The Art of Meaningful Conversations
Great conversations are opportunities to learn and feel
“Everybody’s talkin’ at me
I don’t hear a word they’re sayin’
Only the echoes of my mind”
— Fred Neil, 19661
When’s the last time you had a really good conversation? A great conversation?
I’m talking about an exchange where you and the other person are doing more than swapping dialogue: a more intimate, profound discourse.
There’s a concept known as the Great Conversation, in which thinkers and writers are constantly building on the ideas of those who have gone before them, and it was described by Robert Maynard Hutchins in the first volume of the Great Books of the Western World series:
“The great books were written by the greatest liberal artists. They exhibit the range of the liberal arts. The authors were also the greatest teachers. They taught one another. They taught all previous generations, up to a few years ago. The question is whether they can teach us. To this question we now turn.”
Read that quote again.
At its most basic, a conversation helps us to learn. But to learn we need to be ready to receive and process information. All too often, we see people who delight in transmitting information to others, but don’t care for the return volley.
The Power of a Conversation
In my time as an executive at Ford, I introduced our CEO Alan Mulally to social media — particularly Twitter, where we had a number of Q&A sessions. He was fascinated by the idea of real-time interaction with customers, fans, and the general public and was eager to hear what people had to say.
He expressed the realization of what this new (at the time) platform was able to unlock for the company and for individuals:
“I can remember the first time we were talking [about Twitter] and he was explaining about the power of being able to have a conversation. And boy, was he ever a visionary. He is just a fabulous leader.”
In a future issue, I’ll share a story with you about how I turned around the C-suite executive who was the biggest skeptic of my work.
Be an Illuminator
In How to Know a Person: The Art of Seeing Others Deeply and Being Deeply Seen, David Brooks attempts to enlighten us on having better conversations. He prepares us by recommending that we should all become what he calls Illuminators: those who light up and who bring out the light in others as well.
You can’t do this if you’re inherently incurious, though:
“If we’re going to become Illuminators we need first to ask questions and engage with answers.”
How about that? That’s the same concept as the Great Conversation. It’s the Socratic method, writ large.
Illuminators go further than asking questions and listening, though. According to Brooks, some of their features include tenderness, reactivity, active curiosity, affection, generosity, and a holistic attitude.
More simply put, the art of a great conversation goes beyond listening and extends to empathy: being able to truly understand someone else.
“What the eye sees better, the heart feels more deeply.”
— Robert Kegan, 1982
Making people feel seen and including everyone is one of the hallmarks of the Working Together Leadership and Management System that Alan Mulally established and that I use in my executive coaching practice.
It means taking the time to give dignity to the people in your orbit, showing them they are worthy of your attention.
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“What is essential is invisible to the eye.”
— Antoine de Saint-Exupéry, 1943
Going Deeper
When we engage more deeply with people, we become alchemists who turn a dull leaden conversation into a shiny golden moment of connection.
In order to unleash this precious metal, we need to be curious; we need to go beyond dual monologues or two people talking at each other and learn how to listen and feel what the other person is saying.
Brooks put together a list of non-obvious ways to become a better conversationalist:
Treat attention as an off/on switch, not a dimmer: either give someone your full attention or don’t bother.
Be a loud listener: be reactive to your conversation partner; let them know you’re engaged.
Favor familiarity: land on something the other person is most attached to.
Make them authors, not witnesses:
Don’t fear the pause: silence is a chance for reflection, not a moment that needs to be filled.
Do the looping: repeat back to them what you’ve heard.
The midwife model: you’re not giving birth to the conversation, but you’re helping someone else bring one into the world.
Keep the gem statement at the center: find a truth you both agree on and focus on that.
Find the disagreement under the disagreement: rather than restating your point, ask “Why, at heart, do we disagree?”
Don’t be a topper: it’s not about you; don’t try to outdo someone else with your own examples as you try to relate to them.
Caring about other people (something all great leaders do) means trying first to understand them, then trying to be understood. And that begins with conversations.
The best conversations are a dance we undertake together; a mutual exploration of what we’re thinking and feeling, set to the music we both hear.
Awkward silences
What is it about lulls in conversation that make them so very uncomfortable? It has to do with how we connect with each other (Aeon)
True contact is found in silence
There’s a strange intimacy in the best kinds of silences (Psyche)
The most undervalued skill in effective leadership
Often dismissed as a soft skill, listening is a strategic tool and a pillar of effective leadership. ()
How to strike up a friendly conversation
It can be awkward at first, but there are specific methods you can use to spark an enjoyable chat with just about anyone (Psyche)
Yes, and your bedside manner
Mayo Clinic medical residents take improv classes to improve patient relationships (NPR)
Humanity has a place in AI
has a touching story of being truly seen (at least for a fleeting moment) in a work setting. Her story is a powerful reminder that treating employees as cogs and systems in governance misses this crucial acknowledgement of our humanity. () 
Two items to add to your bookshelf:
How to Know a Person: The Art of Seeing Others Deeply and Being Deeply Seen by David Brooks, Random House. New York, 2023
The Evolving Self by Robert Kegan, Harvard University Press. Cambridge, 1982
Additional Timeless & Timely Resources
These extras are exclusively available to members the & Guild — our paid membership tier. Become a member today and unlock these tools to help you improve.
“How to Get Better at Small Talk”: A secret weapon to help you get more comfortable and to make other people chatty
“The Sound of Silence”: becoming comfortable with and paying attention to the quiet moments in our lives
Plus, check out entire sections on Empathy, Humility, and Listening.
There’s so much to learn,
I know you were expecting Harry Nilsson’s name to be here. He recorded Neil’s song in 1969 for Midnight Cowboy, getting it up to No. 6 on the Billboard chart.
Hey Scott, as always, great post, and thank you so much for the inclusion!