day.


We usually begin listening with good intentions. An employee comes to us distressed. We sit across from her, make eye contact, and let her know it’s OK to begin telling her story. It’s time to listen!

Then she gets five sentences in, and suddenly we totally get what she is saying. We actually went through the same thing last year! Our next move is to let her know how much we relate to her story and perhaps help her solve her problem. So we interrupt her and begin to tell our story. Suddenly we are no longer listening.

Relating is a deeply important part of connection. It helps us feel compassion for others. The issue is that when we over-relate, we are not listening. By switching from listening to relating, we’re cutting off the possibilities of the new insights that can arise when we discover that her story is more nuanced than we imagined. Maybe our advice will help her a lot, but my guess is that deeply listening to employees (and coworkers and friends) will help both them and us a whole lot more.

If you struggle with over-relating, start noticing how it feels when you’re in conversation and the other person cuts off your story to tell their own. Does that change the course of the conversation? Did you get to fully express yourself? Although you may enjoy hearing about someone else’s similar story, you might still not feel heard. Once you begin noticing how this feels from the receiving end, it will make it easier to practice restraint and bite your own tongue when you want to say “Oh, me too!”

“I’ve learned that if I am feeling insecure, it’s a good sign that I need to listen more deeply. Now I trust that no matter what happens, if I listen well, I will know the right thing to say when it’s my turn to talk.”


I once took a communication-skills workshop where our task was to partner up and take turns speaking for five minutes about a problem we were struggling with. As the listener, we were not allowed to say anything or give any kind of physical clue that we were relating. This meant no encouraging nodding, no sympathetic clucking, no deep sighs — we just had to make emotionless eye contact and hold space for someone else to speak.

This was extremely challenging for me as both the speaker and the listener. When I was speaking, I wanted the signs of approval that my speaking was effective and that I was understood. As the listener, I wanted to let the other person know that I heard her and understood her, and that she could keep going. It felt cold and awkward and impersonal — at least initially.

But within five minutes of being listened to by my partner, I’d solved my own problem. I knew the right action to take for a situation that I’d been stuck on for a while. And the person I was listening to also solved her problem. Despite the awkwardness, the effectiveness of our communication felt oddly effortless. As we thanked each other, I felt a fierce kind of intimacy with my partner. I realized it’s rare in our culture to find that kind of open space to really be heard.

I know it’s a big stretch to resist so much as nodding when someone else is talking. Actually, it can be kind of creepy unless you tell the person what you’re doing. But when you are listening, notice how your “active” listening might be getting in the way of true hearing. Perhaps your Herculean effort to show you are understanding someone is actually making them feel less understood.


If, after practicing a few of these deep listening skills, you still find yourself interrupting or spacing out, I suggest investing more time in listening to yourself. We can only give others what we are giving to ourselves. If your life is filled to the brim with other people’s ideas and opinions and needs, then the chances of you being able to effectively hold space for another person are small.

Learning to listen to myself has been quite a journey. As listening to myself usually means dealing with trickier emotions like anger and fear, it’s natural that I resist it. This is why I have to program time for it into my days. Some days this looks like 30 minutes of journaling in the morning. Other days it’s five minutes of meditation upon rising, while waiting for my hot water to boil. It can often be calling a friend who doesn’t over-relate and so can help me ramble my way to clarity.

Listening to myself is the best way I’ve found to be my own friend. When I’m feeling friendly to myself, my cup is full enough to offer some to others. I can listen to my coworkers and my other relations.

Listening is a rich way to live life because I can learn so much more than when I am just talking to fill space. I soak in knowledge and hold space for others’ breakthroughs. I grow so much in the process. Listening is simple, yet so effective and so very valuable. I can talk about it all that I want, but the proof is in the practice. So try it. Where can you listen more today?

Gracy Obuchowicz is a self-care mentor, workshop facilitator, and retreat leader in ever-stressed Washington, DC. She is a recovering perfectionist who has learned to live a life of real self-care and self-love. Through her self-care coaching programs, she helps overwhelmed professional women transform their lives. Get more of her essential self-care tips at selfcarewithgracy.com.

Social Entrepreneurship / Stakeholder Capitalism
Join the SOCAP Newsletter!